yes, you are awkward … and yes, it’s okay

I love awkwardness — my own, other people’s, all of it. There’s little I enjoy more than dissecting a mortifying moment with a close friend (“What do you think they were thinking when that came out of my mouth?!” “They must have been so baffled by why you said that!”) or even speculating on hypothetical mortifying moments that haven’t even happened but could (a friend and I have spent entire meals laughing about the prospect of embarrassing things that haven’t even happened to us yet). It’s probably no coincidence that I write a blog that frequently trafficks in the embarrassing situations of others (like accidentally hugging your CEO in the office elevator, or spontaneously biting a coworker).

So I was beside myself with excitement when I found out that Melissa Dahl, the editor of New York magazine’s Science of Us, was writing a book about awkwardness — Cringeworthy: A Theory of Awkwardness. I recently got ahold of an advance copy and it is AMAZING, and she was nice enough to give me a copy to give away here (more on that in a minute).

Cringeworthy delves into when and why we feel awkward, and how we can move past it. You’ll learn about why it’s awkward to mix two groups of friends, where secondhand embarrassment comes from, and how to fight off a cringe attack — and there’s a whole chapter on awkwardness at work! (I’m interviewed in that chapter, and it’s probably my favorite interview ever.)

Melissa writes with candor and humor about her own experiences of awkwardness — and she seriously sacrifices for her readers by intentionally putting herself in awkward situations so that she can explore them in the book. She reads her teenage diaries live on stage, she does improv, she tries out a Tinder-like app for friendships, she makes herself network, and she has a hilarious account of her session with a professional cuddler (which she, quite understandably, sprints out of).

I love this piece from the intro and think it sums up the entire credo of the book: “The things that make you cringe are usually the things worth sharing, because they can help others feel less alone. … It’s an understandable reaction to flee the situation that makes you cringe, but what if you could teach yourself to tolerate it? You could, maybe, learn to use the empathy as a portal to compassion, for other people and for yourself. Looked at in a certain light, cringing because becomes a worthwhile feeling, an emotion worth exploring, not avoiding. Little humiliations can bring people together, if we let them. The ridiculous in me honors the ridiculous in you.”

This book is the book I always wanted to read! I want you to read it too.

To enter to win a free copy: Leave a comment describing the most awkward situation you’ve ever experienced or witnessed at work. I’ll pick the the winner at random (or rather, a handy WordPress random selector plug-in will). All entries must be posted in the comments on this post by Friday, February 16, at 11:59 p.m. EST. To win, you must fill out the email address section of the comment form so I have a way of contacting you in the event you’re the winner.

And if you don’t win this giveaway, I hope you will buy yourself a copy. If you like this blog, you will like this book.

* I make a commission if you use these links.

{ 1,261 comments… read them below }

    1. Ask a Manager* Post author

      Also, a reminder that entries need to include your email address in the email section of the comment form if you want to be able to win (otherwise I won’t be able to contact you to tell you that you did!). If you forgot, you can leave a reply to your original comment that includes it. (As long as you put it in the email section and not the comment itself, only I can see it.)

      1. romana*

        I was working with a male coworker and he’d pulled two foam spacers off a motherboard. When I was cleaning up the floor around my desk (I was kneeling) I looked up at him and said “Do you want these two soft squishy things?” I was not holding the spacers – still not sure what they’re really called.

        Same job, different incident: I’d decided the elevator was a good place to adjust my bra. The doors opened before I was finished. My boss was standing on the other side. He forgot where he was going.

        Same job; I was finishing up an install for a professor and I went to leave but suddenly couldn’t work the door handle. He came up behind me and politely showed me how it worked, as I was leaving I tripped over two plastic chemical buckets that were in the hallway.

        I still work there, believe it or not.

      2. Marti G*

        I wore dress pants and a blouse with a cardigan so I would feel comfortable and professional for a presentation. The awkward time came after when I removed the cardigan. I had walked to my desk to wind down and another manager came over to tell me how well I did. He also stated that I would make a great representative for the company and department. I was flattered and thanked him. I went to the rest room to freshen up and realized that the shell I wore underneath the blouse had created a static cling, and completely stuck to my body! I ran to my desk to put the sweater back on and still do not know what he actually saw. Awkward and a learning lesson I will never forget!

        1. Worked for Scrooge*

          Thanks for hosting this contest!

          The most awkward work situation I’ve had is a very odd company owner giving all the staff a Christmas gift of a roll of pennies. This was over 10 years ago and I still laugh wondering what the heck he was thinking.

          The awkward part was watching other Co-workers react. None of us knew what to do.

    2. Cajun2core*

      IMHO, the “duck club” letter writer should automatically win and get a copy of this book. Heck, her story should be in the book!

    3. spaceygrl*

      I meant to write this the other day when there was a question about clothing malfunctions or something like that…. I was about 25 and in a meeting with two very senior people: my boss, the VP and the CEO of the company. My boss and I were sitting in chairs in the CEO’s office facing his desk. I was explaining something and didn’t really notice, until later, that the CEO was hunched over his desk staring down at the spreadsheet I had prepared. My boss started talking and looked at me and his eyes grew wide and he looked down and then back up and kept talking. I was like “that was weird” and so I looked down and my v-neck shirt, which would normally be completely appropriate had gotten stuck on my fuzzy bra and a whole boob was sticking out of my shirt. Luckily, I was wearing a sweater I could pull around without having to adjust my shirt. That made me realize why the CEO wasn’t looking at me. I never wore the velvet bra to work again.

      1. TeacherOffTopic*

        I just Googled velvet bras. I had no idea they existed, and I’ve had boobs for almost half my life now!

    1. Snark*

      Sorry, got excited there. So, my most awkward work-related moment occurred when I was working alone, late at night, in my lab in grad school. I was very focused on my work, bent over a piece of equipment I was trying to fix, and I felt a hand land on my on my shoulder. I was dating a labmate of mine at the time, and she had a habit of giving me little pats and squeezes as we moved around the small space during the day. So I said, “hey, sweetie pie,” gave the hand a smooch, and realized that it was male and hairy.

      It was awkward with my advisor there for a bit.

        1. Snark*

          I guess he was just trying not to startle me while I worked with his expensive lab thingy, but….yeah, regrets were had by all.

          1. Hey Nonnie*

            I dunno about you, but an unexpected shoulder squeeze while working alone (or thinking I am) would achieve the exact opposite effect.

            I actually don’t startle easily — I have good hearing when it’s quiet. But I also have intense focus when concentrating, which tunes everything else out. If you DO startle me, you bloody well better duck, because there WILL be flailing and anything in my hands will probably smack your face.

        1. Specialk9*

          I dunno, I feel like that’s what you get for touching coworkers. It’s not exactly normal to just grab someone’s shoulder.

      1. bb-great*

        NOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOO (by which I mean YESSSSSSSSSSSSSSSSSSSSSSSSSSSSSSSSSSSSSSSSSSSSSSSS this story is AMAZING)

      2. ggg*

        This is good.

        My advisor was known for putting his foot in it, especially with female students. I will only tell my own stories:
        When I told him I was getting married, he said, “I think I should probably hug you. Should I?”

        Also when I finally graduated he said, “Well, we never thought we’d get here, did we?”

    2. Danger: Gumption Ahead*

      Back when I worked in private industry I handed my coat to the CEO as I walked into the Christmas party. There were 3 doors, 2 of which had coatroom clerks taking coats and one of which has upper management shaking hands. I had no idea what the CEO or the CFO looked like, so I walked through the upper management door and handed over my coat. Everyone had a laugh and it ended fine, but I was teased for at least a year after that

  1. Emi.*

    Well, I once had to listen to a coworker tell me about how much he and his friends wanted to watch Romeo+Juliet as teenagers, so they could see Kate Winslet shirtless. So that was pretty awkward.

  2. MuseumChick*

    Most awkward situation at work: When, while alone in the museum I worked at the time, a homeless man with mental health issues decided the day was to hot for clothing and processed to remove said clothing in the middle of our parking lot just in time for a visitor with his young daughter in tow to see.

  3. NYC Redhead*

    I work with philanthropists, and I was trying to say that a well-established nonprofit in our city was known for doing good but not pushy outreach, and I said, “XXX always touches their donors appropriately.”

    1. CoveredInBees*

      I worked at a nonprofit for a CEO who was not careful about talking about “touching” donors as in being in contact with them about our work and their interests. She also repeatedly talked about not being dressed when what she meant was “dressed up”. I was on a call with her and a prospective funder when she mentioned that she and I weren’t dressed. I jumped in to clarify she was referring to casual Fridays but I’m pretty sure I could hear the poor guy blushing.

      The funniest was when an attorney (thankfully, not me!) said, “Thanks, I love you too.” to a judge. He was distracted and said it in a way like he was ending a phone call with a loved one. The funniest part was that it took the judge a few beats to notice. I am certain that there was nothing going on between the two of them but they were very careful after that.

      1. Higher Ed Database Dork*

        My old boss was really bad about saying “touching the students” – we were a para-IT helpdesk at a university and it drove me nuts!

        Also the concept of “nudging” is huge right now in higher ed so I keep hearing people use “nudge” and “touch” interchangeably and it’s just always bad.

      2. chocoholic*

        I live in near-constant fear of telling an interview or some work contact that I love them. It is how I end most phone conversations with my husband.

        1. the gold digger*

          I have never said, “I love you” to my boss, but in heated discussions, I have, more than once, yelled, to my boss, who does not have the same name as my husband, “[Husband’s name], you are driving me crazy!”

          And he has called me by his wife’s name by mistake.

          1. Anonymoose*

            Ha!

            I have called a few (!!) bosses ‘Mom’ when trying to explain something while I’m frustrated.

            Habits – they kill us, sometimes, don’t they??

        2. Wombats for All*

          That happened with one of my new bosses. When I said um in response he had an “Oh Crap not again” reaction. Then he told me to never tell his wife as she’s convinced he says it to everyone else more often than to her.

          As an old mentor of mine used to say there are worse things to say than I love you.

        3. Princess Consuela Banana Hammock*

          My coworker used to do this often, especially at the end of the day or when she was distracted. It was usually after she’d finished talking to her fiance, and I always felt fremdscham for/with her.

      3. DG*

        Oh man, I’ve done the “I love you” at the end of a call with a co-worker before. Luckily, it was someone I was friends with outside of work, but I did laugh and turn bright red after it happened.

        1. Anne of Green Gables*

          My boss has done that to me more than once. I don’t think he realized it and I never said anything. I’ve heard him on the phone with his wife and know’s it’s the ending to the conversations with her. I laugh on the inside, though.

      4. Golden Lioness*

        I did this to my boss. It was my day off and he needed to contact me about an emergency at work. Before I hung up I said “see you tomorrow, I love you!”

        he was a cool guy, and teased me mercilessly about it.

      5. mrs__peel*

        My job involves participating in legal hearings via telephone. Although I haven’t said that (yet!) to a judge, I have heard all kinds of accidental/ inappropriate/ hilarious things on the phone during those.

        One of the doctors I work with has a talking parrot, who loudly announced “HI, BIG BIRDIE!” to a judge when she was on speakerphone for a hearing.

      6. PhyllisB*

        Bees, this is not an awkward work story, but talking about your CEO saying that she wasn’t dressed made me think of my mother. She says three things that crack me up. First one: “I couldn’t answer the door, I don’t have my face on!!” (No make-up.) “I went running outside to catch the garbage truck and realized I was standing there with just my feet on!!” (Barefooted.) ” I can’t go yet, my hair’s all over my head!!” (A big mess.) My sister and I always tease her mercilessly about these sayings, but I’ve found myself saying them from time to time.

        1. Daisy Avalin*

          My family (dad’s side) has always used ‘feet or ‘feets” to refer to shoes or socks, i.e. “We’re leaving in 5 minutes, go get your feet on!” My daughter argues with me now when I say it, because “I’ve already got my feet on, can’t you see?”, but she does find her socks/shoes to put on.

    2. TheAssistant*

      I worked for a fundraising director who encouraged all of the fundraisers to “love up on the donors”. She said it constantly. “Can’t ever love up on them too much!” “Have we done enough loving up?”

      She had this folksy charm that was disarming, even to a person (me) who is normally immune to that, so it was more funny than awkward. But I always hoped that nobody else slipped in saying that to an Actual Donor.

      1. Ruffingit*

        I have a boss now who says we’re going to “love on” our clients. Dude, you’re going to have to pay me A LOT more for that! ;)

    3. Elemeno P.*

      My former boss was so excited about an email he got to send once. He had to send an update about the teamwork on a new building that was going up. He wrote, “The erection is massive, and the whole team is trying to finish it off.”

      He knew EXACTLY what he was writing and it was hilarious.

    4. Jadelyn*

      I mean, if the alternative is touching your donors inappropriately, maybe touching your donors appropriately is actually a good selling point?

  4. Amber Rose*

    My boss was treating a supplier and ended up pinching his nipple because she thought it was funny to see him blush.

    That was so awkward I got second-hand embarrassment just listening to the story (it happened before I started here).

    1. Amber Rose*

      As for personal experience, how about the discussion of which Christmas tree ornament looked more like an… object of an adult nature? When we were decorating the office last year. Actually I’ve experienced more uncomfortable conversations but I don’t know how to explain them without moving into language that probably won’t make it through the filters.

      1. Amber Rose*

        I mean yeah, sort of. You have to understand that she’s been working with this guy for over a decade and they are relatively close, and they were drinking at the time. It was still crossing the line, but it was one of those crossings that is shrugged off as long as it doesn’t happen again.

  5. Marillenbaum*

    When I worked in college admissions, it was probably the time that I read an application essay about how the student in question had laughter-based incontinence, and how she was grateful for it because it meant she had so much to laugh about. Rule of thumb: keep bodily fluids out of your college applications (see also: the student who wrote their essay about contracting herpes).

    1. GetYaGritHeeere*

      I actually cringed reading that. The second hand embarrassment I’m feeling for both of them is so very strong.

    2. Todd Chrisley Knows Best*

      I’m really curious to know if they made it in or not. I’m assuming not, but I’m curious all the same.

    3. Competent Commenter*

      I don’t know, to play devil’s advocate, I feel like that student was showing that she had a medical condition she couldn’t control, and that she’d made peace with it in a graceful way at a very young age. How many people can say that? I agree I wouldn’t have recommended she pick this subject, and maybe the essay was written badly, but the topic itself seems like it has some strengths. If she’d been describing her hemophilia and how she coped with it, that would have been fine, right?

      1. Anonymoose*

        I agree (the first essay). Especially if she could tie it into what she wanted to study, I think it could be an excellent essay topic. Not all of our challenges are going to be pretty, I think holding that against her is actually small minded.

        Now, the second story…ya.

      2. Ani are you okay*

        If you are going to ask every student to describe a struggle they’ve had to overcome, I guess you will get ridiculous stories from the kids who have relatively easy lives.

  6. Mr. Programmer*

    I used to work at an American division of a Japanese company (this is relevant). I was able to get the job, partially because I studied Japanese at school, so even though it had lapsed some, I understood some of what was going on.
    One of the Japanese members of my team was on a conference call with Japan, which went well until the end. As he was hanging up, he was saying goodbye to people and when he should have said “Sayonara, Oka-san”, he ended up saying “Sayonara Okaa-san” (very minor intonation difference, but enough). Those of us who understood Japanese just stopped and stared at him as he turned bright red. Everyone else around just kinda looked around, asking what they missed.
    What he meant to say was “Goodbye Mr. Oka”. What came out was “Goodbye, mother”.

    1. EddieSherbert*

      That is extremely unfortunate… hahahaha. I’m dying from the second-hand awkward of these stories!!

    2. Amber Rose*

      Ahaha, that reminds me of an article from my favorite author who recounted the time he was trying to give an inspiring speech to his Japanese associates and mixed up the word ninjin with ningen.

      In other words, he told the room that they were all carrots, instead of people.

      1. Cherith Ponsonby*

        It’s particularly funny / confusing because “nin” and “jin” in context can both mean “person”!

        I studied Japanese intensively at primary school (long story) and when I was in first grade one of my language teachers used to tease me by calling me silly things in Japanese, and I’d pretend to get mad and deny it. So this one morning I met him in the corridor on the way to assembly and he said “Ohayo, ringo-chan” (“good morning, apple”) and I said I wasn’t an apple, and he apologised and said I was a ningen. And my Japanese vocabulary wasn’t really that big at the time but I was pretty sure he’d called me a carrot, so I loudly and indignantly replied “ningen ja nai desu” – “I’m not a person!”

        Some years later a different teacher was going over slang terms for one’s parents, and told us that while otousan and okaasan did indeed mean father and mother, they were childish to use in speech and you would generally use chichi and haha respectively. So overachiever me, knowing very well that you can often put an o- at the front of a word to make it formal, piped up with “so in a formal situation would you call your dad o-chichi?”

        No, no you wouldn’t, as the teacher managed to explain after a few minutes of uncontrollable giggling. Turns out o-chichi means boobs.

    3. Serendipity*

      I lived in Japan for a year when I was a teenager. When I was new and still learning Japanese I tried to make friends by giving my schoolmates compliments.

      Yeah, I mixed up ‘kirei’ for ‘kirai’ and ‘kawaii’ for ‘kowai’ .

      Turns out that instead of saying ‘you’re petty, I like you’ I was saying ‘you’re ugly, I hate you’.

      Much embarrassment.

      1. BeenThere*

        I studied Japanese from grade 8 to 12 and was lucky enough to visit for two weeks during that time, one week with host families in a rural town with Mt Fuji a short drive away. A dear friend of mine was also on this trip, upon seeing mount fuji on thenhorizon whilst on an outing with the family happened to also mix up kirei and kirai when she tried to exclaim how pretty it was. Her host family were initially horrified and she was confused followed by utter mortification! Fortunately sumimasen is one word you get drilled into your vocabulary when learning the language.

    4. the gold digger*

      Another Peace Corps volunteer in Chile once asked a waitress for a kiss instead of a glass – beso/vaso.

      I told the people at the bakery by my office that I was from Texas – that place with a lot of cowboys. Or bones. You know. Huaso/hueso.

      1. Emi.*

        Oh golly, I have a cousin who went out to buy chair cushions in Germany, but he only knew the word “Kissen,” which means “pillow.” Buuuut he didn’t know it as well as he thought he did, because he went up to the poor saleswoman and asked for “Kuessen,” which means “kisses”—“but not for here [pointing to his cheek], for here [pointing to his bum].”

        1. mrs__peel*

          There’s a whole thing about this in Jerome K. Jerome’s book “Three Men on the Bummel” (where he and his two British pals are touring Germany). It’s hilarious.

      2. Countess Boochie Flagrante*

        Oh god, I feel this.

        In college, I took Japanese and Spanish classes back-to-back. They were on very different levels — I was in 100-level Japanese and then 400-level Spanish — but my brain was very not good at differentiating what word went with what language. (In my defense, there are a lot of crossovers, especially in the two-syllable category. Casa/kasa, taco/tako, etc…)

        Well, in Japanese, if you’re searching for a word, one of the fillers you use is ‘ano.’ It’s the equivalent of ‘um.’

        It also mean things in Spanish. Things you don’t really want to just randomly drop in conversation with your professor about Ibero-Moorish architecture.

        (For those who don’t know, ano means anus in Spanish.)

        1. Todd Chrisley Knows Best*

          I spent most of this post trying to figure out what was so wrong with “year”, so I’m sure my Spanish teacher is sending a death glare at me from miles away since I forgot about the differences in having an accent or not. Language is hard.

    5. doubleblankie*

      too funny. Reminds me of when we had a Chinese delegation visit us, quite a high level one. I speak Chinese but it gets really rusty if it’s been a while.
      And I accidentally starting talking about how they had arrived at Hitler airport instead of Heathrow airport. They were very polite about it and pretended not to notice…

    6. JKP*

      Reminds me of when I was at a fan convention, standing in line waiting for a celebrity autograph. The lady in front of me was Deaf with an interpreter. When it was her turn to get an autograph, the celebrity tried to be gracious and tried to sign probably the only ASL they knew: “Nice to meet you.”

      Except they actually signed “Nice to f*ck you.”

        1. Cherith Ponsonby*

          Check out Adam Hills (Aussie comedian) – I can’t google right now but in one video he explains “F you and F the lot of you”, and in another “F you and the horse you rode in on” :)

          1. JKP*

            Thank you for that. His bit on sign language was hilarious. (Even if American Sign is different than British or Australian sign).

      1. J*

        I have a friend who’s an interpreter and her husband made that mistake when meeting one of her clients! Luckily the client thought it was hilarious.

      2. phyllis b*

        This reminds me of a story I read in Reader’s Digest. A mother was taking a sign language class because her daughter was deaf and the instructor was showing them obscenities that they wouldn’t know. Later she and her daughter were talking and she threw a couple in to see if her daughter would pick them up. Her daughter told her to go wash her hands with soap.

    7. overcaffeinatedandqueer*

      That reminds me of what happened to my poor friend on an exchange trip to Costa Rica!

      Her Spanish was good, but still only high school level, and she did not know slang and connotations. Out for breakfast, asks waiter “Usted tiene huevos?” (Eggs).

      He got an evil grin and replied, “siiii, tengo huevos graaaaandeeess!”

      It turns out that “huevos” also means, um, the thing that male pets lose when you neuter them, and that particular way of asking “do you have” is more meaning do you, personally, have, rather than does your shop have.

      1. Specialk9*

        Yeah, similar thing with saying I’m hot (as in warm) on Spanish. Nowadays I just say that I have heat, because I came remember in the moment which ‘to be’ verb form means hot vs horny.

    8. Corrupted by Coffee*

      When my husband and I started taking Japanese, we had to introduce ourselves to the class. When he stood up and said Hi, my name is —–, the teacher burst out laughing. It took him awhile to regain his composure, at which point he informed the entire class that my husband’s name meant “diarrhea” in Japanese.

    9. Veronica*

      A friend of mine was studying abroad in a Spanish-speaking Latin American country. Apparently the word for “to shower” and the word for “to douche” are very, very similar. Yep, she announced to her whole host family that she was going upstairs to douche.

    10. Middle School Teacher*

      I was living and working in Poland. I spoke barely any Polish. My friends and I were looking for the movie theatre. I said I would ask a hot dog vendor for directions.

      The words for “excuse me” and “I invite you” sound very similar in Polish. So instead of asking politely for directions to the movie theatre, I asked him to come with me. I didn’t live that one down for a while.

    11. Chameleon*

      When I was in college, I had taken one semester of Japanese and had managed to pick up a few words here and there outside of class. A friend was hosting two exchange students from Japan and we were having lunch together. Excited to show off the tiny little bit of the language, I offered one of them a bowl of rice in Japanese, “Meshi wa ikaga desu ka?” They looked at each other very confusedly.

      I hadn’t realized that while “meshi” is a word for “rice” the more proper term for rice you are eating is “gohan”…and I also had lengthened the first vowel, making it “meishi.”

      I had offered them a bowl of rice as my business card.

    12. Bluesboy*

      I once confused the word ‘pompelmo’ and ‘pompino’ in Italian.

      ‘Pompelmo’ means grapefruit. I wanted to ask the nice lady in the market what she charged for grapefruit. Unfortunately I asked what she charged for a pompino. Which means oral sex.

  7. Detective Amy Santiago*

    We had someone on our team give her notice because she was looking for a better work/life balance. It was common for us to throw a going away potluck in those type of circumstances. The day of the potluck, we got her to the conference room on some other pretext and she stood in front of the room awkwardly and told us that she wasn’t actually leaving now because she was going to be moving to a different position with more flexible hours.

    1. Merci Dee*

      That’s when your co-workers just smile and say, “So . . . yay on your new, more-flexible position! Let’s eat this delicious food to celebrate!”

      1. K.*

        I can totally see myself saying “Well … let’s eat!” to break the tension in that situation, and start passing out plates.

  8. Undercover Commenter*

    My manager told our team (a mix of women and gay men) that we were such awesome employees we all deserved vibrators.

      1. Snark*

        I can’t tell whether I hope he meant something else, or whether I will luxuriate in the secondhand awkwardness of knowing he actually meant that. Either way, A++ five stars would cringe again

        1. SusanIvanova*

          Maybe we’ve found the one person who believes those ads that show suspiciously shaped “massage devices” being used for backaches and other body parts.

          1. Working Hypothesis*

            Actually, they do work for some genuine massage purposes. I’ve recommended them to clients who have chronic migraines or tension headaches — only women; I don’t think I could bring myself to recommend going out and buying a vibrator to a man, no matter how bad his headaches were. But I’ve never yet had a female client who didn’t either already own one, or know where to get one easily, so I will occasionally suggest applying one to the painful area of the head, and it usually helps.

  9. Alex*

    On my first day at Old Job, I was running an errand for my director and went to fetch documents from someone else. I left their office and quickly turned around not realizing a large concrete column was there and body slammed into it. I was flushed, flustered and embarrassed and left quickly. I ended have having a hairline fracture on my cheek and it hurt to smile for about 3 weeks afterward. Never told anybody about it!

    1. overcaffeinatedandqueer*

      I was at the Mall of America with my church youth group once, and my friend and I had gone to the Barnes and Noble to pick up a Series of Unfortunate Events book. It had just come out, and being huge fans, we read while walking around with the rest of the group.

      Until I crashed into a pillar. My friend then crashed into ME, because she had been behind me and looking to me to keep us on track. Youth director helped us up while trying not to laugh, and said that one of us should read aloud so the other could look where she was going.

  10. Mayor of Llamatown*

    A new coworker was introducing herself during a web conference. She went into great detail about her son’s relationship with his wife, how they had courted instead of dating, and went into great detail about what that meant in terms of intimate activity. I never found out exactly what others’ reactions were, but I was cringing all over.

    1. paul*

      You win. or I hope you do; I’d hate to see the story that beats this!*

      *that is a lie, I would love to. So long as I’m not involved.

        1. Aurora Leigh*

          They don’t always hold hands. Depends on the couple. Sometimes side hugs, sometimes no touching period.

        2. Time Traveller*

          Back in the 90’s, I endured a two hour lesson on the benefits of avoiding premarital handholding. Chastity was very important to the adults around us.

          The theory is that when you are married, you will know that your spouse will never cheat on you, because you can think back on those days when you still loved each other and how in spite of that you were able to exercise restraint and not hold hands, so you can know for sure that even if your spouse comes to love someone else, they won’t hold hands with them, either. I don’t know why it took two hours to say all that, it wasn’t very complicated.

          I think it’s just a way of trying to find certainty in life where there can be no such thing. People want to think they can know for sure they’ll be safe instead of having to trust, but modesty isn’t some kind of magic spell that will ward off heartbreak.

          1. Working Hypothesis*

            And honestly, if my spouse fell in love with somebody else, whether or not they’d held hands would not be the most urgent issue on my mind.

      1. Daria Grace*

        Courting normally tends to mean intense oversight from parents/other authority figures and little to no physical contact

      2. Mayor of Llamatown*

        Pretty much what everyone said already, but it was explained to us that courting meant no sexual intimacy (yes, in those words) and that after a year he gave her a promise ring, and after another year he proposed.

        I don’t judge how others manage their relationships or what they think is right/moral. I just don’t particularly want to hear about it. Especially about someone else’s son who I’ve never met.

    2. Emi.*

      Whaaaaaat

      I had the opposite problem–one of my coworkers telling me about his son’s romantic woes, which apparently cannot be adequately explained without the line “And that’s how I found out my son wasn’t a virgin anymore.”

    3. Rebecca in Dallas*

      Haha, similar story though not nearly as cringey!

      We had a new employee starting in our department, so a coworker (Arya) and I offered to take her out to lunch. Arya and I didn’t work all that closely together, but I’d been around her enough and she is pretty friendly. Well we’re doing the usual get-to-know-you small talk with our new coworker, coworker asked Arya if she had kids. Arya said she had a daughter that had just gone off to college and then for some reason went into a very long explanation about how she had wanted to have more kids, but her husband didn’t and they gone back and forth for years about whether to have more kids… It was just so personal to go into all this detail to someone that she just met! I was cringing so hard and I could tell our new coworker was just thinking “What have I gotten myself into?!”

  11. MovieMaven*

    While sitting in the corner of a room, prepping for a client meeting, my friend witnessed the owner of the business pace into the room and begin a passionate self motivation ritual [ie. “you can do this sh**, you’re the f***ing best, now get out there and win!”]. And then he left – my friend froze as if he was hiding from a T-rex… thankfully he lived to tell the tale.

    1. EddieSherbert*

      Ohhhh that poor guy. Haha!

      Makes me think of that Friends when Ross is dating the daughter of Rachel’s boyfriend, and ends up hiding under the man’s bed and witnessing his “pump up speech” in the mirror….

      1. Detective Amy Santiago*

        It also happened to Jack on 30 Rock! He accidentally had his mic on and a whole room full of people heard him psyching himself up.

        1. Veronica*

          I was just rewatching the whole run of 30 Rock, and I had to skip that episode. It made me cringe so hard I just couldn’t bear to watch it again.

      2. GetYaGritHeeere*

        I was picturing Dwight Shrute when he was in the stairwell doing karate and hyping himself up. Also, that T-Rex comment just paints the picture so perfectly!

    2. Damn it, Hardison!*

      Or on 30 Rock when Jack was giving himself a pep talk in the bathroom before a leadership speech, but didn’t realize he was already on a live microphone.

    3. JokersandRogues*

      For creepy psych-up, Sexy Beast has a scene with Ben Kingsley’s character screaming at himself in a mirror.

  12. Always Awkward*

    When I was 23 I was promoted into a leadership position. My then boyfriend (now husband) had been on that team for several years. To be upfront I asked my boss if my relationship would cause problems with my new role. He paused and thought a bit before telling me that no, it’s still okay because we don’t supervise the same department or work together in a way that would be impacted by a relationship. He went on to explain that really in this role I could date anyone at the location I wanted to except for him. He and I would just never work. I think he saw me start to laugh at the thought (he’s considerably older and shorter, and less active than I am and I was 23!). Seeing my almost reaction he made a comment about having a very busy dating life anyway. He’s still my boss several years later.

  13. Andy*

    last week I was coming down with flu but I didn’t know it yet
    and a coworker (several rungs up on the ladder) come over to compliment me on something particularly polite I had said moths earlier in an awkward situation.
    It was a very nice compliment.
    Due to my as of the time not yet recognized illness related loopiness I responded to the lovely compliment with the following expletive: Well MuthaFurkER, thank yew.
    So, in response to a very nice compliment on a polite thing I said I washed myself in irony and answered in an exceedingly impolite manner.
    I am still mortified.
    Deeply.

    1. Competent Commenter*

      I oh FEEL you! I’m on day 15 of the illness that’s going around my work (not the flu but really debilitating) and I have been really loopy. Just been observing myself making strange choices, hoping nothing I do causes any long-term problems!

  14. Wannabe Disney Princess*

    I was walking into the office. Had my purse. Lunchbox. Coat. Everything. Unbeknownst to me, someone had spilled some water right in my path. It was like my own personal patch of black ice. I didn’t just slip. Oh, no. That would have been far too dignified. I flew. Not quite like an eagle. More like a drunk pigeon. FACE FIRST. My purse soared to right (still thankful it didn’t injure or kill any passersby) and my lunch went careening to the left. Once I was wheels down, I confirmed that I was uninjured and alive. My pride, however, was desperately hoping the embarrassment would kill me first. I finally gathered myself. Picked up my stuff. And faced the stunned faces of my coworkers as I limped back to my desk.

    1. Reba*

      Watched Olympics women’s downhill skiing. When they wipe out those beautiful valkyries can go a loooong way penguin-style (on their bellies).

        1. LizB*

          Solidarity! I ate it hard in front of my coworkers in the parking lot the other week trying to kick the accumulated snow boogers off my car. My legs went straight out from under me, I shouted “WOOP!” really loudly and landed flat on my back. Then I got the knees of my slacks wet trying to stand up as quickly as possible.

          Then there was the time I had a similar wipeout crossing the street right before the light turned… and the time the sidewalk was only partially covered with ice, but I managed to slip on the icy bit with my left foot and land on the bare concrete with my right knee…I may not be cut out for living somewhere with icy winters, but I persevere.

          1. Penny*

            LizB literally that exact thing happened to me down to the position you fell in (2nd paragraph)! I was on campus crossing a road between sides of the campus & of course people were waiting at the light where i fell. Glad it was dark so i didn’t have to see their laughter. Of course i continued on to watch a movie in class for extra credit, so i only had to sit there through Lord of the freaking Rings in horrible pain. My knee was bruised for months.

        2. Detective Amy Santiago*

          I fell over a construction sign in downtown Chicago.

          I’m pretty short, so I was trying to walk under it. I didn’t realize that the two vertical metal poles holding it up were connected by a horizontal metal bar that was just below my knees. I took a couple steps forward and was like “why can’t I move” and the next thing I knew I was practically upside down.

        3. Nolan*

          In my last year of retail I fell down the stairs at work twice in one month. The first time happened in my home store, my heel got caught as I was going down, right leg folded beneath me, arms extended to the walls, left leg splayed out in front. My left shoe flew off my foot and my smartphone flew out of its holster, both ended up at the bottom of the stairs while I managed to hold myself after a couple feet. When a coworker rushed to the bottom of the stairs to make sure I was okay I exclaimed, “is that my phone!? Is the screen cracked!?”

          The second time was at another store I was attending a training in. It had snowed, and I was wearing wellies. I’d just bought a coffee, took one step down and on the second step my foot shot out from under me and I flew down the remaining 20 or so on my ass. The coffee exploded everywhere. When I got up and went into the conference room, the trainer and other attendees just stared at me like it was nbd, and left me to clean up the mess by myself. That store was only 15 min from my apartment, but I never set foot in it again.

          1. Petunia*

            I slipped coming down the stairs at a conference last fall – just the last couple of stairs – and fell over. The friend walking with me was totally horrified and tried to haul me up but he’s not a large guy and it was a lot of effort partly because I was laughing like a loon.

            He was worried for the whole rest of the conference. It must have been a surprise to see me just go over like that.

        4. overcaffeinatedandqueer*

          I once fell on some glare ice on my way to a college class while clutching a very hot coffee!

          Didn’t even try to save myself. Backpack weight pulled me slooowly down as I skittered and flailed. I had just enough time to decide what to save from impact.

          Fall forward and save laptop and homework? Nope. Fall straight back, no attempt to catch self, with coffee holding hand straight up in the air like an Olympic torch bearer.

          It felt like I broke my back, but I saved the coffee!

          1. Specialk9*

            Laughing so hard at this mental image. I would love you forever just for this. Like, hey, let’s be best friends, coffee saver person.

        5. Adlib*

          Was salting my driveway Sunday after a mild ice storm. Managed to steadily slide down the middle while salting. Later I wiped out while standing almost still. Nobody was out, but I wish my doorbell cam had picked it up!

    2. Nita*

      Ouch! Your description is epic though.

      And that reminds me, my husband flew into his office once! But first, he flew into a truck. His office was in a bit of a windy neighborhood, and one day he comes out of the subway, and a gust of wind just picks him up, and he goes flying through the air right at the truck, Superman-style, with the arm outstretched and all. He’s a big muscular guy, so I wouldn’t have believed it, but he’d called me freaking out that if the wind could pick him up, I should NOT LEAVE THE SUBWAY unless I’m hanging on to something.

      Frankly, a small part of me was disappointed when I got off at my stop and found that the wind in my neighborhood doesn’t pack the same punch… flying sounds kind of awesome even when it ends with a bruise.

      1. Working Hypothesis*

        When I was a kid, the local carnival was held on a weekend which featured a ginornous, and very sudden, windstorm. Everything closed down and we were all sent home when the wind began to pick up. It was only about three blocks to my house, but I flew almost a block of that before I managed to snag hold of a passing lamppost and haul myself back down to the ground!! After that, I kind of crawled along the building line for the last block, terrified that if the wind picked me up again it might not put me down till I was over the river.

        I admit that, once I got hold of that lamppost and could afford to stop being terrified, it *was* pretty cool to have experienced flight, though. I’ve done the indoor skydiving things they have a few times, and it’s actually very similar, so if you want to find out what it’s like, I recommend those.

    3. JB (not in Houston)*

      I have so many stories of my falling down in front of people. Once in law school, I stuck my feet on the rails of the chair, then leaned over to pick up a pen I had dropped. My heels had become stuck on the rails, and so when the chair started to tip over, I couldn’t put my feet down to stop it. I was in the front row. The whole class got to see my chair fall sideway with me sitting in it.

      Another time I had my hands full of books as I was leaving a building, so I decided to use my foot to press the button to automatically open the door. Although I’d done this many times before, I guess because I was wearing boots with heels and had a heavy backpack on, I started to tip backwards. To stop myself from falling, I slammed my foot back down to the ground. All that accomplished, though, was to stick my leg straight into the paper recycling bin next to the door. So I fell straight back, leg in the bin, taking the bin over with me. Fortunately, I guess, the backpack absorbed the fall, so I wasn’t hurt, just really embarrassed.

      1. Legal Beagle*

        The recycling bin is just the perfect cherry on top! I’m a huge klutz, so I sympathize.

        I was sitting in a folding chair at a friend’s dinner party. I dropped my fork, leaned over a bit too far to get it, and the chair slipped out from under me and dumped me onto the floor. I was also 12 weeks pregnant but wasn’t telling anyone yet, so I just silently freaked out for the rest of the party. (It wasn’t a big fall, but I was a nervous first-time pregnant lady.)

      2. Free Meerkats*

        Since this wasn’t at work, I’m asking Alison to pick someone else if the algorithm chooses me.

        This was back in the 70s, a friend had bought a new Honda 450 motorcycle and we were all outside the barracks looking at each others’ bikes. He offered me a ride on it and I swung my leg over and, since it was already running, off I went. What I didn’t notice was that my pant leg had gone over the kick-start lever when I got on.

        Being the (I thought, with the stupidity of youth) suave young man I was, as I rode up to a light that happened to have a car with some attractive females in it sitting there waiting, I decided to be really cool and come to a stop before I put my foot down. So I came to a full stop and went to put my right foot down, only to discover it wasn’t going to move that way.

        You remember the tricycle guy on Laugh In? That was me. Came to a stop and promptly fell over. Needless to say, I didn’t impress the young ladies in the way I intended. And I had to buy a new turn signal for the friend. But of all the injuries, my pride was hurt most of all.

    4. justsomeone*

      Your description of the event is so well done I’m sitting here chuckling audibly to myself, partially because I’ve also slipped in a glorious manner and if I can’t laugh I’ll cry.

  15. Sarah*

    So a woman I worked with was super excited to be pregnant and expected all of us to be equally excited. She decided to throw herself a gender reveal party at the office (presumably after having one for friends and family? This part was unclear) and sent a department-wide email asking us all to meet at 3:00 that day. Now, 3:00 was a bad time for my team specifically as we had daily 3:15 deadlines, and it was pretty common for us to miss the start of birthday/anniversary celebrations each month so we could hit our KPIs. But she came around and did everything but physically lift us out of our seats – she would not start the “meeting” until we were all standing around.
    She then had her friend from another department walk up with a bunch of blue and pink balloons and started popping them one by one until she was left with a blue balloon and she was shouting, “A BOY! I’m having A BOY! Aren’t you so excited? Isn’t that great? A BOY!” Everybody just stood around awkwardly while she talked at them about how excited they must be for her and how proud her husband was.
    By the time this whole charade was over my team had missed their deadlines and screwed up our KPIs for the week. On the plus side, we got to teach everybody about assignable cause variation by highlighting the dip and circling it with a note that said “Surprise gender reveal party”.

    1. Falling Diphthong*

      I have actual children, of all the major genders, and don’t remotely understand gender reveal parties. Unless the context is “We want to eat simple carbohydrates, and this is the second-week-of-February pretext. No, Neal, no one cares whether you are actually pregnant. Just hand out the cupcakes.”

      1. Falling Diphthong*

        Also, the symbolism of popping the balloons is really freaky. Like reproductive Hunger Games.

        1. Rebecca in Dallas*

          This is the part I can’t stop laughing at! Like someone just popping balloons and everyone jumping each time. My coworkers must think I’m a loon.

  16. MsMaryMary*

    I once made an expansive sweeping gesture and smacked one of my direct reports in the face.

    One of my friends was having a one on one with someone she managed, and he told her that he was a little anal retentive when it came to certain parts of his jobs and he was concerned it might cause problems with his coworkers. “Oh, don’t worry,” she said, “I LOVE anal!”

    1. London Calling*

      Oh, have done that but to a total stranger who staggered back in surprise, no doubt wondering why this idiot she’d never met before was socking her in the jaw.

    2. JB (not in Houston)*

      I have (lightly) punched my sister in the face before while putting on a coat, and then again later the same day when trying to show someone how it had happened in the first place.

      1. Mabel*

        I did this once on the subway while taking off my backpack. I accidentally smacked the woman right on the temple and knocked her glasses halfway off her face. I felt terrible, but she was amazingly gracious.

    3. Lily Puddle*

      On two separate occasions I have smacked the person sitting at the table behind me in a restaurant while making an expansive sweeping gesture. But at least it wasn’t someone I worked with, so I didn’t have to see the poor folks I smacked every again.

      1. JaneB*

        I hope nice threw my scarf back over my shoulder and hit the thing behind me. It wasn’t a person. It was a seven foot tall cheese plant, which fell onto our table. How w to attract a lot of attention…

      2. BF*

        My boss was in a meeting where the general made a big gesture and knocked his chewing tobacco spit cup into the lap of the admin assigned to take notes. My boss didn’t know generals could apologize that much! The general gave her the rest of the day and the next day off and he would clear it with her boss. And she was to send him the cleaning bill and if the outfit couldn’t be cleaned to send him the receipts for any replacement items.
        I was impressed she didn’t throw up on him because I find that stuff disgusting.

    4. Lily Rowan*

      This isn’t that embarrassing, but it literally just happened in my last meeting — I was laying out a couple of options and said, “I go both ways.”

      Really, self????

      1. London Calling*

        Sometimes you have to wonder if your brain and your mouth are in a conspiracy to make you look as bad as possible, don’t you?

    5. palomar*

      I was in a departmental meeting once when our CFO said something about being really anal retentive and an older coworker piped up from across the room, “Oh, anal’s great! I love anal!” It’s been at least a decade but every time I think about it I laugh so hard I see spots. Bless her heart.

    6. Alex the Alchemist*

      In my community choir in high school, one of my friends was putting on her robes and accidentally elbowed one of the choir’s littlest members in the face. The kid’s response? “It’s ok, my mom does that all the time.”

  17. Lady By The Lake*

    I interned for a firm where a Very Important Person (think former President or VP of the US) worked. As a treat for the interns, we had a meet and greet with the VIP and he went around and asked us all where we had gone to college. I went to a famously artsy school. When he got to me and I said the name of my college, he said, “Oh, Artsy School. I knew some Artsy School girls. Is everyone still running around the woods naked, or did you do actual work?” It is thirty years later and I am still at a loss as to how to respond to that in front of sixty strangers.

    1. Detective Amy Santiago*

      Even though you said this was 30 years ago, I am choosing to believe it was GWB who said this to you because that mental image is way too funny in my head.

        1. she was a fast machine*

          Same here; I’m picturing Clinton 100% and half the room being utterly swept up in his “charm”

      1. AMPG*

        I went to Wesleyan, and there aren’t any woods nearby, so it couldn’t be. Now, if he had referenced lying on the hillside stoned out of your gourd…. :)

        1. Dee-Nice*

          Eh, there were copses of trees and verdantry around. Maybe “woods” was used loosely. Nudity certainly abounded.

        2. Dylan Is A Lady*

          I went to Wesleyan, too. The graveyard is an excellent spot for shenanigans, but the tree cover is scant.

          Sarah Lawrence, on the other hand…

            1. Lady By The Lake*

              That was the other thing that was really awkward. We DID run around in the woods naked. But I also had an excellent education. The knowledge that what he was saying was true only added to the awkward. Added my email.

              1. Working Hypothesis*

                I spent a summer at Bennington, when I was in high school. Gorgeous place, and we did a lot of running around in the woods, but we were warned explicitly to keep well covered because of poison ivy! I didn’t know that poison ivy only targeted those under 18…

        1. Elemeno P.*

          Oh my god, I went to Bennington too! I was thinking that it sounded like us, but then thought, “Nah, that’s too obscure.”

          We did still run around naked in the woods when I attended.

        2. Elizabeth H.*

          I knew it was Bennington!!! Immediately! I was going to ask “But DID you” then read the rest of the comments :)

    2. Sue Wilson*

      My response: “The workload was intense, but it sounds like you remember Artsy School fondly.”

    3. Anon.*

      Can relate. Went to school that was known for having a “Tent of Consent” and other sexual/hippie events and it somehow seems to always be the first thing people ask about.

  18. EddieSherbert*

    At a previous job, an Assistant Product Manager was giving a presentation to a large group (including their boss’s boss) for some new regulations at one of the job sites (construction), and one of their friends that was out on another job site sent them a Lync message… and you know how the first few words pop up in the corner of their screen? Yeah, it said “sup, my n*****”. Projected on this absolutely huge screen. The APM moved fast, so it was only there a couple seconds, but almost everyone saw it. And the people that didn’t see it were very quickly filled in. And their boss’s boss didn’t say a word, but was literally just red in the face (rage? embarrassment?) glaring daggers.

    Both the APM and their friend were called into HR. They were not fired (whew) and I don’t know what the consequences were.

    1. Sarah*

      Oh man!

      I was hosting a webinar and usually have my Skype set to do not disturb when I’m doing that but it didn’t work this last time, so my COO and the director of our billing team saw a message from a coworker pop up that just said, “So, I’m f***ed.”

      1. Arjay*

        Yes, do not disturb is a necessary precaution. I have a friend here who is in a lot of meetings and one day I had a lot to vent about it. I started it off with “Are you alone?” :)

        1. EddieSherbert*

          For non-work related stuff, I always send “hey!” on its own… and then my actual message in a second message. So only the “hey” pops up. Just in case.

          …. and I literally do that because of what happened in this meeting! Haha

    2. Damn it, Hardison!*

      I am so happy that Skype doesn’t have that problem. I’ve seen a few embarrassing things pop up in the past, usually along the lines of “WTF, X is an idiot.”

    3. Rebecca in Dallas*

      Once I sent my husband a g-chat message. “Are your coworkers still being super annoying?” You guessed it, he had his computer projected to show them something.

    4. ChrysantheMumsTheWord*

      This reminds me of when I was remotely making a very important presentation.

      I was in our office with several high level execs, the owner, VP and director were on-site with the prospective client and we were connected via webcam, etc.

      During my part of the software demo I mis-typed the word SHIP which was projected on the wall in both locations. I kept talking while seeing the looks of horror at the client site, while I tried to quickly fix my error. Unfortunately, on my end the person sitting next to me loudly gasped and then laugh-shouted “HA!” before dramatically clamping their hand over their mouth.

      I was mortified and those that were at the client site never spoke a word of my gaff when they returned which just made it worse. We didn’t get the client but I have no idea if it had anything to do with me.

    5. zora*

      I was not projecting, and this was more a “Huge Work Mistake Do Not Do” than an ‘Awkward Moment’, but I was at BEC mode with a coworker, while she really thought we were BFFs. She was IMing me all kinds of things that were the exact reason I was so frustrated with her, and I switched to another IM window and sent a whole long rant about exactly why Circe was “such a jerk and it’s driving me crazy!!!”…. Yup, I hadn’t switched windows…………….

      It was super bad, and she was so angry at me, and we had to have lots of “Talks” about my feelings for many many weeks. I felt really bad for hurting her feelings, but honestly, she was causing me lots of work related problems. But from then on I am SUPER careful about ever putting vents about people in writing EVER.

  19. LibraryGnome*

    I was 19 years old and working as the manager of a spa. Part of the massage therapist interview process is giving the management team a massage to demonstrate their techniques. This super buff, blond, surfer-dude type is practicing on me and I ask for my glutes to be worked on, as they are a problem area for me. He proceeds to take the sheet, pull it back to fully expose one cheek, and uses his hand to wedge it down my crack. Needless to say, that is not a normal draping technique and clients would have definitely came to me over that… We hired him, but he got a lot of draping training before he was allowed to work on clients. Definitely the most awkward day of work ever.

    1. Working Hypothesis*

      Oh good grief. I’m a massage therapist and I am absolutely cringing in professional mortification for that guy!

      If I were dealing with someone who wasn’t a regular client — especially in a job trial — I would work glutes through the sheet and not undrape at all. With a regular, if there were actual reason (there usually isn’t), I might fold the sheet back so part of one cheek were exposed, but you fold, not wedge!

  20. CatCat*

    Oh man, this book sounds amazing. I already feel secondhand embarrassment for the deliciously awkward tales that must be contained inside. I want to read it and I don’t! (But I will!)

    Awkward work situation: I had a boss who had surgically implanted her foot into her mouth. In one memorable moment, a staff member on the team shared that her son and daughter-in-law were expecting their second child (and her second grandchild) so she was thrilled. Boss: “Haven’t they heard of birth control?” Oooooooh… sooo much pained looks around the room. None of us could believe she just said that.

    1. Detective Amy Santiago*

      This just reminded me of the time when our manager was diagnosed with breast cancer and pulled us into a meeting to tell us. One of my coworkers blurted out “are you going to have to get your boobs cut off”.

      She got called into HR that afternoon.

      1. Countess Boochie Flagrante*

        Oh my god, that sounds like my mother. Not work related so I’m not sharing the gruesome stories, but she’s very prone to saying the first thing that comes to mind and it’s painful.

    2. Amy Farrah Fowler*

      Omg… My dad is the worst about stuff like that. Not in a work situation, but pretty much every time someone announces a pregnancy, he says “don’t they know what causes that?”

      “Yes, dad. Everyone knows what causes that.”

  21. Boy oh boy*

    My boss got a haircut I thought was incredibly unflattering . It was a mullet with lots of spiky layering that made his small, angular face look almost rat-like. (This was in 2008-ish and mullets were pretty much a reviled joke by then, so he couldn’t even use ‘it’s on-trend!’ as an excuse.)

    I saw him and could not control my look of horror. It was obvious that I thought it was terrible, he was clearly offended, and I couldn’t look at him properly for the rest of the week… he even ‘joked’ that I didn’t like it in a meeting but he was not happy. I have rarely felt so awkward/ashamed…

    1. ChrysantheMumsTheWord*

      I had a former supervisor see my new haircut and reply, “Did you do that on purpose?”

      1. Blondie*

        Once I thought I would try a new hair color (one that was supposed to wash out in 6-12 shampoos). It was light golden brown. I was golden blonde. The resulting color was auburn. Let me tell you, it did not wash out in 6-12 shampoos. (And the color never completely washed out. The result, though, was a nice ash blonde.) When I walked into work, one of my managers asked me “What did you do to your head?”

        1. Yikes!*

          My colleague came to work one day with a tight perm (it was the early ’90s), and a second colleague saw her, and blurted “Lisa, what did you do? You have to go right back to the salon and DEMAND your money back!”

  22. Casuan*

    At ThemePark, an older man asked me something & I laughed because he was mimicking one of the Characters. Then I realised that he had a voice-box & that was his voice. And then my horror grew when I saw the number tattoo on his forearm because this man had been through traumatising events & by laughing I wasn’t doing my job at the Happiest Place on Earth.
    Thankfully he was gracious about it!!

      1. Casuan*

        ummm… Thanks?
        30 years later & I still can’t forget this man. The snapshot of that moment is permanently seared in my head.
        Actually I’m quite grateful to this gentleman because after all of about two minutes this encounter helped me to become more aware of others & not so quick to jump to conclusions.

  23. Who the eff is Hank?*

    My first job out of college was in an office where almost all the walls were made of glass. I was walking into a conference room for a meeting but instead of going through the doorway I accidentally slammed into one of the very shiny and undetectable glass panel walls. The sound was magnificent as the glass cracked all the way down the panel from where I’d hit my head. Also, this was an all-hands meeting, so literally every person in the office saw this happen.

    1. Who the eff is Hank?*

      Replying to include my email in the comment for Alison’s drawing. But I’ll give everyone a bonus embarrassing story to make the comment worth it.

      My current job is at a nonprofit that works with children. My boss sometimes brings in doughnuts for the kids in the morning and gives anything leftover to the staff. Last week I went into his office to give him something and saw an empty doughnut box on his desk. In feigned disappointment I said, “What, none for us?!” but he thought I was being serious. He had such a sad look on his face and apologized for not bringing us doughnuts and then I had to apologize and explain I was kidding. I felt so bad for making him feel bad.

    2. Ruth ok*

      There are couple of shops that clearly have this problem regularly and have actually stuck signs on the doors to warn people. I don’t know why they can’t just add a few frosted stripes or something.

      1. hermit crab*

        We recently had some of those little frosted stripes installed in our office, because people were walking into doors. They’re apparently called “distraction marks”!

      2. zora*

        Our office is all glass walls and doors, part of the design is big red dots on every panel of glass, one at eye level and one at knee level. So, you can tell when doors are open.

        That said, I have still bumped into the glass once, but it wasn’t hard enough to break the glass, thank goodness!!!

    3. Reba*

      You know how they have those decals to try to prevent birds from crashing into windows? The one’s I’ve seen are most often bird shaped. What would be the decal shape for clumsy humans?

      1. beanie beans*

        I’m picturing how in cartoons the human cutout of people are so distinct when they run through a wall. :)

  24. Alison Read*

    I owned a produce business – sampling was encouraged. I was talking to a husband and wife and handed her a double cherry, she ate both and I told the husband (because I’d already grabbed one for myself), “Here, you can have my cherry.”

    1. LAI*

      Ok this one isn’t work related but I had to share: in college, my boyfriend and I were attending a football game and had gone to get snacks. I bought nachos that came in a little cardboard box. He got a hot dog. As we were meeting up with all of our friends, I noticed that he had his hands full and said “do you want to put your hot dog in my box?”

      1. SocialMonster*

        My first day on a new job in a bar, I was being trained by the owner. He offered me a piece of bubble gum. I declined by saying “no thanks, I swallow”. His reply was “I think you are going to fit right in here”

  25. bluelyon*

    I , as a customer in this scenario and being slow on the uptake, made a comment about not recognizing the cashier with her clothes on…….

    She was a lifeguard at the pool I swam at – I had only ever seen her in a swimsuit.

      1. bluelyon*

        Conveniently I was a 14 year old girl….she was not much older and 15 years later we remain friends

    1. Original LG*

      I was a lifeguard in college. I guarded the senior swim hour, where everyone over a certain age could swim for free. I ran into one of my regulars at my parents church and he exclaims, “Boy, Original LG, you sure look different with clothes on!” In front of my dad…and the pastor!

    2. Veronica*

      A secondhand story, about a friend of a friend who usually wore a Scottish kilt as part of his ordinary clothing. One day he decided to wear trousers, and a co-worker announced “Bob! I didn’t recognize you with trousers on!”

    3. Clewgarnet*

      I used to live in an old-ish (early 1800s) house that had been (badly) converted into four flats. One of the flats was occupied by some serious stoners, who never thought to block their smoke detector before lighting up at 2am. The smoke alarm was one that automatically called the fire brigade, who then had to go through the entire building to confirm there was no fire. I regularly opened the door to them in my nightwear.

      One day, I was walking down the street and the firefighter who usually came to my flat was collecting money for charity.

      Of course, with a huge grin, he said, “I didn’t recognise you with your clothes on.”

  26. paul*

    Went to work feeling OK; worked a few hours, took lunch. Ate lunch at a sandwich shop.

    About an hour after getting back I was feeling *awful*.

    Went to ask my boss if I could go home and threw up all over her office while asking.

    1. Future Analyst*

      Oh God. This is one of my worst nightmares. I can barely handle vomit, but the thought of vomiting near colleagues makes me ill.

    2. Coalea*

      This is not work-related, but your story reminded me of a time when I was in elementary school and feeling unwell. For whatever reason the nurse wasn’t there that day, so the principal let me lie down on the floor of her office with her blazer tucked under my head as a pillow. Needless to say, I vomited all over it. Also, she was a nun, which somehow made me feel even more awkward.

      1. MsMaryMary*

        My mom taught first grade for many years. On the very first day of school she told the kids that they didn’t need to ask to go to the bathroom if they felt sick, they should just go. She still routinely had sick children come up to her and say, “Mrs M, I don’t feel so [vomit]”

        1. Rebecca in Dallas*

          In fourth grade, I asked our PE coach if I could go to the nurse’s office because I wasn’t feeling well. She thought I just wanted to get out of running laps, so she told me no. Guess who puked all over the gym floor?

          1. Elizabeth West*

            I was in time-out in the library in fifth grade (don’t ask–my teacher was abusive) and felt really bad. I asked the equally awful librarian if I could go to the restroom, but she said no, you’re in time-out, stay put. So I sat there, feeling sicker and sicker. A moment came where I knew everything was going to come up and I lunged out of my chair, ran into the hall, and promptly chundered all over the place. We were right outside my classroom and I heard one of the boys say “Splat!” I turned around and did it again, leaving two huge puddles on the floor.

            They called my mum and I went home for the rest of the week. I kind of wish I’d upchucked ON the librarian.

    3. Partly Cloudy*

      My vomit story is so bad I try never to think about it. Out of town conference with my boss, I accidentally got really drunk and my boss and the bigwig vendor we were hanging out with had to help me back to my hotel room and essentially put me to bed. After helping me throw up in the trash can. Several times. I’m leaving out a lot of details both for anonymity and because it still makes me extremely cringe-y to relive this memory.

    4. overcaffeinatedandqueer*

      High school bio. I had started my period and it was really painful and heavy. I wasn’t bleeding through clothes, but I felt like absolute shit.

      Raised my hand and said, “Excuse me, Mr. S, can I-” CRACK. Fainted across my lab stool.

      1. Windchime*

        This happened to me at work when I was a teenager. I had fainting spells due to severe anemia. I thought I was better so I went to work at the dime store. One minute I was behind the counter; next thing I knew, I was sitting on the floor and my customer had come around to my side and was on the phone with the owner (his number was posted by the phone). It was really embarrassing; the boss had to come and spell me and my mom had to come pick me up.

    5. Lefty*

      Oh, paul… same here.

      Except that I vomited directly onto the shoes of my boss when he kindly tried to open the door for me… the man was wonderful. I apologized and tried to grab some paper towels- he reminded me that he had 6 kids at home and had been through worse. I was mortified, but he was so kind, it made a huge difference in the way I saw him after that!

    6. Escapee from Corporate Management*

      This immediately reminded me of…

      Flounder: “I can’t believe I threw up in front of Dean Wormer.”
      Pinto: “Face it, Kent. You threw up ON Dean Wormer.”

    7. Former Border's Refugee*

      My very first day at my very first job (at a movie theater), I was so anxious I didn’t eat all day. I keeled over from low blood sugar while taking tickets, much to the movie going public’s dismay.

  27. Mickie D*

    I am usually the awkward one so saying I witnessed it is not really accurate. My current job – which I have now been at for almost 5 years – had a bad start. I had worked at a dream job and the owner decided to close. As a result, I found this job. And I cried for my entire first week as I was SURE I had just tanked my career for the rest of my life. I told everyone – unconvincingly that I had allergies – but I was crying all week. They were not sure I was coming back on Monday it was so bad. But I did and 5 years later – love it here. Awkwardness happens.

  28. Js*

    During our board meetings one year, my boss (who has been single for as long as I’ve worked for her) was chatting with a group of co-workers in a lobby. One of the the co-workers says to her, out of the blue, “I haven’t seen you in a while, are you pregnant? When are you due?” To which my boss loudly replied “Nope, not pregnant, just FAT.” Cue horrified looks from everyone else as they go silent and start to back away and scatter. The inquiring person looked like they wanted to die, and after sputtering a few apologies also fled the scene.

    1. Accidental Analyst*

      I had something along the same lines. I’d just finished a training session for new contractors. On of them came up to me and asked if I was pregnant. I said no. She insisted. I said I was bloated. She insisted again. Told her nope just ate something I shouldn’t have. Now wish I had of said yes it’s a gas baby

      1. Elizabeth the Ginger*

        WTF. Bad enough to ask a first time. But it’s about a hundred times as rude to double down and insist. What possible good outcome could insistent-lady be imagining? “Oh my gosh, person I just met, you must be right! How wonderful! Thanks for helping me find out I’m going to be a mother!”

      1. ggg*

        I WAS pregnant. 8.5 months. Someone thought it was useful to tell me, “A couple people were wondering how you got so fat. But don’t worry, I told them you were pregnant.”

        1. LSP*

          That’s a pretty risky thing to say to someone 8.5 months pregnant. You’re liable to set off a crying jag or trigger Hulk-level pregnancy rage.

    2. Partly Cloudy*

      Co-worker 1 had been pregnant and was also overweight (both pre- and post-pregnancy). Co-worker 2 asked her “when are you due again?” Co-worker 1 replied “I had her three months ago.” I was standing right there and it was so awful to watch.

      1. Rebecca in Dallas*

        Similar thing happened to my dad. He asked my mom’s coworker, “When are you due?” “Eighteen months ago.” Ouch! Almost three decades later, he will not assume a woman is pregnant unless she is in active labor. And even then, he’d probably still not ask.

      2. Witty Nickname*

        I had someone do this to me 4 months after my first was born. A few years later, when I was very obviously pregnant with my second, she asked me the same question as we were walking past each other in a hallway. And I acted like I had no idea what she was talking about and just kept walking.

        (I mean, I was really really obviously pregnant and not just overweight. And when I had random strangers stop me in the grocery store to ask when I was due and then act really surprised that 1) it was still 2 months away, not the next day, 2) no, I wasn’t having twins, and 3) and no the baby is not a big boy but a girl who is measuring right on track, I didn’t really mind because I knew it was obvious. But that woman really irritated me. Heh)

      3. Little Orange Nail*

        I have triplets. It destroyed my figure, so even though I am back to my pre-pregnancy weight, my belly is still kind of pregnant-shaped, and probably always will be. I have on several occasions had someone see me with my kids and say something like, “Triplets?! and one more on the way?”

    3. strawberries and raspberries*

      I did this to someone once. (Told them I was just fat, that is.) That was my wake-up call to change my diet.

    4. MsMaryMary*

      When I was 17, I asked a customer when her baby was due. She was not pregnant. In my defense, she was buying a onesie.

      So at least I learned that lesson at 17.

    5. Rebecca in Dallas*

      A coworker and I were in our break room chatting while we got coffee. She was wearing an empire-waist dress and telling me about a baby shower she had hosted over the weekend. This poor guy comes up, hears her talking about the baby shower and says, “Oh, congratulations! When are you due?” Soooooo awkward! I kept assuring her he’d only asked because of the baby shower talk, but she was still really upset about it. :(

    6. Lissa*

      lol, I know I’m not supposed to have sympathy for the asker in these situations because it’s a rude thing to ask, but as someone with a bad brain to mouth filter I always feel so embarrassed/bad for both people.

    7. Elim Garak*

      This happened to my aunt in the elevator at a hospital maternity ward. She never comments but thought that’d be the one safe place to do so. It turned out the woman had an abdominal tumor and she was visiting her sister who just had a baby.

      It is never safe.

    8. Ermintrude Mulholland*

      I love your boss.
      This happened to me a few days ago, probably making me the subject of someone else’s Most Awkward work story. I was in a shop buying a scarf and was cheerfully asked by the cashier when my baby was due. I loudly said “Oh no, I’m not pregnant, that’s just the result of eating too much food”.
      Whilst I feel I dealt with it quite well, and admittedly had just eaten a very large breakfast, it still stang and even more so given that I was standing about 3 feet away from my husband and our Three Month Old Baby

  29. Crystal*

    Several years ago, I worked on the overnight stock team at a national retail store and we had only started carrying groceries a couple months earlier, so we weren’t that used to putting things away yet, and it came on a different truck. One morning, the store was about to open so the entire time was scrambling to stock the freezers on the floor. I was reaching in for a box and one of my co-workers was attempting to get the attention of our team lead, and called his name several times. He was low to the ground and I thought it was strange that he was pretending to not have any legs while doing this, so I stupidly said, “Hey Jason – a legless employee is trying to get your attention.” Jason looks at me with wide eyes and says, “I can’t believe you just said that!” I was confused, until I looked down as the employee came into better view and I saw that he literally had no legs.

    He was an amputee.

    I was mortified and apologized profusely, but he laughed it off. Eventually we became friends and I met his girlfriend, who referred me to the job that I’ve now been at for over a decade.

    1. Thursday Next*

      Some comments are sooooo out there they can circle back to innocence…it was obviously clear you were not trying to be a jerk!

  30. Lore*

    We publish a lot of romance novels at my job, many of them shading into the erotic. I (straight woman) was once having a conversation with my direct supervisor (straight man), in his office, about the new season list, which included our first male/male historical romance. Then our department head (gay man) came by and stood in/unintentionally blocked the door while the conversation gradually shifted into other works of contemporary fiction featuring male/male romances. And sexual partnerships. And explicit sex scenes. And menage sex scenes. And yet somehow none of us could steer the conversation back to safer waters, and Dept Head kept blocking the door, and this went on for like ten excruciating minutes.

    1. Lore*

      Oh, and here’s another one:
      I’m a long-term temp who occupies a teeny tiny office. My colleague, also a temp, comes in to tell me some piece of scandalous work gossip before a meeting and slams the door dramatically to do so. We then try to leave for said meeting with our mutual boss…and the door won’t open. We have to call the boss and ask her to come let us out of my office. Which, btw, is teeny enough to be uncomfortable with two people locked in it because most of the floor space is needed to swing open the door.

      Then she can’t open the door from the outside either. She calls security with their master keys, thinking we’ve somehow accidentally locked it and the lock is jammed. They can’t get it either. She ends up having to get a locksmith to take the handle assembly off the door entirely from the outside.

      It took about an hour and a half. Fortunately the boss thought it was hysterical, and my friendship with the coworker survived a period of basically sitting in each other’s lap on my desk chair because we were expecting the door to fly open at any moment.

        1. Elim Garak*

          Honestly if I were a sitcom writer I’d be mining this thread for gold. You could fill a few seasons with these stories.

      1. Adlib*

        I got locked in a conference room during my last business trip. The corporate office had just switched floors due to remodeling so everyone was still learning the quirks of the new floor. The conference rooms had giant doors that were motorized and closed in from both sides. My team member and I had been working facing away from the doors with them open. My coworker got up to use the restroom or something, and it was taking her a while to come back. Then I heard a knock. Turns out the doors had closed on their own when she left, and I didn’t notice. She thought I had closed them for a call or something. She went to get maintenance, and they locked the doors open. I need to ask her if they finally fixed them!

        1. Itsa Me*

          I didn’t witness this, but we had a client visitor at a site location not in the US. They have security badge readers to open doors going both in and out. If you don’t swipe on your way in, the badge reader won’t let you out. The visitor had not swiped his badge entering a training room, and everyone else in the room left but he stayed behind because he needed to make some phone calls. He was trapped in the room until someone came back to let him out! I suspect this couldn’t happen in the US because of fire codes, but it was crazy!

  31. TotesMaGoats*

    Big event at work with big wigs from our city police department. Kicking off a major partnerships. Lots of money involved. President of my university was there. Everything looks great. My boss walks around the corner to say good morning and….

    Same exact suit-seriously
    Same hairstyle (french twist)
    Same jewelry (black pearl dangle earrings)
    Same shoes

    We just stare at each other because it doesn’t help that we are both the same height and hair color and body type. Then we laughed and resolved to always check our closets before big events but that wasn’t the only matching outfit we had. Did I mention there were pictures to be taken in all our twinning glory?

  32. sparty07*

    After a few margaritas at a welcome dinner, I said one of our VP’s was the CEO’s whipping boy. Meant to say it along the lines of when the CEO needed an answer, he turned to this VP even if it wasn’t in his official responsibility/wheelhouse.

  33. Rincat*

    I don’t really have a single, grand awkward moment, but I used to work for a boss who was so much like Michael Scott, it almost made me cry sometimes. Some awkward moments:

    – When I was pregnant the first time, he asked me how I was doing/feeling as I was heading towards the bathroom. He then realized where I was going and said something like, “Oh go pee! That’s fine! Not that you need my permission!…I mean I’m not interested in that!…I mean…” and kept backpedaling (while I needed to pee really badly!). This was in front of a big group of coworkers.
    – He plugged his daddy blog often, sometimes in meetings with clients and execs.
    – Once he was carrying around a pink travel mug and desperately wanted people to notice it – he would stand in someone’s door and clear his throat and take a big, obvious sip. When we didn’t ask him about it, he said, “Oh, this pink mug? It’s my wife’s, ha ha! No other clean mugs today. Not that I’m too insecure in my manhood to use a pink mug.” My coworker and I were like….wtf? Who cares?

  34. NoMoreMrFixit*

    I have a couple of embarrassing stories from my days working tech support in higher education.

    1. Had a helldesk ticket to look into a problem for a user who wasn’t returning my calls for more info. After a few months I left him a polite message that since I had yet to hear back I was closing his ticket. The next day I walked in to see his black draped photo in the main lobby. Seem he had been on the waiting list for a transplant and died before a donor could be found.

    2. Walked into a classroom later in the day to discover a pair of students passionately getting it on in the middle of the room. I stepped back, closed the door and marched back to my office. Managed to keep a straight face until I sat down at my desk, at which point I cracked up laughing. Best part was a couple of my coworkers were taking a night school class in that same room! I suggested they sit closer to the window than the door.

      1. NoMoreMrFixit*

        force of habit. Been calling it that so long I automatically type that instead of helpdesk. I could probably write books on why they deserved that nickname but better to leave those memories suppressed! :-P

  35. ZSD*

    I would love to win this book!

    I wish this were a funny story, but it’s really just simply awkward: back when I was president of my grad department’s student organization, we were in the middle of having elections for the next year’s leadership when a student from another culture just went on way too long (by American standards) in talking about a problem she had with a professor and asking the candidates how they would help her. What she was doing was probably fine in her culture, but from an American point of view, it just wasn’t something to be brought up in that context, and we were all looking at each other wondering how to bring the meeting back on track without offending her. Unfortunately, I as president completely failed to step up, and eventually another student stepped in and suggested we table the discussion.

  36. Namast'ay in Bed*

    A coworker of mine was heating up a microwave meal and walked away while it was cooking since she could hear the ding from her desk (small office with a kitchenette). Well apparently she accidentally hit an extra zero on the time (think 50:00 minutes instead of 5:00) and after a while smoke ended up pouring out into the entire office. We all had to evacuate while the fire department showed up, but the real kicker was that our office was attached to a hotel and the entire hotel had to evacuate as well.

    We were all laughing about the absurdity of it all, but my poor coworker was dying a thousand deaths as we heard all of the hotel guests complaining and speculating, and then laughing as the firemen carried out the smoldering microwave.

    1. Rebecca in Dallas*

      That exact thing happened to me once! Luckily no hotel needed to be evacuated, but yeah, not my proudest moment.

      1. Cherith Ponsonby*

        That happened to a coworker of mine too, complete with clouds of smoke emanating from the kitchen and one of the fire wardens standing in the doorway making sure no stickybeaks got in. The evacuation tone never actually sounded, so all of us had to sit at our desks attempting to work while the alert tone just kept going and going. After a while we all decided it was close enough to lunchtime that we could just head out.

        As far as I’m aware the culprit never fessed up. (No, it wasn’t me.) But one of the microwaves and both of the toasters were gone by Monday.

      2. Alex the Alchemist*

        Similar thing happened to a friend of mine- She was making Easy Mac in the school lunchroom microwave. Unfortunately, she forgot to add the water before she hit “start.” No evacuation involved, except for the smoking microwave.

      3. Melody Gloucester Pegasus*

        Ha! I did something similar with a combination printer/copier/fax machine at my last job–punched in a fax number when the machine was still set to copier. Fortunately I realized my mistake before anyone came in and demanded to know why I was making like 555,654,321 copies of some inane piece of paperwork.

  37. Arts Marketer*

    For fans of awkwardness I must recommend the podcast Motified! Adults reading their childhood diaries/poetry/writing in front of an audience. It’s endearing and cringy and glorious!

    1. Nines*

      Good call! I adore Mortified! It really is brilliant! The live show is also ridiculously good if you ever get a chance to go!!

  38. Anony*

    My most embarrassing work story was from when I first developed epilepsy. We had a very shaky old projector that would sometimes strobe. I had a seizure in front of everyone and afterwards I cried. I wasn’t embarrassed by the seizure but by the crying.

  39. Saturnalia*

    Oh, just that time I was trying to walk past a group of men on the open stairs, and one of them turns around and gropes the hell out of my breast. I’m choosing to remember it as accidental but the lingering awkwardness (+feeling violated) ruined my day.

      1. Annie Mouse*

        I watched someone discussing that with the female politician involved (yes, it was Jeremy Corbyn’s awkward hi-five attempt!). She was asked if he really did hit her in the chest and her response was along the lines of ‘do you think that would have been my reaction if he had?’ Apparently it was the camera angle and he never actually made contact.

  40. DaisyC*

    I once asked my new grandboss (a guy in his late 50s) if the newly displayed, framed portrait of a baby girl on his desk was his granddaughter. His face deadpan, he said, “That’s my daughter”. Why oh why did I say that?!?! Arrghhhh. Nerves.

  41. Sabine the Very Mean*

    I wish I could revel in my awkwardness and others’ awkwardness but I am genuinely mortified by my own awkwardness and watching others be awkward. Does anyone else feel this way? Does anyone else relate to feeling so embarrassed that you can barely sit through an episode of I Love Lucy? Someone tell me what that is about!

    1. Countess Boochie Flagrante*

      Oh man, you are not alone! I’ve usually heard this referred to as “embarrassment squick” — but watching someone be awkward, even fictionally, practically nauseates me!

      1. fposte*

        Yes! I’m sure there are sociological reasons for it, but it kind of fascinates me as a phenomenon. It’s also funny that if it’s strangers, an awkwardness seems to make them want to talk more to each other even if it’s not about that–suddenly everybody’s keen to share their opinion on the weather or something.

        1. College Career Counselor*

          Fremdschamen! 2nd hand/vicarious embarrassment. One of the reasons that I find it difficult to watch Seinfeld or Curb Your Enthusiasm, or “There’s Something About Mary.” (I walked out of that one) You see the mistake happen, and the rest of the episode/movie is just a cringe-fest.

          1. SarahKay*

            I’ve always avoided “There’s Something About Mary” due to my suspicions that I would find it too embarrassing – clearly I was correct to do so!
            Fawlty Towers is my huge squick; I loved it so much as a kid, but by the time I was 15 or so I just found it unwatchable because of the awfulness of watching Basil Fawlty head deeper and deeper into the most cringe-worthy situations.

    2. Amber Rose*

      Secondhand embarrassment. I suffer it acutely. I’ve been known to leave the room during shows for this reason, and I have on occasion covered my eyes while reading.

      1. JB (not in Houston)*

        Oh, yeah, I do a lot of fastforwarding because I just can’t handle it at all.

        It happens sometimes when I’m in court when another lawyer is flailing in front of a judge. I just have to look down and take furious notes on something else (like a grocery list) so that I don’t have to pay attention.

      2. Merci Dee*

        I absolutely love the movie “Dirty Dancing”, but I absolutely cannot watch during the scene when Baby carries the watermelon into the staff party, and then Johnny’s trying to teach her how to dance. The squatting back-and-forth that she attempts at first is just painful to behold.

      3. JeanB in NC*

        I don’t really feel secondhand embarrassment when reading, but boy do I ever feel it with TV or movies! I can’t watch I Love Lucy at all – same with My Crazy Ex-Girlfriend. I really tried to watch it, but I didn’t make it through the second episode.

        1. Amber Rose*

          I mostly get it with reading comics, tbh. Although a well written novel causes it too sometimes. And it’s silly because I’ll be sitting there, hands over my face, reading through my fingers and feeling awful when realistically I could just… not read that bit. xD

        2. Elizabeth H.*

          I started watching My Crazy Ex-Girlfriend and I really like it, but it is hard to watch because it’s me. It’s way too much ME. It honestly seems plausible to me that I might move across the country to “accidentally” be neighbors with the guy who got away.

          I actually almost did this in that I had been casually dating someone long distance for about nine months, and had been thinking about trying to move there, so I was constantly looking for jobs in my field and in the habit of browsing job postings. Then he met someone local and broke it off. I was idly looking at the job postings in his city out of habit, a pretty cool job came up and after much internal debate I decided to apply to it anyway.

          I ended up getting a phone interview and an in person interview where I flew down there for it. I agonized over whether to tell him about it or not but didn’t. I know I was SUPPOSED to run into him in a mortifying way . . . but unfortunately for story telling purposes, didn’t. (I didn’t take the job because of salary mismatch – but might have otherwise) I had a fantastic time there anyway and all turned out really well. But I still find My Crazy Ex Girlfriend hits WAY too close to home!

      4. eternal teapot*

        SAME. I will watch or read any kind of actual torture or gore, but the second a character sticks their foot in their mouth, I’m out.

    3. Snark*

      My own awkwardness fills me with the urge to crawl in a tiny hole and never emerge. Other people’s is fascinating and delightful – not in a “I shall laugh at your pathetic social skills” way, but in a sympathetic, “oh, I cannot look away, I am cringing in sympathy my poor fellow traveler” sort of way.

      1. fposte*

        Though when I read the ones on here today, there’s an interesting division between ones that give me secondhand cringe and ones that don’t. I totally get why the latter would be embarrassing in the moment, but they’re mostly so mild and so harmless in the larger world that they don’t feel like a humiliation.

        1. Ex-Academic, Future Accountant*

          Mine are very individualized. I love Seinfeld and Curb Your Enthusiasm, but can’t stand bad singing (of any kind — I currently have a neighbor who’s always singing to herself, in an apartment building with very thin walls, and I have to blast something on my headphones to stop myself from being able to hear it). I can’t watch I Claudius or anything else involving speech impediments, because it hits too close to home vis-a-vis problems I myself have. (I read the book in a state of low-grade cringe, and appreciated it, but could not get through the first episode of the TV series at all.)

          I even got called out on my secondhand embarrassment once. Back when I was a PhD student, I was at a conference presenting a paper. My advisor, “Peter”, wasn’t there, and I didn’t know anyone else at the conference (it was a very small conference), so at one of the receptions, I was awkwardly standing around with a bunch of people, including one famous scholar I’d never met before, “John”. He turned out to be the type of guy who “gives people a hard time” as a form of humor.

          I’d introduced myself to these people as a student of Peter’s — he was well known to many of them (smallish field). Someone told a story about being at a conference with Peter many years ago, which involved some confusion because Peter had a backpack that looked identical to someone else’s. Then someone else told a story about *losing* his backpack, at a different conference. So John said “Maybe Peter stole your backpack,” calling back to the first story. And then he and this other guy started riffing on it, coming up with some crazy hypothetical story about Peter stealing the backpack and doing various things.

          For some strange reason, my face is apparently very red by this point. So John, noticing this, says to me: “Why are YOU embarrassed? We’re making fun of HIM, not you.” Well, that didn’t make things any better…

          And that’s how I came to like John Doe, author of Famous Papers X and Y, a whole lot less after meeting him in person.

    4. The Ginger Ginger*

      I can’t watch all the TV talent shows for this very reason. American Idol? Nope! Waaaaaay too much second hand embarrassment. And if I start second hand cringing at any other kind of show? I am off the couch like I’ve been shot out of a cannon. I cannot handle second hand awkwardness in visual media format. Reading it here? Yeah, I can laugh (or skim), but I can’t sit through a tv show or movie like that. *shudder*

    5. Interviewer*

      I can’t watch Ben Stiller movies, because that guy loves to be embarrassed, and I can’t stand to watch it happen.

    6. Anonymeece*

      Yup! I have the same problem. Anytime a second-hand embarrassment scene comes up, I close my eyes and cover my ears. I found out years later that my dad and brother do the same thing! I’ve never been able to sit through: I Love Lucy, Will Ferrell movies, or a bunch of other popular entertainment.

      Interestingly, I’ve read that this is actually a sign of empathy, and not only that, but when people who do this are seeing something embarrassing, it registers in your brain the same way physical pain would.

      So it’s not a bad thing! It just means that you feel someone else’s embarrassment more acutely than others might.

      1. JeanB in NC*

        That’s interesting about the brain thing! I will mute the TV when there is secondhand embarrassment – it doesn’t seem to bother me to watch it if I don’t have to hear it.

        1. hermit crab*

          Ha, I’m the same way. I generally avoid sitcoms and sitcommy movies entirely because I am so sensitive to the secondhand embarrassment thing, but if a situation pops up that I can’t watch, I will sit in front of the TV saying something like “blah blah blah oh Character don’t do that la de dah noooo” until it is over.

    7. Sara*

      I used to leave the room while watching Gilmore Girls with my college roommate and she’d have to tell me when the awkwardness ended. I can’t stand cringe humor.

    8. Murphy*

      Yes, I can’t endure some awkward humor. Neither can my husband. We were watching something recently and he just got up and walked to the kitchen going “AH! I CAN’T!”

    9. Jules the 3rd*

      yep, that’s me too! I can’t watch “Something About Mary” and similar movies because it is physically uncomfortable both at the time and in the future.

      This actually is a part of my OCD – my ‘obsession’ (instrusive thought) is often some embarrassing flashback. And I do mean flashback – I get all the same physical reactions I did the first time around.

      1. College Career Counselor*

        I see I am among my people! Couldn’t watch “After Hours” or large parts of “A fish Called Wanda” that everyone else thought was great.

    10. kible*

      I definitely get it while watching things (anime, movies) or reading it in comics/pictures, but not as much when reading things that are just words. It’s weird. I guess being able to picture it without using my imagination is what hurts.

    11. This Daydreamer*

      I’m in the same club. I mean, I’m okay when people are sharing a personal story for a laugh, but you couldn’t pay me enough to watch the average romcom.

    12. Elizabeth H.*

      Interesting – my boyfriend has this so intensely that he cannot watch any sitcom at all. I once tried to get him to watch a few minutes of Broad City and he eventually RAN OUT OF THE ROOM. He’s an extreme case (he has lots of other uniqueness-es about what he will, aka wont, watch or read) but I totally get this.

  42. shep*

    This was more networking-related than strictly work, but still absolutely mortifying. I was talking to a friend-of-a-friend acquaintance at a party who had a similar graduate degree in writing, albeit from different schools, and spent a good three or four minutes eviscerating one of my old undergrad professors. (He was an absolute jerk, incredibly condescending to me, didn’t think I could write, and the department head–who was very complimentary of my work–even asked me later if I thought he graded fairly and what my impressions of him were (spoiler: NOT GOOD).)

    When I was done, she said, “Oh. He was my mentor during my grad program. He picked me especially because he really liked my work.”

    I’m not normally a blusher, but I flushed so hotly and prickly and tingly that I’m sure I was bright red.

    Still doesn’t change my opinion of the professor, but GAWD I was mortified.

  43. Countess Boochie Flagrante*

    God, awkwardness is the worst thing for me. I suffer from severe embarrassment squick, to the point where I even have to turn off movies/TV shows if a scene hinges around someone being horribly awkward. Full-body cringe.

    Tragically, this doesn’t save me from having terribly awkward moments. I’m the queen of mis-clicking on things, and while I’ve not had a reply-all nightmare (yet! knock on wood!) I accidentally hung up on a very angry financial advisor when I was still in training, when I meant to put him on hold… because he’d asked for my supervisor! It had been a contentious call where the FA was asking me to bend the rules for his high-value client — and since I was so very new, I had no idea which rules were bendable and which were extremely rigid. (As it turns out, the one he wanted me to bend was a rigid one.) So it escalated, with him telling me in very profane detail how my line of business was the worst, how we were all idiots, how he wasn’t going to have his client inconvenienced by some little b***h… you get the idea. And finally, finally demanded my supervisor.

    I said, “Okay, I’ll get him, please hold.” And clicked “disconnect” instead of “hold” on my call toolbar.

    (In my defense, they were right next to each other and I was profoundly rattled. Still!)

    Well, he blew up my manager’s phone immediately — which my manager wasn’t answering, because the moment I realized what I’d done, I raced to my manager panicking at how hard I’d just screwed the pooch.

    End resolution: the client didn’t even care, the FA was being a gigantic tool, and I didn’t actually get disciplined! Just told “hey, try not to click wrong buttons, but you were 100% correct that you shouldn’t do that without speaking directly with the client and this guy’s manager is going to hear about his attitude.”

    1. paul*

      I hate the rise of cringe comedy; I physically can’t watch it. It’s absurd that it gets to me so much but I’ll literally find myself screwing my eyes shut and/or with my hands over my ears…never figured out why it does that.

      Also, our CISCO phones at work have the transfer, end call and hold buttons all right next to each other. Horrible UI.

      1. Countess Boochie Flagrante*

        Personally, I’ve always felt that it relates to some degree to levels of empathy — when you can read a room clearly, it’s painful to see someone stomp through in total oblivion. Admittedly, though, my sample size is a bit small :)

  44. Jilly*

    The most awkward thing that I experienced at work was the aftermath of an awkward event. One day at work I got an email with the subject line “A hug, a rejection, and a goodbye”. Basically an independent contractor sent a company wide email to explain that he had just been fired. Per the email he had been focusing on honoring his emotions and if he needed a hug he wasn’t going to deny himself. And apparently he decided he needed a hug and gave a guy in the bathroom a hug. Completely unsolicited. Said hugee was very, very, very introverted and possibly on the spectrum. He was very good at his job and very helpful, but it was absolutely understood that you emailed him your request – you didn’t go talk to him. And under no circumstances did you make him shake hands, much less hug. So the Hugee went straight to HR and complained and they fired the contractor immediately. When he went to get his personal stuff from his desk, he wasn’t escorted and had time to send this email justifying his actions. The email was quite detailed and completely oblivious to any wrong doing on his part. The OMGs were audible around the office (of about 300 people I think). And many of us started forwarding the email to our personal accounts because sure enough, once senior management got wind of it, IT deleted the email from the server and everyone’s work accounts. 15 years later, if I see someone from that job and say “a hug, a rejection, and a goodbye” they burst out laughing. Unfortunately I lost the email. I had forwarded it to my hotmail account which beginning in 2007 I kind of abandoned and only checked 2-3 times a year so I missed the fact that it was going to disappear. . .

    1. Future Analyst*

      Wow. This is so awful for the hugee, and so hilariously misjudged and oblivious on the part of the hugger. Glad the company fired him, but surprising that they didn’t escort him to make sure he didn’t hug anyone else!

    2. Rebecca in Dallas*

      Who hugs somebody (unsolicited) in the bathroom?!?!?! I’m not on the spectrum and I’d probably be running to HR, too!

    3. Countess Boochie Flagrante*

      Please tell me the huggee was just washing his hands or something, not using a urinal at the time…

  45. Sofia*

    Not all that awkward but probably a sign I shouldn’t be reading this website at work: in an email I called my manager Fergus.

    Her name is not Fergus.

    1. Detective Amy Santiago*

      And that’s when you desperately hope your manager doesn’t read this website (even though it sounds like she could benefit).

    2. Jesca*

      Haha I once kept texting my boss and referring to him as Patricia. That was not his name. He is a man with a male type name. I had been working with him for 2 years. I don’t understand myself.

    3. SusanIvanova*

      The VP of Engineering at my smallish company decided to make people move offices for no reason other than he had the power to do so. Coincidentally, it was shortly after the Dilbert cartoon where Wally brags about controlling cubicle assignments and calls himself “Lord Wally the Puppet Master”. (The 1995-04-20 strip on dilbert dot com). So someone referred to our VP as “Lord Fergus the Cubicle Master”, somehow he picked up on it without getting the reference, and he _signed off on emails_ that way.

  46. Mrs. A*

    I can’t wait to read this book! Here’s my story: My husband and I had been trying to have a baby for years (we now have a gorgeous 1 year old) and had decided to seek fertility treatments. One day, I was walking out of my appointment and who do I see walking down the hall towards me? One of my coworkers! We had always been friendly but definitely weren’t on that intimate level. Our eyes met and both of our mouths dropped open. I was embarrassed and then curious and then excited (because infertility makes you feel super alone). I grabbed her hand and enthusiastically said “Let’s talk later!” And then was kicking myself, maybe she doesn’t want to talk about it, ugg we work together and now I know something extremely personal…… Anyway, that super awkward moment turned into a lovely friendship and we now have regular play-dates with our kids.

  47. The Other Dawn*

    Mine happened when I was only about two years into my career. I was working in a pretty big bank as a teller manager and many of their branches had just been marked for divestiture, meaning they were sold off to other banks because the local market was saturated; you don’t need two Large Bank branches on opposite corners. Until my branch changed hands, I had to attend monthly meetings that were for other branches of this bank that were sold, as well as other banks involved. The meeting was run by someone who was kind of a district manager and was the one to oversee the branch operations for all the branches involved. She was quite young, maybe 22 or 23, as was I. I aspired to be in her position one day and was thrilled when she asked if I wanted to go to lunch with her while she was on site that day. We went to a little diner next door. We chatted about various things and she mentioned how one day she wants to go back and finish school. Stupidly I asked, “High school?” She said, “No, college.” Since no one in my family had gone to college, including myself, and a few of my siblings as well as my parents had dropped out of high school, it didn’t occur to me that she was referring to finishing her college degree. I really wanted to crawl under the table. Luckily she didn’t let on that I’d said something really idiotic and let the moment pass.

    I’m still That Person, unfortunately. Things just come out of my mouth and I have no idea why I say them. I’ll be talking and things are going fine, and then I try to one-up myself or keep the flow going…and I stick my foot in my mouth every time.

  48. Secretly awkward lawyer*

    I once had to ask my assistant (middle-aged, moderately overweight) to please stop wearing a too-small shirt that would ride up and expose her undergarments. She told me that she knew it was too small, but didn’t want to waste money by getting rid of it. She told me this while kicking off her shoes in my office and rubbing her bare feet.

  49. Jen*

    I work at a college bookstore and we hire a lot of temporary workers for the semester start. It doesn’t pay much, so we regularly scrape the bottom of the barrel when it comes to temps. I was desperate and did a short 5 minute interview with a walk in applicant who seemed promising enough. He told me he also had a friend that needed work and their availability fit with what I needed. I hired them both, put them on the schedule, and didn’t think too much more about it. Their first day, both guys showed up (on time! yay!) but were dressed in Jamaican style with wigs. They then spent the entirety of their shift speaking in fake accents to customers about “island life” and weed. They were both white Americans.

    My boss was not impressed. I didn’t invite them back.

    1. Snark*

      I’m trying to imagine being so high that it seemed reasonable to think “It’s my first day at work! I shall put my best foot forward by putting on a dread wig and making racist jokes LITERALLY ALL DAY.”

  50. Front Desker*

    At about 2 pm on a Tuesday, my BF of two years sent me an email breaking up with me. The next person I saw was the FedEx guy who I had a semi-crush on. He asked how my day was going and I burst into tears and told him I just got dumped. He felt so bad for me that he gave me a hug! My manager sent me home after that as I was clearly too much of a mess to deal with people.

    But seriously, who dumps someone over email?

    1. Funbud*

      Well, Carrie Bradshaw got dumped via post-it note on “Sex and the City”.

      And Alison Arngrim (who played mean Nellie Olsen on “Little House on the Prairie”) divorced her first husband via fax. Seriously. You can read it in her great memoir “Confessions Of a Prairie Bitch”.

    2. Clewgarnet*

      I got dumped via /query in an IRC channel. He told me he’d just got engaged.

      Another time, I came home from work to find a Word document open on my computer, with a long-winded version of, “You’re dumped.” (We didn’t live together – he lived in a different country and was visiting for the weekend.)

  51. Flinty*

    As a new social worker I was conducting a home visit with one of my clients, who only spoke my second language, which I was a little rusty on at that point. After checking their bathroom for safety bars, I told them I would go write (my notes) in their living room. It was only after they stared at me in complete silence I realized I had accidentally told them I was going to go piss in their living room. Mortified.

    1. Future Homesteader*

      Russian? I did that to my host mother. (I told her I was practicing Russian in my bedroom…by pissing!)

      1. Flinty*

        Yeah! I think everyone learning Russian has at some point made that mistake, or the one where you say you prefer to eat food without condoms :)

        (preservatif = condom in Russian)

  52. August*

    Oooohhh my god. The most awkward experience in recent memory was when I finished up a meeting with one of my organization’s community partners, a lovely man who runs a Mexican dance-centered organization. When we both stood up to leave, he (casual guy, Hispanic, works primarily in the art/nonprofit community) held out an arm in what I (white, anxious, receives approximately 4 hugs a year from my mother and my mother alone) assumed was a handshake. Instead, he ended up sort of pulling me forward into a kind of stumbling quasi-hug, where my outstretched hand ended up in his gut, my chin was hooked over his shoulder, and my feet landed right on top of his feet. In retrospect, it probably would have been easily laughed off had I not panicked, squeaked “my meter’s run out, I’ve got to go!” and bolted from the restaurant.

    [shrug emoji]

    1. dr_silverware*

      Whew–those kinds of interactions between low-physical-contact cultures and high-physical-contact cultures are the worst for this kind of awkwardness. Even when you think there’s no cultural split between you and your friend’s family, and then your friend’s mom goes in for a French air kiss, and you’re 14.

  53. bunniferous*

    At a former job, one of the owners died. Let’s just say it was awkward when sales people or others would call or stop in and ask for her… no unawkward way to tell someone the person they insist on speaking to is dead.

    That same job, one of our florists died suddenly smack dab in the middle of corsage season. Yes, dear helicopter mom, little Johnny has to wait for his date’s corsage a bit longer since we are shorthanded….I finally had to tell a room full of aggravated people WHY we were shorthanded. Awkward!

    After that, I don’t get fazed by much workwise anymore!

    1. Not a Morning Person*

      I’m so sorry! That reminds me of a not so tragic situation, no one had died: I had an appointment with a client at one of his businesses and when I showed up to ask for him, the receptionist said, “He’s no longer with us.” That made me think he had died since we’d made the appointment! I dithered around and made some kind of confused excuse that we’d had an appointment and was there someone else and the receptionist said no. So I left and went outside to confer with my colleague (the meeting was to do some work outside on their lot). We spent just a couple of minutes commiserating about what to do since our client was apparently deceased, and then the client walked up to our van and waved at us. He wasn’t dead, he’d just moved his office to one of his other businesses. I have no idea what his receptionist was trying to convey to us, surely not that he was dead but perhaps that he didn’t work there? But he was the owner!

    2. Faith*

      Ooh that reminds me of another awkward story I’d forgotten about. At my first job, during my first or second week, I was assigned the task of calling all of the former winners of an award my organization gave out, to invite them to attend our upcoming conference. I really hated talking on the phone (still don’t love it, but I don’t actively hate it as much as I did back then), so this was already giving me a lot of anxiety. Still, I got through the first several calls OK.

      But then I called up one place, identified myself and the organization I was calling from, and asked if I could please speak to Jane. Silence, then finally, “…Jane passed away a year ago. I thought you knew that?” I was mortified and quickly explained that I was new at the job. My coworkers did know that Jane had died, but had forgotten to tell me/remove her from the list. They followed up with the organization I’d called to further explain, and there were no hard feelings or anything, but I was so embarrassed.

      1. bunniferous*

        As someone who had to field calls like that, trust me, we understand. I would have thought everyone knew about MY boss since her battle with a brain tumor had been in the paper and everything, but it happens. No worries!

  54. Petite Noob*

    I had a one on one meeting with a coworker in a huddle room. After we got through our topic of discussion, he said “Oh, Petite Noob, I knew an actress with your same name in the 80’s. I’d definitely rank her a B+ or an A-…” I had no clue what to say so I just went with, “Oh yeah…” Then he went into detail about how cute the actress was and how similar we looked.

    I promptly left the huddle room and that gentleman has never made eye contact with me since and meetings are now super awkward.

  55. Temperance*

    I’ve shared this story before, but it’s the epitome of awkward.

    I was attending Booth’s holiday party as his +1, and was prepared to do the polite networking thing. He introduced me to a couple and mentioned that their daughter had just gotten married, and I congratulated them. I thought this guy was their CEO, so when his wife whipped out the photo albums, I rolled with it and pretended to be interested in seeing 300 photos of strangers eating in what looked to be a firehall.

    She pointed out her 3 daughters, and told me how proud she was that they were all virgins and how she raised them to be pure for their husbands. She then told me how the groom’s brothers pulled her aside to let her know how her daughters were all “nice girls” and they hope to meet pure women when they get married, too.

      1. Temperance*

        The more hilarious part of it was when Booth’s friend also looked at the pictures and later yelled THERE’S NO WAY ANY OF THOSE GIRLS ARE VIRGINS

        1. boy oh boy*

          I almost never laugh out loud at stuff online but this has brought tears to my eyes…

          Who was the couple? I assume not actually the CEO and his wife?!

  56. Can't Believe I am admitting this*

    The most awkward/embarrassing moments of my life have unfortunately involved me being sick to my stomach.
    Last year I flew to Europe. Prior to getting on the flight I had two beers in the airport. Unknown to me was that this beer would not agree with me at all. Going thru the flight I kept feeling worse and worse but I kept thinking that I could make it off the plane to the airport. As we are sitting taxing to a gate – whoosh I end up vomiting all over myself and the person next to me. I ended up trying to clean myself up in the plane lav while everyone left. I then bought a complete change of clothes at the airport and continued my travel on another flight. Now before being accused of falling down or the like a person I was travelling with who also had two beers at the same place as me had digestive issues and made a beeline to the airport on deplaning. We blame the bar in the airport for not cleaning the tap lines.

    Now the other incident involved me and my future FIL but that is for a different time.

    1. Coalea*

      I was returning to the US from a business trip in Japan and found myself struck with motion sickness during our initial descent. The restroom door was locked. I searched desperately for an air sickness bag, but there weren’t any available, so I ended up vomiting all over myself and the aisle of the business class cabin. I was able to throw my blanket and pillow over the mess in the aisle, but I had to sit there, filthy, for several minutes. As soon as the plane touched down, I yanked my bag down from the overhead compartment and changed my shirt right there in my seat. The only silver lining is that none of my colleagues or clients were on my flight, so they were spared this horrifying sight.

  57. patricia*

    Lunch meeting with a prospective client (someone I already knew personally- had previously worked in his organization- now just trying to get him to hire me after I’d moved back to private practice). He invites me to walk back to his office so I can catch up with other former colleagues- it’s a couple blocks. I’m wearing my “I’m at lunch with a client and don’t expect to be walking anywhere” heels, and can’t figure out how to gracefully slip on the “I had to fly here and wouldn’t be caught dead in heels in the airport” flats I had in my bag. So I gamely huff and puff over a couple blocks of city streets, dodging subway grates and sidewalk cracks, trying to keep up with my client, who is wearing sensible shoes as men do. I’m almost there- it’s across the street- and we have to stop for a red light. I end up on the wheelchair curb cut, and just the slant is enough to unbalance me. I teeter to the right, almost catch myself, totter to the left and backward, and feel myself going down in slow motion. I can observe each leaf on the trees fluttering individually as I descend. End up falling into the street and cracking my head on the pavement. The worst is that I have NO idea how much my skirt rode up- I scrambled to my feet as quickly as possible and pulled it down- but there’s a significant likelihood that my client was made all too painfully aware of the existence of my “off to see a client” shapewear.

    Client did hire me, on the condition that I wear flats forever more around him. He brings it up multiple times a year, so I get to relive that on a regular basis.

  58. ThatOneRedhead*

    I was an RA in college and told a freshman’s parents that I hoped their hotel had clean sheets. In front of my boss.

  59. Whipped Cream*

    This was at my second ever Real Job, which was a supremely toxic work environment. We hosted an event annually for our members that was a very large amount of work, and on the last evening of the event there was usually a free bar for event attendees and organizers to go to. So the team and I are chilling out in there, and our Boss/CEO rolls in about an hour after the rest of us had arrived, already quite liquored up. The bartender of the evening had just started trying to convince a bunch of the party people to do a shot which involved whipped cream and consuming it without using your hands.

    Boss thinks this is a GREAT idea, enthusiastically encourages the team to do it (admittedly I partook because, well, I was young and unaware of what a non toxic work environment could be like). Anyway, Boss is drunk enough to start that somehow she manages to get the whipped cream on her back?? while doing this shot. And doesn’t notice for at least half an hour, during which the team and I keep snickering to each other (a large part of the toxicity was from her leadership). I was partially embarrassed for her and how inebriated she already was at a membership event, but also was enjoying some pettiness at her making a fool of herself with the board in the same room.

    1. Whipped Cream*

      email! Also I forgot to mention that Boss showed up with her hair tousled from a romp with previous past president of the board, at least according to previous past president. Ugh.

  60. IKnowRight?*

    One of my colleagues generally works an earlier schedule than I do, so we’re rarely alone in the office together. One evening a few months ago, we were the last two people in the office, and out of the blue, this person asked me “Do you hate me?” (Side note: this person has talked about mental health issues that could explain why they might incorrectly believe people don’t like them, so I wasn’t 100% caught off guard.)

    I was horrified, and pretty much wanted to leave the office ASAP. Instead, I told them no, and we talked about it in a way that I think was helpful for us both, but it was easily the most awkward situation a colleague has ever put me in.

    1. JeanB in NC*

      I mean, what can you say to that? “Yes, I hate you – every time you staple something I think there’s a bomb going off!”

  61. Horse Lover*

    Okay, so my first job was as a bank teller. The branch I worked for had 3 sets of sister-in-laws working there and they brought their family drama with them every day. One of these sister-in-laws was having an affair with our branch manager and the other side of her family vehemently disapproved.

    So, one day Sister-in-law #1 was “in a meeting” with the branch manager in his office. Only, we could all see in the glass windows they were not in his office. They were in his private bathroom. Sister-in-law #2 needed branch manager for actual work and stood, beating on his door and ranting for the whole branch (customers and all) to hear about what they were mostly likely doing in there, how SIL #1 was a harlot, details of the whole affair, etc, etc. It was painful and went on way too long before anyone was able to get her to stop and leave. Then branch manager and SIL #1 just calmly walk out of his office and carry on with their day like nothing happened.

    There were so many awkward moments there, but this is the first one that came to mind.

  62. an infinite number of monkeys*

    About 25 years ago, when I was a mere slip of a corporate shill, we had a new guy start on our floor. Word around the office was that he’d recently tried out for, I think, American Gladiator? He was athletic and had what I would later come to think of as “marketing hair.”

    One day I crossed paths with him on the way to the elevator, and looked back over my shoulder to check out his butt. He was turned around doing the exact same thing. Our eyes met. There was a Moment, but it wasn’t sexy and endearing like a romcom. It was just uncomfortable.

    I’m much more discreet now that I’m older.

    1. Montresaur*

      Ha! “… when I was a mere slip of a corporate shill” is my new favorite idiom mashup (surely there’s an official term for that kind of wordplay? Will investigate)

  63. Jesca*

    I know I posted this before, but I will again.

    I was once working at a place with a boss who kept heaping tons and tons of work on me and then complaining why my actual job tasks were slowing (ya know – that old tired story). Well one day she was going on about this while I was at my desk and I just whispered “I quit”. She asked me if she heard me correctly, and it was so awkward that she heard me that I just responded with “I quit”. AND THEN to add a touch further awkward to the mix, picked up my bag, gave her this kind of dismissive wave, and with a casual “bye” I walked out … never to be heard from again.

      1. Jesca*

        I literally did not tell anyone for years how I left this job! Not even close friends. I mean, I still don’t understand any of it. Alison, this is why I need this book!!

  64. Anonymous for this*

    This one’s not that bad in the grand scheme of things but it’s the best I can come up with right now.

    I was asking a manager in our department about our dress code and culture because I wanted to know if there would be a problem if I wore a skirt with unshaven legs when the dress code was business casual. What I meant to add was, “I don’t mind being seen as a raging feminist.”

    For some reason, my mouth replaced “feminist” with “lesbian.” Which statement is also true, but wasn’t the effec tI was going for.

  65. Revolver Rani*

    This wasn’t technically at work – it was in the Law Review office when I was in law school, which in some ways functions like a workplace (but in other ways does not). I hope it counts for an entry into the drawing. :)

    The background is, years before I ever went to law school, I had been interested in a woman and asked her out. She let me down very gently (she didn’t share my proclivities, and anyway was involved with the man she later married). She really was very kind and lovely about it – an “I’m flattered but…” sort of response that just struck me as deeply sincere. Fast forward 6 or 7 years and surprise! we are in the same law school class – a different university from the one at which we met, in a different state; just one of those funny things life does to you.

    Reader, I still liked her. Not enough to break my heart, not enough to ask her out again, but enough to make me a little stupid around her. When we both joined the Law Review staff I we ran into one another quite often, and so I had lots of opportunities to say awkward things to her – and I took advantage of them. One that I remember with a particular cringe was when she came in having cut her hair into a short style, one that was a little unusual at the time, a little throwbacky (think Audrey Hepburn pixie cut), and it was very attractive on her. I wanted to compliment her on the uniqueness of it. I told her it looked very good. And then, I added:

    “It’s not really in style these days, but it looks great on you.”

    1. Turtlewings*

      “I had lots of opportunities to say awkward things to her – and I took advantage of them.” A+ phrasing. Beautifully mortifying comment. Excellent post.

    2. overcaffeinatedandqueer*

      Awkward law review moment for me:

      Four women staffers, one dude. Someone asks for meds for period cramps, dude is feminist so doesn’t say anything. Then the women and I start complaining about periods. We are all eating leftover pepperoni pizza.

      Someone mentions how the clots are the worst, how they can be as huge as a quarter or bigger, how gross it is.

      Sole guy pushes his pizza away, literally green, and groans, “I can’t look at pepperoni right now!”

  66. LeeGull*

    Oh my gosh, I want to win but if I don’t I think I need to buy this book anyway!

    I once went for a handshake…and you know how you sort of catch thumbs and then shake? I missed his thumb. And grabbed his wrist. And then neither of us knew what to do so I just awkwardly shook his wrist and then backed away and tried to avoid eye contact. Like forever. Like I still don’t think I’ve made eye contact with this person since.

  67. Dixie Thursday*

    I was a young admin, not yet very confident or comfortable answering the phones when one day a guy was leaving a message for my boss. He gave his phone number, followed by a five- or six-digit extension number. The guy then went on to explain that he was just a “little guy” in his organization, to which I responded, “Well, for a little guy, you sure do have a big extension.” My cubicle mate, only hearing MY side of the conversation gasped loudly and I was instantly horrified at what I’d just said. I cringe to this day, 30-plus years later!

    1. Coalea*

      Many years ago at a previous job I was having problems with a database. The IT guy watched me demonstrate on my own laptop and then asked me to try and open the database on his machine to see if the same error occurred. For some reason, he had this crazy little mouse, and as soon as I started using is, I exclaimed, “wow, I’ve never touched such a little one before!” The entire IT department busted out laughing, while I silently prayed for death.

  68. JB (not in Houston)*

    At my boss’s wedding shower. My first office job after college. That job was terrible (we used to say that we all wanted to work at the company where our internal recruiter worked, but the place she described to us in interviews and where she seemed to think she was working was not at all the reality of where we worked), but that’s a story for another day. At the shower, I was sitting next to my boss, which was awkward enough. That it was a lingerie shower was also very awkward, but I could handle it. But when she opened my gift, she leaned over to hug me to thank me. From the angle she she leaned in toward me, I thought ‘oh, ok she wants to do that European thing where you kiss each other on the cheek. That’s weird,” but I didn’t want to obviously rebuff her in front of everyone at her own shower so I panicked and went with it. You can see where this is going. She was not, in fact, leaning in to do a cheek kiss, she just leaned weirdly into the hug. Fortunately I realized very quickly that she just wanted a hug, but unfortunately not until the exact moment I gave her a light, my-best-approximation-ofwhat-I-imagined-was-a-“European-style”-kiss on the cheek. I tried very hard to play it off like no big deal while simultaneously willing a hole in the ground to swallow me up. She didn’t make a big deal out of it, thank God, but I could never really look her in the eye after that.

    Years later, there was an episode of Friends where Rachel does the same thing with her boss, and I still cannot watch that episode on reruns.

      1. JB (not in Houston)*

        Fortunately, she didn’t make a big deal out of it. There was kind of a pause where I could see from her eyes she thought it was awkward and strange, but she then immediately started talking about and opening the next present while I sat there unable to hear or see anything because of the overpowering mortification. Later in the party we had to do that game where you choose teams that compete to make a wedding dress out of toilet paper. Of course my team chose me to be the person getting tp’d, which made things worse for me because the last thing I wanted was for anyone to look at me or even remember that I was there. I don’t remember if our team won, I just remember wanting to Incredible Hulk myself out of the toilet paper dress, run out of the party, and never return to work.

  69. Anonish*

    I used to work in the headquarters of a paint and sip event company. My aunt was in town from another country for a family wedding, and she and my mom were having lunch nearby so they dropped in to visit me at work. In a room full of my coworkers (and covered in paintings from our events), she asked in a loud voice, “So what IS a paint party?” I gave her a quick explanation to which her response was, “Well, who would ever want to do THAT?”

    Thanks for your opinion about how we all make our living, Aunt P.

  70. Chylleh*

    Years ago I ran into an awkward situation while working in the children’s department of a library. A young student was doing a project on taxonomy and asked an employee for books about the subject. The research eventually led to her, the student, and myself trying to find a book with the animal kingdom hierarchy chart for his project.

    The student ran off to bring a book back to his table where his family was, and another coworker came over to see if she could help. Original coworker said we were looking for a taxonomical chart, and explained, “It’s about animal classification. You know – kingdoms, phylums, orgasms, that kind of thing.” We all shared a moment of stunned silence while her face turned an increasingly deeper shade of red as she realized what she said, then all of us burst into laughter. We were just glad the student and his parent were away at the moment.

    1. Chylleh*

      Annnnd I forgot my email address in the last post. I promise this isn’t an attempt to create another awkward moment, game the system, and get two entries.

  71. The Ginger Ginger*

    Oh man, this book sounds awesome!

    My first job in highschool, I worked at a jewelry store in the mall that also pierced ears. One afternoon a very big, fit, late highschool/early college age guy (looked like a linebacker) came in with his mom. They split an ear piercing pack. I pierced mom’s ear, then the guy’s ear. Easy peasy, cleaned the piercing, gave them the whole memorized spiel about care, and called it done. Guy stands up from the piercing chair so they can go pay and PASSES OUT. Hits the floor like a load of bricks, takes down an earring display, the whole shebang.

    I didn’t feel awkward myself as I went into triage mode, busted out the smelling salts, cleared the floor, sent a coworker for a sugary drink, all that. But I still can’t help thinking how mortified he must have felt, passing out in front of his mom and this little 16 year old girl – and half the mall – from getting his ear pierced. Poor guy. (Of course, now I understand all about vasovagal syncope, because I’ve brushed up against it myself a couple times, but man, the sympathetic cringing is REAL.)

    1. zora*

      [raises hand] Vasovagal syncope over here!!!! I super know how that guy feels!! ;)

      What’s funny with mine is, if it’s just me, I’m fine. But seeing someone else get ‘stuck’ is way more likely to make me pass out! So, in his case, it would have been because my mom was there, not because I was getting pierced. It’s so weird and so much harder to explain!

    2. JDusek*

      That happened when I was 10 years old and my aunt took me to get my ears pierced for my birthday. Afterwards, we went to Hallmark in the mall and my aunt saw me fainting and caught me. Took me to sit down and I threw up.

    3. The Ginger Ginger*

      Mine isn’t even needles necessarily; I’ve had some issues with it when waiting for procedures – like getting my wisdom teeth out or when I had a cyst removed in an outpatient surgery. There’s something about getting a jab while ALSO stressing out just waiting for the procedure that lays me out. Blood donation? Flu shot? Totally fine. Leave me alone to stew about impending sedation then come in and stick me with the IV? I better be horizontal or I will find my way there in spectacular fashion.

    4. Adlib*

      Been there. I used to have this reaction every time I got a shot or had a blood draw. It finally went away when I had multiple tests for some health issues I was experiencing which led to a spinal tap. After that, no weird reactions to needles. I’m so relieved!

  72. CoveredInBees*

    I worked at a nonprofit for a CEO who was not careful about talking about “touching” donors as in being in contact with them about our work and their interests. She also repeatedly talked about not being dressed when what she meant was “dressed up”. I was on a call with her and a prospective funder when she mentioned that she and I weren’t dressed. I jumped in to clarify she was referring to casual Fridays but I’m pretty sure I could hear the poor guy blushing.

    The funniest was when an attorney (thankfully, not me!) said, “Thanks, I love you too.” to a judge. He was distracted and said it in a way like he was ending a phone call with a loved one. The funniest part was that it took the judge a few beats to notice. I am certain that there was nothing going on between the two of them but they were very careful after that.

    1. Revolver Rani*

      I worked with an attorney who once said “okay goodnight, love you” to a partner (meaning, a partner in the law firm) at the end of a phone call. She had been working hard all day taking a deposition, and was tired, and had called the partner from the airport to debrief, and just kind of automatically signed off the call the same way she would to the person she lived with.

  73. Languages Are Difficult, Okay?*

    My boss had the entire team over to his house for a dinner party. At some point I — the youngest person there, the only woman, and the only non-native speaker of the relevant language — am telling a story about my day, in which a moderately-famous older gentleman had become mildly annoyed at me over something trivial.

    My co-worker chokes on his drink. “This guy did WHAT?!”

    I repeat what I said, which I thought translated to “he was mildly annoyed at me.”

    Dead silence, followed by nervous laughter. I look around, and everyone was blushing.

    Eventually, someone explains that the phrase I was using didn’t mean that the guy was annoyed at me. Instead, I had just announced to my entire team that a moderately-famous older gentleman had performed oral sex on me.

    1. 2ManyBugs*

      You were reaching for “chewed me out” and missed, right? That’s the only colloquialism I can think of!

  74. The future will be better*

    I work in a profession that involves frequent use of rented company vehicles… Due to medical reasons, I had VERY heavy periods. I once realized I bled through my work clothes, and drove back to work to make sure the truck was okay… It was! But imagining explaining that to my (male) boss was one of my cringey work experiences, and I believe we all need to talk more about periods.

    I also casually chatted with an office boss like he was a fellow on worksite guy once (casual language and likely some cursing), because my old phone showed the wrong number. Eek!

  75. Kadi*

    I have so. many…. but, the worst for me still is when I was 9 months pregnant. I sat in a chair across from my boss’s desk. My legs always had to be sticking out to the side a bit to make room for my belly. She kindly pointed out that I had somehow unknowingly split my maternity pants at the crotch – and my white underwear were clearly showing through my black dress pants. Awesome. Maybe that’s more embarrassing than awkward?

    1. Close Bracket*

      Ooh, visible underpants stories! One day on my way out of the office with my hands in my trouser pockets, I passed passed a coworker walking the other direction and gave him a cheery “Good night and have a good weekend.” He didn’t respond, but he did a very small double take. I thought nothing of it until I got to my car, got in, sat down, looked down, and saw that my fly was all the way open and my red underpants were like a shining beacon framed by my black slacks. I had a moment of mortification and then laughed hysterically. I knew he would never, ever say anything to me about it and promptly put it out of my mind.
      I actually felt a little bad for him bc I am a woman and he was a proper Syrian guy. He was probably more embarrassed than I was.

      1. Cate*

        I can’t recall if this happened to my friend or if he was relating a story about a colleague, but whoever it was he learned the hard way to only wear black boxers when playing the Phantom (in Phantom of the Opera, on Broadway) when his trousers split and he had to do the entire final scene with red boxers on display through a knee-to-crotch hole.

  76. VelcroShoes*

    I went to France to work in a museum/post-office (It was a very unpopular museum of the postal system in the morning and a fairly successful post office in the afternoons. I was sent by my mother in a misguided attempt to instil in me a love of French culture – it paid off in that I now have a deep seated desire for brie when posting things and can swear broadly about stamps in perfect French.)

    On the first day, the other women who worked there offered for me to go out for the lunch break. I was an anxious teen (and now an anxious adult!) so I politely declined and hid inside to read my book and eat my packed lunch. The two women smiled at me (French-ly…?) and started nattering away in fast French as they sauntered off for a (very long) lunch break, locking the door behind them.

    1 hour 30 later they returned and life resumed as normal. But in that 1 hour 30 I’d discovered dusty old museums of the post office are kind of terrifying and I desperately wanted to be outside in the sunshine. Particularly when a large dusty model of a French postal worker from the 1940s crashed over with no encouragement… It was spookier than it sounds! I made a decision to bite down the awkwardness and tell them the next day that I wanted to go explore.

    So the next day, as lunch rolled around I took my heart in my hands and prepared to tell them I wanted out… Except, without asking, they simply left. And locked me inside. Staring balefully out at the summer weather, I was well and truly trapped inside without any lunch whatsoever. And the pattern repeated every day for the next two months (luckily I got my weekends off). By the end I had learned to pack my lunch.

    Awkward an encounter as that was, the worst moment was when a visitor tried to visit the museum during lunch. Seeing me haunting the inside like a pale chubby English ghost, they could NOT understand why I wouldn’t let them in (the French are passionate learners of postal history, clearly). He spent a good 10 minutes staring through the glass door, trying to gain access to my carefully held treasure trove of knowledge. He became really quite frustrated with my apparent lack of willingness to share my dusty prison, as I stared awkward and blank, unable to communicate my complete lack of keys.

    If only he’d known how pleased I would have been to swap.

    1. Eye of Sauron*

      This hands down is the funniest story I’ve heard/read in a long time.

      THANK YOU! I really needed it today :)

      1. VelcroShoes*

        Maybe they thought I should just give my life for the sake of French postal history… There might have been a fire exit, honestly it was about 15 years ago so I can’t remember!

  77. beanie beans*

    I can’t wait to read through all of these later! Here are my two most awkward work moments:

    1 – Boss stops by my desk while I’m struggling to get my hand unstuck out of a Pringles can.

    2 – I was listening to a webinar so I decided to french braid my hair into two braids while I watched. As soon as I finished one, my grand boss stopped by my desk for a chat about a project. We had maybe a 5 minute conversation and rather than unbraid the braid, I sat there through the conservation with one side of my head braided and the other side down.

    1. ggg*

      Once I stopped by the desk of an admin at work, as she was taking out a weave. There she sat, talking to me, in the middle of the work day, with half a head of hair and a trash can full of weave remnants.

    2. Boy oh boy*

      Pringles can just made me snort on the train because the awkwardness is so relatable and the mental image is so funny.

  78. LittleRedRidingHuh..?*

    Oh my, where to start?

    Let me tell you about that time when I decided to look cute in work, and for the first time in years, wore a skirt – only to tuck it into my underwear by accident after using the bathroom…and then walking back to my desk in front of our CEO giving a tour to potential clients. And if that wasn’t already enough, one of them remarked in a very matter of fact tone that it was very unusual to see a full moon this time of the day. Cue to me excitedly running to the window and asking: Oh wow, really? Where?

    Thankfully my CEO had a good sense of humour, gently told me about the “situation” and kindly let beet-red faced little me go back to work. I couldn’t look him in the eyes for quite some time and never wore skirts to work or elsewhere again.

    1. Detective Amy Santiago*

      I once had a very kind woman chase me down in the hallway outside the restroom to let me know that my skirt was tucked oddly and not covering my behind.

      1. AvonLady Barksdale*

        I am still mad about the time a co-worker DIDN’T tell me about my skirt tucked into my Spanx. Still mad. It was about 8 years ago and she wasn’t a very nice person anyway. I vowed to always say something, gently, even if it’s awkward.

        1. Clewgarnet*

          I once ran up an escalator at a railway station to tell a total stranger that her skirt was split.

          I didn’t tell her that a group of men had been following her through the station leering. We were ‘coincidentally’ going to the same platform, and they stopped following once she had company.

    2. Murphy*

      I got a dress stuck like that in the bathroom once. Thankfully, there was another woman in the bathroom washing her hands at the same time and she said “Um, I think your dress is caught on your sweater.” I realized what happened and said “Thank you for not letting me go out like that!” I’ve gotten over it, but I don’t really know this woman and I felt awkward for a little while after.

  79. StillBlushing*

    Imagine me… young, mid-20’s year old female, having a good day.. just cheerfully walking down the hallway at work and swinging my arms a bit (I don’t remember why, but clearly I was having a good day!). My older male supervisor is walking towards me… unfortunately my swinging, cupped hands happened to intersect with his body at the exact moment and I ended up CUPPING HIS GENITALS! I honestly think I couldn’t have done that if I was trying, but yep.. I managed to do it. He kept walking, I stopped with a look of horror on my face and he just said “no no” and kept going. Yes, I now keep my hands close to my body at all times!

  80. Sarah*

    A manager in our department was about to go on maternity leave and a card was making the rounds. I didn’t know what to put in it (about 20 people had already written “congratulations!”) so I wrote “well done!” Still cringing 5 years later.

      1. Live and Learn*

        I like it! When I was 8 months pregnant my husband and I went to a concert at a small local club. We were sitting at the back of the venue chatting with (VERY drunk) strangers at the next table over and they somehow didn’t notice my condition until I stood up to go to the restroom. When I stood, the drunkest guy yelled out “Wow! Congratulations dude, your seed is strong with that one” while pointing at my husband.

  81. Kate*

    I was at a kickoff meeting for a new project where I would be working with woman I had never met before. There were only about 5 of us in the meeting, her and I plus 3 other colleagues, and at one point she started giving me these weird looks from across the table. Like she kept motioning with her eyes, and I kept thinking, “What the hell is wrong with her?” Finally I look down to find three (THREE!) of the buttons on my shirt had come undone, so basically my bra was just out there for the world to see. Luckily, the other three were so wrapped up in discussion that they didn’t notice me rush to fix it. We only had one other meeting after that, and then I guess that portion of the project died, but we are bonded for life now.

    1. Samiratou*

      Oh, this reminds me of an awkward-for-all moment in a meeting once. Woman leading the meeting across the table from me had a button come loose so she was showing a bit of bra, if viewed from the correct angle (which pretty much all of us were because we were sitting to her right or right-ish and the projector screen was to her left). I sat there trying to find a way to bring it to her attention that wouldn’t draw MORE attention to it. She noticed after a couple minutes and chastised us (gently) for not letting her know and both I and the woman next to me protested that we had both tried to think of a way to let her know but couldn’t come up with one. Table was too big to nudge her under the table, she was presenting so no quick IM, she was looking at the projector screen and not at us for a Significant Look, and she was kind of on a roll so there was no lull to do a quick throat clear and clothing adjustment to try to let her know. Literally the only way we could have let her know was to interrupt “Hey, J, your button is undone! You might want to fix that!” which would have been as bad or worse, I think.

    2. boy oh boy*

      Oh no. This reminds of the worst wardrobe error I’ve made.

      So it was quite hot in the office. No air conditioning. There were nine people in a tiny conference room for 12 to 18 hours a day working on a huge project. We run small fan that does very little, we buy ice cream, drink cold drinks, etc. It’s nasty but just about okay.

      One foul, baking hot day I start getting PMS, which makes me super sweaty and I start feeling like I’m being roasted alive. I fan myself, have some cold water, and finally take off my thin button-up cardigan, leaving my vest top. It’s not ideal, but not obscene, and everyone’s too tired and sweaty to care, right?

      Nope. When I pop to the bathroom a day later, I realise my vest top is kind of translucent, and all could see my nice bra with a pretty pattern of cherries on it.

      I cringed like hell, threw that top out and wore thin silk/cotton blouses for the next three weeks.

  82. Eye of Sauron*

    I have 2, one mine and one related to me by my boss.

    1. Mine: I was running up a public but out of the way flight of stairs one day, I should note that I took these stairs daily and had never seen another person on them in the 2 years I worked in this building. As I was careening around the corner late for something I crashed into a man who was also in a hurry running down the stairs. Of course he had a handful of papers that exploded all over the place plus a two men flanking him from behind that crashed into both of us. My lunch was launched all over the stairwell. As you can imagine it was quite the chaotic scene. Once the papers settled and we all helped each other stay standing, I finally looked up.

    Hello Mr. Governor! Why yes, I had just crashed into the Governor of our state. Seriously, what are the odds?! Worst part was is that I got into trouble for returning late to lunch. I didn’t even bother to try and offer my excuse, who would believe it. I think I mumbled something about tripping in the stairs.


    2. We’re at a large 500+ person expo put on by my company for our customers. I’m talking to my boss who is wearing a horrified look on her face and oddly a different suit than she had been wearing in the morning. She pulls me aside and tells me this tale.

    “I was at a lunch meeting (catered burrito bar) with Teapots inc. and Fergus our account exec that handles the Teapots inc account. All of a sudden and without warning Fergus spews/throws up guacamole all over the two people sitting next to him and me! It turns out he was choking on the guac and his body expelled it*. It was awful, it looked like the scene from the exorcist. Guac was hanging from one of the client’s long hair. I had it all over me and had to change”

    *He was ok after he dislodged the guacamole but it was a serious situation

    1. Eye of Sauron*

      Oh wait… I remembered another one. (seriously I’ve been trying to forget it).

      I was sitting in a conference room talking to one of the contractors assigned to my project. There was another guy in the room with us who worked with me at my company. Anyway, I was sitting next the contractor, and had taken a big gulp of water, right as I had a mouthful and I was going to swallow, a stealth cough came out (I had been getting over a cold) and spit the water straight in to his face.

      OMG I was mortified!

  83. Reanis*

    During a department meeting while we we standing in an echo-y space, I internalized an earth-shattering burp. To my horror, this did not muffle the sound. I furiously tried not to blush as my co-workers slowly deduced it must have been me (a relatively small woman). And I had a serious urge to whistle nonchalantly like a cartoon character.

    1. The Photographer's Husband*

      Hey, you’re not alone. My wife (also a relatively small woman) out-belches me (a somewhat large male) in both frequency and volume on the regular. She then calls out any humble belching I attempt as ‘gross’.

  84. PugLife*

    I had a phone interview a few months ago that was….. okay. There were two people on the other end and I’m not great on the phone to begin with. There was a lot of stopping and starting and talking over and “oh no, what were you saying? go ahead”. Plus it was a seriously last minute interview – I heard about it from a friend, applied, got a call THAT DAY for an interview the next – so I was not especially prepared.

    I ended this fairly awkward interview by saying “So, I can’t quite tell… are you offering me this job?”

    In my defense the interviewer’s verb tense was very much “these are the things you’ll be doing, we’ll want to talk next week about XYZ project…” which I realize is easier than saying “the person in this job will” but UGH.

    I got the job but it took a few days before the feeling of “oh god I want to die how could I have said that” went away.

  85. Squirrel!*

    A co-worker at my previous job was really weird–she would loudly talk to herself (like, full conversations where she would be two people talking), yell at her phone for ringing, yell at her computer and strike it; just a lot of general awkwardness. But the time that takes the cake is when she got so upset with herself for doing something wrong (no one knew what it ended up being), that she started slapping herself in the face, loudly and repeatedly. And we were in an open office. And we were all sitting in a 15-foot radius around her. She probably slapped herself a good dozen times, then went back to work. No one said a word.

    1. Squirrel*

      And a personal story I just remembered after reading someone else’s similar story: I tripped and fell over a camera cable at a company-wide meeting (I was unhurt though). I’m talking literally every single person in the company was there, they had even bused people in from a satellite office in a city an hour away to make sure everyone was there for it. Not only that, but I fell down *in front* of another camera. And I was holding a plate of food, which went everywhere and some people got hit by it. A very nice woman came over towards me to help, but all she did was pick up the food I dropped, put it on the plate, and then hand the plate to me as I was trying to get up off of my knees.

  86. Kitkat*

    Not sure if this counts, but several years ago I was having a coworker over to dinner for the first time, and wanting to impress her, I decided to make some deep fried plantains, also for the first time. When she texted me to let me know she was about to arrive, I was obliged to text her back that I had overheated some oil, set fire to my kitchen, and forced my entire apartment building to evacuate. Then one of the firetrucks broke down and that shut down the whole block for several hours. Since I couldn’t get to my car, my coworker took me to Walmart to get cleaning supplies, air freshener, and wine, which we then drank together in my smoky apartment when we could finally get back in. It actually totally bonded us and she is now one of my best friends, but at the time I was completely humiliated.

  87. LemonLime*

    I think I told this story here once, but the most awkward work moment I had was a job I only lasted in for a single day.
    It was advertised as an office assistant for a guy who worked out of his home. I expected to help with paperwork and such, but my first day he set me a bunch of personal tasks, like folding his laundry, scrubbing his toilet, ironing his shirts, and making his lunch. The moment I knew I couldn’t handle this anymore was when we sat down to lunch (the one I had cooked) and he reached for my hand to hold as he said grace. I was so taken aback I let him hold my hand for a good 30 seconds as he prayed.
    That night after I got home I emailed him that the job “wasn’t a good fit” and I never went back.

  88. Dealtwiththis*

    I still cringe about the time that I hugged my CEO. I was hosting my first big work event and he showed up to support me. For some reason, I was so relieved that the event was going well that I finally felt like I could let my guard down and was happy that he was there to support me that I just….hugged him. Ugh. I hope he has forgotten about it.

  89. Sunnyside*

    I’m a college admissions counselor and I mostly work with high school seniors. My office has a desk, but there’s also a small table with a few chairs so that I can have meetings with families. My desk chair is the hydraulic kind on wheels that also tilts back. One day, I was wearing a brand new skirt for the first time to work. I had an appointment with a student, a young man who was probably 17 years old, and he was there without his parents. I brought him into my office and I sat in my desk chair and then rolled over to the meeting table, and as usual the chair dipped back a bit. No problem, just zoomed and readjusted. For the rest of the meeting, the student was very distracted. He had a hard time keeping eye contact, I had to repeat questions, he kept losing his train of thought. This isn’t that unusual – these sorts of meetings are often the first time that a student has to engage as an adult, so I just plunged on ahead. I wrapped up the meeting and walked the kid out , then came back to my office and saw a single OB Tampon laying on the ground. It had fallen out of my shallow skirt pocket when I tilted back! Poor kid was sooo embarrassed! And what I thought was an inability to make eye contact was actually him repeatedly looking at the tampon sitting in the middle of the floor!

  90. A Bag of Jedi Mind Tricks*

    At OldJob, my co-worker showed us an email he’d received from the Wife of another employee that he counseled. Seems the email was clearly meant for her husband as she went into GREAT detail about their wonderful, romantic, night before. Ha. my co-worker responded with a “Um, I don’t think you meant to send this to me”. The wife wrote back, “Oops”. That was pretty Awkward.

    1. JB (not in Houston)*

      Once at one of my old jobs, somehow a coworker’s long email exchange with her boyfriend along these lines got sent to the entire company. Out of sympathy and secondhand embarrassment, I did not read them, but a LOT of people did. I felt so bad for her, and I always wondered how it happened because for the life of me, I cannot figure out how you can try to reply to an email and accidentally email the entire company instead.

      1. Not a Morning Person*

        Not me but a coworker: Her husband emailed her an appointment for her Outlook calendar for a date to have some “fun times” at home. He was apparently both funnier and more graphic in his description. He didn’t make it “private” and since we have shared calendars, many staff saw this on her calendar before she noticed and made it private!

  91. a story I tell all the time*

    At my old job, we had a small “New York deli” cafeteria on the campus, Mikey’s, run by a sweet guy, Mikey. I ordered a bagel, as Mikey handed me that bagel, he said, “Enjoy your bagel!”

    I accidentally said “You too!” in response. This didn’t bother me–I was feeling jolly–and I decided to play it off with a little joke. So I added, “Haha, I mean, you can’t enjoy MY bagel…”

    Unfortunately, it wasn’t a real polished bit, and I tend to mumble. So as if my bad joke wasn’t bad enough, Mikey said, “What? ….Oh, you were talking to your bagel.”

    I left immediately and never returned.

    1. Murphy*

      My husband worked at a movie theatre and said when he would tell people to enjoy their movie people would constantly respond with “You too!”

      1. a story I tell all the time*

        Oh yeah, I do it all the time and it doesn’t embarrass me…I just shouldn’t have doubled down :D

    2. DecorativeCacti*

      Reminds me of the time I got to the ticket counter of a movie theater and when they asked what I was there to see, I said, “A movie!”

      1. smokey*

        DecorativeCacti, no offense to anyone else but for some reason this made me laugh the hardest out of anything submitted so far!

  92. Looselips*

    I was leading a meeting to plan a museum opening, and I was successfully suppressing my annoyance with everyone in the room. Until I referred to the ribbon-cutting as a ribbon-cunting. Ten years later I still avoid that phrase!

  93. Bolistoli*

    My old boss was leaving “by agreement” (fired), and we were having an awkward going away lunch for her. At the lunch, in front of soon-to-be old boss (and everyone else at the table within earshot), the big boss and her “favourite” employee joked about how tough it was going to be for “favourite” to do all her work AND do everything she needed to do to prepare and interview for soon-to-be old boss’s job! It was horribly awkward, unprofessional, and frankly, disgusting. “Favourite” is now my boss. We had quite the horrible clique in those days.

  94. JoAnna*

    The most awkward moment I probably had at work was the day I told my (now former) boss in a private meeting that I was expecting my fifth child, and he blurted out, “I’m going to buy you a box of condoms!”

    I just said something like, “We wouldn’t use them anyway,” because ew, dude, none of your business what my husband and I use for family planning. And I think he realized how inappropriate that was because he quickly congratulated me and then changed the subject.

    Second runner-up is the time that company’s controller, who was acting HR (and terrible at it) since the company hadn’t yet hired an actual HR person, ushered the entire company (maybe 40 of us) into a conference room. Apparently what had prompted this meeting was that an employee had been caught watching YouTube videos during work hours (as far as I know, they were innocent ones — work-appropriate, although not work-related) and had been fired as a consequence.

    She proceeded to literally shriek at us at the top of her lungs about how terrible it was to use company computers for personal use, and if anyone was caught doing so they’d be fired immediately, etc. She screamed at us for about 10 minutes while we all just stood there awkwardly.

  95. k m*

    A temp colleague at my first gig out of school had to be sat down by the temp agency and told to wear deodorant. That means the managers noticed and routed to them to deal with… I guess that’s easier than dealing with it yourself!

  96. Errrrin*

    There are so MANY, but a recent goof was when I was describing the collection of resources the library had about Haitian history and instead of saying “Hurricanes and Earthquakes” I said “Hurriquakes.” I then started laughing but the student just stared at me. ¯\_(ツ)_/¯

  97. Seal*

    At my first full-time job many years ago, one of our part-time employees had put in his notice. He came in on his last day with a long piece of crumpled toilet paper hanging out of the back of his pants like a tail. Apparently everyone was so embarrassed on his behalf that no one would make eye contact with him or anyone else in the office. No one, including me, was able to muster up the courage to tell him discretely that he might want to check his pants. Much to everyone’s relief, a few hours into his shift he finally went to the bathroom and came back sans toilet paper. Despite the fact that it was a bit of a gossipy office, no one ever spoke of that particular incident – it was so awkward that it never became part of the office lore.

  98. Snowglobe*

    I was about two more NYU’s pregnant with my second child, and I hadn’t yet told anyone at work. I was a little self-conscious that with this second pregnancy my stomach seemed to pop right out; it seemed noticeable—to me. I was wearing a new dress, not a maternity dress, but with an empire waistline. A manager from another department saw me in the hall and said “New dress? Cute!” My immediate response was “Thanks, I’m pregnant!” In my head that made sense, but I’m sure she was wondering why I made such an announcement at that time.

  99. rubyrose*

    It’s a tossup.
    1. I had been working third shift for several days, covering for someone. My manager and I had a meeting in the morning with a potential client. I fell asleep in the meeting.

    2. Interview for which I was flown in. I took my jacket off because it was warm. Did not realize until after the interview (which included a tour of the facility) that my blouse, while lined in the front, was not lined in the back. I went through the entire interview with a sheer blouse back showing. Did not get the job.

  100. Lucky*

    Well, there was the time I was setting up files for my judge’s afternoon jail calendar – bail and other hearings conducted via video link to the jail – and heard someone clearing their throat, looked up and realized the camera was on and I was broadcasting to the jail AND that the video camera had just been pointing down my blouse. Yep, I pretty much flashed a room of 30+ inmates.

    And

  101. Aleta*

    I’m actually glad to say I don’t have any terribly awkward stories, but closest was back when I was a bike courier. I had just started using clipless pedals (so where there’s a cleat on your shoe and it attaches to the pedal via a spring mechanism), and hand managed to remember to clip out at every traffic light on my way into work. Until I rolled up to my store, try to dismount, and forget to clip out. I fell over and collided with my coworker’s bike propped up against the side of the floor to ceiling front window, knocking that down to! Both our bikes were fine, and I only had the bruised pride of my first Stupid Clipless Fall right in view of all my coworkers.

    1. Kate*

      Oh man. I did something so similar to this last summer. I had actually clipped out with one foot, but then ended up falling to the other side at a crosswalk with a huge line of cars on either side and a restaurant across the street where a lot of cyclists would stop to grab a drink, so basically in sight of the maximum amount of people allowed in that location. I’m pretty sure the next four cars to drive through the crosswalk first stopped to ask me if I was OK. I had been using clipless pedals for like 5 years at that point and hadn’t fallen since the first week I got them, so my ego was mightily bruised (along with my body). I like to think of it as the time the pedals needed to remind me whose boss.

  102. Dylan Is A Lady*

    I’m a comic book artist who does corporate consulting and design on the side and use to temp in medical clinics. So I’ve manned convention tables at regional comic book shows AND led 8-hour meetings in C-suite conference rooms AND checked people in for their appointment about their persistent anal leakage. This means I’ve seen a…very broad awkwardness spectrum.

    My favorite, though, still has to do with one fact: I’m a woman, but my first name is usually read as male. At comic conventions, I stand behind a table full of my work, in front of a banner with my name on it, with a nametag on…but some people still fail to make the connection that I might be the artist. The patriarchy harms us all, etc.

    Thus I had the pleasure of standing behind my table, listening to two dudes pore over all my work and discuss it in brutally honest detail, not two feet away from me. I was obviously just the booth bunny, right?

    It paid off, however, when one of them finally decided to purchase a book…and I cheerfully offered to sign it for him.

    >:)

    1. justsomeone*

      I read your comic!

      I also have a name that people assume is attached to a man and have experienced similar cases of being discussed by strangers to my face.

      1. Dylan Is A Lady*

        Haha, I’m sure you have bucketloads of awkward name/gender anecdotes, too! I wouldn’t change it, honestly. It’s free entertainment.

    2. kible*

      i’ve heard that type of story from like…every woman that does comics, never stops being cringe or hilarious. i tabled my first con last year and luckily didn’t have it (or the dreaded “oh did YOU draw this?”) happen to me!

  103. RJGM*

    I’m just awkward in general, so I don’t have a specific story of my own, but I’d like to submit one I witnessed for consideration:

    My husband showed up to work one day in a suit. We work together (I know), but I wasn’t dressed up that day. As we were walking down the hall together, we ran into my grandboss; she looked him up and down, then asked, “Do you have a job interview today?”

    “Nope, a funeral.”

    I will never, ever forget the look on her face as she started apologizing.

    (It wasn’t super funny at the time because, you know, funeral. But it definitely qualifies as “awkward,” and we laugh about it now.)

    1. eternal teapot*

      Oh this just reminded me of one from middle school (I guess it counts as the teacher’s work). He was a very casual teacher and dresser. One day he’d dressed up for conferences or something. In any case, it was very noticeable. A kid in front of me cracked “Who died?” at him, and very sadly, without missing a beat he said “My mother.” Kid was horrified.

  104. PB*

    Oh, goodness. I was in a meeting once, and a coworker started showing us pictures of her new puppy. We were all cooing over the cute puppy, and she told us how happy she was.

    And then she continued, saying: “but it’s you people with kids who are the real lucky ones. I couldn’t have kids. I had cancer, instead, so now I have to have dogs.”

    1. PB*

      And as awkward as this would be been anywhere in the office, yes, it was during a meeting, with our whole department. It clearly did not occur to the person making the comment that this isn’t the kind of thing you throw in among travel reports and workflow talks.

  105. GigglyPuff*

    First day of my first job at a dog kennel. The garbage bin in the outside yard needed to be emptied at the end of every shift, and during the busy summer season can get quite full and smelly. Well the only way to get it out of the yard was to sling it over the six foot privacy fence to land next to the dumpster. I go to sling it, it catches on the fence top and completely pulls one of the fence slats off.
    I was completely mortified, went through the building and all my coworkers are waiting to have the shift change meeting in the front with my manager, I confess what happened, completely red and embarrassed that I just damaged company property. Once they realized the bag didn’t split and they didn’t have to help me clean up dog poo, they couldn’t stop laughing. Not the biggest deal but I was a shy kid, so it’s always stuck out to me.
    Unfortunately it wasn’t until a few years later when one employee was hurt trying to sling it over that they finally cut a hole in the fence with a latch door.

  106. Still laughing at this one*

    Mine is short but sweet. A while back we had a huge visit from our friends up in the C levels. One of my coworkers asked a VP if they had met before…at the county lock up…In front of our CEO. Our boss looked like he was torn between strangling him or just crawling into a dark dark hole to die.

  107. Sara*

    I once went to lunch with my brother while he was temping at my office. There was one of those quick summer storms just as we pulled back into the parking lot, so we hung out in the car while it passed and listened to the radio. Somehow, I forgot to take my keys out so the radio/battery was on for the rest of the day.

    When I left at five, the car was dead and my brother was gone for the day already. I went back inside for some reason to call AAA because my cell phone was dead and my boss told me he had jumper cables in his car so he could jump it. I went back outside to open the hood and managed to lock my keys into the car before he got outside. He then waited while I went back into the office to try to call my brother or parents to pick me up, but no one was answering their phones so he drove me to their house to wait for them to help me (they lived like ten minutes away opposed to my 30 minute commute). So embarrassing. One of my directors came out during the keys locked in the car segment and laughed for a good five minutes. Took a while to live that one down.

    As a follow up, my mom then tried to jump my car but she had a small coupe and it wouldn’t give enough power. We ended up calling AAA after all that, and they showed up like another hour later.

  108. Where's the Le-Toose?*

    All the Europeans out there will love this!

    My now wife was born and raised in Ireland while I was born and raised in California. I had no idea that in Ireland, “fanny” was a euphemism for vajayjay. I thought everyone would understand it was the American euphemism for butt.

    My wife and I were on our third date and said to come over to her place and she’ll cook me dinner. As she’s at the stove I come up all playful behind her, tap her in the rear, and whisper “I’m going to slap your fanny so hard later on!”

    Her head pivots around like Linda Blair in the Exorcist. She has this look on her face like I’m some sort of super creeper, and she blurts out “what the F did you just say?!?”

    We’re celebrating our 5th anniversary this year. To this day this is still my mother-in-law’s favorite story.

    1. Borne*

      Actually, it’s not just Europeans. Only in North America is ‘fanny’ a euphemism for butt.

      In all other countries where English is spoken, it means the other, i.e. in Australia, New Zealand, South Africa etc.

  109. Liz2*

    We have safety drills for on site shooters where we are supposed to hide in specific rooms. I always pick the bathroom because it’s close and convenient. The last drill I went in and the head of my department head was coming out, I had to tell her we were in a drill and expected to stay for 15 minutes. I had never even been in a meeting with this person before.

    That was the longest 15 minutes of my life- I was a lowly admin stuck in a small space with the head of my department. I made attempts of small talk but quickly ran out of things and she didn’t pick up the ball! After 15 agonizing minutes, I was finally free to escape.

  110. with a twist*

    I was interviewing an older gentleman and he cried during our interview….twice. It was so awkward that I had no idea what to do, so I just froze. His nose was running profusely, so I eventually got it together enough to find him some tissues, but I was completely unsure how to proceed after that.

    During the same round of interviews for that position, another candidate told me about his recent battle with prostate cancer. And of course after that, all I could think about was his prostate and everything else happening in that region, which made things extremely weird. I ended up hiring him anyway because he was a good candidate, and one time he called in sick because his erectile dysfunction medication gave him a migraine the next day. You could have just said you had a headache, man. TMI.

  111. Kalkin*

    This will be nothing compared to a lot of stories, but a few weeks ago, I was in a meeting for a special “mentoring circle” program my company started. We were answering an icebreaker question: Who is your favorite fictional villain? And this poor guy — oh, it’s cliched, but yep, he was a programmer — launches into a brief paean to a character from a series of Dungeons & Dragons novels. And sure, fantasy and science fiction are far more mainstream these days, but this was not Lord of the Rings or Star Wars or X-Men — this was a relative deep cut, and quite clearly very nerdy. And suddenly it just felt like middle school: You could sense everyone’s embarrassment as he mentioned assassins and dark elves, and even though I knew exactly what he was talking about — OH YOU BET I DID — all I wanted was to avoid eye contact with him and distance myself from him as much as possible, lest the attractive women in the room realize I was a big dork too. It wasn’t intentional; it was just like a reflex from sixth grade kicked in! I honestly had never expected to feel that particular kind of awkwardness again.

    (I said my favorite villain was Doctor Doom, because he has diplomatic immunity and frequently makes proclamations about himself in the third person.)

    1. Kalkin*

      Oh! My first job was hosting at a pizza place. This woman walked up to the host stand and said, “Can you call me a taxi?” And I put on my best Bert and Ernie face and replied, “Sure! You’re a taxi!”

      She looked at me in confusion for a couple of seconds and then said, “I’m sorry — I’m deaf. Can you call me a taxi?”

          1. Elim Garak*

            Hah! I was going to ask if it was Artemis Entreri.

            I know he’s not as mainstream as Tolkien, but RA Salvatore isn’t exactly a niche fantasy author.

            1. Kalkin*

              He’s not, but he’s still outside the mainstream. Fantasy readership is pretty small, I think? When you don’t count Tolkien and the few others who’ve made it to film or TV (C.S. Lewis, George Martin, Ursula Le Guin, and that’s about it for high fantasy, right?), the fraction of the population that browses the swords-and-dragons section is low compared to other genres, IIRC.

              Someone must be working on an Icewind Dale cable series, right? They should do it, but make Bruenor a lady to improve the gender ratio. Bruenora Battlehammer.

        1. Elim Garak*

          Not a work story but tangentially related and still awkward. I used to volunteer in the RPG industry and went to Gen Con every year as part of my work. The first time I met Ed Greenwood (in a group) he got down on one knee and kissed my hand. Sweet man, but the whole experience was very awkward.

  112. Kalkin'*

    This will be nothing compared to a lot of stories, but a few weeks ago, I was in a meeting for a special “mentoring circle” program my company started. We were answering an icebreaker question: Who is your favorite fictional villain? And this poor guy — oh, it’s cliched, but yep, he was a programmer — launches into a brief paean to a character from a series of Dungeons & Dragons novels. And sure, fantasy and science fiction are far more mainstream these days, but this was not Lord of the Rings or Star Wars or X-Men — this was a relative deep cut, and quite clearly very nerdy. And suddenly it just felt like middle school: You could sense everyone’s embarrassment as he mentioned assassins and dark elves, and even though I knew exactly what he was talking about — OH YOU BET I DID — all I wanted was to avoid eye contact with him and distance myself from him as much as possible, lest the attractive women in the room realize I was a big dork too. It wasn’t intentional; it was just like a reflex from sixth grade kicked in! I honestly had never expected to feel that particular kind of awkwardness again.

    (I said my favorite villain was Doctor Doom, because he has diplomatic immunity and frequently makes proclamations about himself in the third person.)

  113. Birch*

    My most foot-in-mouth moment: I was at a conference, setting up my poster. A woman a bit older than me was setting up next to me, so we started talking about articles we’d read recently and I mentioned one written by “the Janet Smith group” (Janet Smith being the first author), which I’d really found interesting. She replies “Oh I’m Janet Smith, I like the sound of the Janet Smith Group!”

    I should have said Janet Smith and colleagues, but the last author is a big name, she’s an early stage researcher, and I wanted to give Janet credit for the article since the bigwig often gets credit for the whole lab’s work! It just came out so weird, and obviously it was humiliating to have no idea who I was talking to, especially when her name was right up there on her poster!

  114. Katie*

    I was setting up lunch with a female vendor who I’m friendly with on a professional level (I am also female). She graciously had me order something for myself even though I wasn’t part of the meeting which was a nice gesture to an admin. For some reason when she reached for something her hand accidentally grazed my boob, she apologized mortified, “oh my god i’m sorry I didn’t mean to touch your boob”. To which I responded “hey there’s no such thing as a free lunch!” I don’t know why I said that! I’m not mortified as it eased the awkwardness but it was still like why did I say that?!

    Luckily, I had trouble thinking of something which goes to show no one remembers your awkward moments as much as you do!

  115. Anonymousaurus Rex*

    Oh man, this is seriously embarrassing.
    Once, after a dinner/drinks with a client on a business trip, we got talking about some of our most interesting experiences abroad. Someone brought up Thailand, where I lived while doing fieldwork for my PhD. I mentioned some of my experience talking to sex-workers there. Somehow this ended (after a lot of awkward prying from the client that I should have extricated myself from!) with me relating the story of two men having sex on my lap at an “underwater erotica” show in Bangkok. (I am, incidentally, a gay woman). It’s not like I was drunk or anything, I just got wrapped up in telling the story (which was entertaining everyone, but totally inappropriate) and got carried away not thinking about my audience….a 50-something straight, male, ex-military defense contractor. The next day he kept making oblique references to the story. It was SO awkward.

    1. Close Bracket*

      If you are going to ask prying questions about Thai sex workers, you better be prepared for any type of story. :-)

  116. Alisa*

    I was sent to a training to become a water fitness instructor, which at my facility was always led from in the water. At the class, we learned you should properly teach from the side, and because of the height difference of standing on deck vs people in the pool you should always wear shorts. Reason being that no amount of personal grooming “down there” could provide an appropriate view in only a suit. Required materials for class? Swimsuit, towel, notebook. That was a painful rotation of about a dozen of us doing our teaching assignments with not a pair of shorts in sight!

  117. Jadelyn*

    I’ve told this one before in other contexts – namely how great my boss can be about stuff – but it remains my most awkward work moment to date, so I’ll share it here as well.

    It had been a stressful couple of weeks and a bad day on top of it, so at lunchtime I decided to go home and have lunch with my partner (who was home sick that day) just to get out of the office and spend some time with someone I knew was on my side. As I gathered my wallet and keys to leave, I texted my partner: “F*** this place and everyone in it, I’m coming home for lunch, what do you want me to bring?”

    Only I didn’t text it to my partner. I accidentally texted it to my boss.

    But there’s a happy ending here. She came out and caught me in the parking lot before I left, reassured me that she hadn’t read past the first two words because she immediately realized it hadn’t been intended for her, deleted the text while showing me her screen so I would know it was gone, and then gave me a hug and told me to go and not think about work at all for the next hour – and if there was anything I needed to vent about when I got back, to let her know.

  118. 2ManyBugs*

    A handful of years ago, I tore cartilage in my rotator cuff, and had to wear a sling to work for several weeks. I told everyone it happened in the gym, except my hiring manager, who I had a great, close relationship with. Quietly, at a team lunch, I told him it was actually a combination of Jameson and a house party where the host had a dance pole installed for exercise. (And of course, once we all got drinking, everyone decided to take a swing or two around it.)

    Unbeknownst to me, another project manager overheard this confession. After lunch, once everybody had settled into their desks and during a quiet lull, she suddenly popped up from her desk and yelled across the floor, “HEY OP, WHEN ARE YOU GOING TO TELL US HOW YOU BUSTED YOUR SHOULDER ON A STRIPPER POLE?!”

    I’m female. I work in software. It was like watching gophers, all the heads that suddenly shot up from behind their monitors, turned in my direction. I just about disappeared into my chair, and I don’t think I’ll ever fully recover.

      1. 2ManyBugs*

        She was actually very nice, and we’re good friends now! But she had that foot-in-mouth moment where she didn’t think about what she was saying, where she was saying it, or any other context – something she got better about in more recent years. :)

  119. Nepotism*

    This isn’t technically “while working”, but I got my current job through a bit of nepotism. My mom introduced me to a director in a different department at the company where she works, and I was told to apply for position X, which the director in question was interviewing for herself. When I got to the interview, she asked me how I’d heard about the job, which I thought was odd, but I told her through my mom. Then she asked who my mom was, and I realized she didn’t recognize me. As soon as she found out who my mom is, she basically stopped the interview and told me that unless god himself interviewed, I had the job. I felt so awkward for assuming that she’d recognized me from the start, and then for basically only getting the job because the director of my department knows my mom. I’m still at that job, almost a year later, and I still feel bad for the other people who interviewed who would probably have done better in this role but lost out to nepotism.

  120. Meliodas*

    I had just started my new job at a nonprofit and was meeting some of our board members for the first time at an after-hours event. I was involved in a pleasant conversation with 4-5 others toward the end of the evening when one board member raised his hand to wave goodbye. I mistakenly thought he was raising his hand for a high-five (why? I don’t know!!). Instinct took over and I felt myself reaching across the circle with my hand over my head to high-five him. I knew I was mistaken as it was happening and could not stop myself in time. I ended up in the middle of the circle with my hand weirdly pressed against his. He gave me a blank look and turned around to leave. It felt like the whole thing happened in slow motion. This board member and I now have a great relationship, but I have never mentioned our first meeting to him and he hasn’t brought it up either.

  121. Amity*

    Easily the worst one for me: We had a manager, who we all loved, whose husband passed away from lung cancer. Several months after that happened, she called my department looking for my coworker, who was on a smoke break at the time. Guess what I told her? “Oh, he’s not in the office right now, he’s out getting cancer—um, sorry, he’s on break. I’ll have him give you a call.” I was too embarrassed to tell that to anyone for years!

  122. Curly In A Cubicle*

    Oh boy. I’d applied to a reach job internally. I’d spoken with a man in the department who’d encouraged me to apply, and then I got a call from him asking for a meeting. Great! I think.

    I go to his office, and as kindly as possibly, he lets me know how much *more* qualified EVERYONE else who applied for the position was, and that he wanted to let me know because “we’re like a big family at [large educational institution]” and he didn’t want me to get an anonymous letter rejecting me.

    I managed to keep my face neutral and tell him I appreciated his time and caring. Then I left as quickly as I could.

    I would have so much more appreciated the anonymous letter.

  123. Murphy*

    I was working at a nonprofit no-kill animal shelter at the time. I was in animal care, which is part exactly what it sounds like and part customer service by answering questions and helping potential adopters visit with animals. To adopt an animal you have to apply with the adoption staff. This is a different department, and animal care is not privy to all of the rules and procedures that might make the adoption staff approve or deny potential adopters. (We were also generally prevented from asking about it, but that’s another story…)

    The place is really busy on the weekends, so it’s not uncommon for part of a family to be in the visit room with a dog and another part of the family be going through the adoption/paperwork process. I had been helping a couple with a child for a while. They were visiting with a puppy and seemed pretty nice. Eventually, the mom went up to go apply to adopt while the father and son stayed in the room with the dog. They were in there for a while and at one point the mom came back. I poked my head in and asked “Everything going ok?” The mother was crying and the father and child looked upset. She said “They won’t let us have him.” Apparently the adoption staff denied them. At this point, I was in the doorway leaning into the room while trying to make sure this puppy, who was licking my hands, didn’t run out the door. I just said, “Oh.” No one said anything. Since the puppy was already at the door, I think I said something like, “I’ll just take him…” and then took the puppy back to his room.

    I felt so bad for them. I still have no idea why they were denied.

  124. Ann Cognito*

    Working in CA, most jobs have a very casual dress code. One place I worked was no exception. It was super casual, unless you were meeting with clients. People regularly wore shorts (not short-shorts!), even the CEO, who I reported to.

    Soon after I started working there, a client meeting was being held later in the day. Before the client meeting though, there was an all-staff meeting, so almost everyone (approx 50 people) was there. I walked in just as it was about to begin, saw the CEO, who was wearing khaki pants and a nice shirt, did a double-take and said “Wow! it’s the first time I’ve seen you with pants on.” I was mortified when I realized what I’d just said.” Everyone there thought it was hilarious, including the CEO, and I still get reminded of it occasionally when I see some of the co-workers from there that I’m still in touch with.

  125. Sara*

    Oooh…I’m going to have to go with the time I was working as a teaching assistant at a preschool, and while working with one of the kids, I heard a commotion on the other side of the room. I look up to find that the teacher in the room was having a seizure and had begun to remove her clothing. All of the toddlers were running over to me to ask ‘What’s wrong with Ms. N?’. After I quickly moved all the kids to the other room, that was an awkward one to deal with…

  126. engineermommy*

    My department is so full of awkwardness that we have an award for it. Yes, an actual trophy that gets passed to whoever made the most recent inappropriate comment. My first and only win in 4 years or working here was when, during a discussion about how a coworker’s dentist wouldn’t approve of her eating some sticky candy, I helpfully suggested that she didn’t have to chew, but could just suck on it.

    So now the trophy is sitting on my desk, which prompts people to poke their head in and ask what I said to win it, forcing me to relive the moment over and over again.

  127. CV*

    This is not going to be the most awkward thing here, but was certainly distressing to me at the time. As a young professional woman (early 20s) I wore a lot of colourful button up blouses and neutral coloured pants. (Turquoise and dark grey, for example). My boss was a man in his late 40s who had the knack of showing up to work wearing exactly the same colour combinations as I. The only difference was the way the clothes were cut! It happened every few weeks. I didn’t have the money to invest in a new wardrobe, and he thought it was funny that we were “office twins” and pointing it out during meetings, so of course everyone else noticed, too!

    1. CV*

      oh, man, I forgot the other one I witnessed recently.
      My husband and I were test driving cars, and the salesman (whom we had only met about 10 minutes earlier) gets into his spiel… and somehow ends up asking my husband if he’s had a vasectomy. Husband and I ignore the question as though it hadn’t been asked. We did not buy a car from this guy.

    2. Former Admin Turned Project Manager*

      I had a similar thing happen in high school- I was wearing a sunny yellow oversized sweater, and my doofy pre-calculus teacher was wearing the same one (not quite so oversized on him, of course)! I planned to pretend I didn’t notice, but he came over to my desk, pointed at my sleeve and then his own a few times, and gave a big, doofy “check this out” grin. I heard about that from my classmates for months- Hey, K, did you buy any more of Mr. Black’s sweaters at the mall when I saw you shipping this weekend?

  128. oranges & lemons*

    This one was just secondhand, but it’s one of my most treasured memories. I used to work for an old-timey photo studio where people would dress up and have their pictures taken. One of our most popular scenes was the “bathtub scene,” basically just an old clawfoot tub that a couple would sit in together (yes this job was pretty weird on a fundamental level).

    One day, we had an unusually tall and burly customer who wanted to do this scene with his wife. Usually the tub was big enough to conceal customers’ lower halves, so they just needed to change their shirts, but this guy would clearly not fit. So to preserve his modesty, we showed him into the change room so that we could try to find something for him to wear. Since most of our men’s costumes were meant to fit over their clothes, the best we could do was a very short pair of pink, teddy bear-encrusted hot pants. He was a pretty good sport about putting them on, but unbeknownst to him, while he was still changing a massive tour group of about 30 people gathered at the front of the store. Since the change room and the bathtub setup were on opposite ends of the store, they had a completely unobstructed view of this huge tough-looking guy in tiny pink teddy bear shorts shuffling across the length of the store.

  129. Arjay*

    I know I’ve already shared about accidentally slapping my boss in the face that one time.

    And tripping over the dog leash I was using to tether my chair to my desk so people would stop stealing my chair. I had to file an accident report on that one.

    I don’t know if I ever mentioned going in for an interview at my first retail job and slipping on the floor near the shopping carts. I didn’t wipe out completely, but it was definitely a blip. I thought I might have gotten away with it until something like two years later when the assistant manager who interviewed and hired me said, “Hey, remember when you almost fell on your ass when you came in to interview?”

    And most recently, I came back to work after being out for two weeks between PTO and the flu and one of the managers walked up to me while I was talking to someone else and gave me a really awkward side hug while asking if I had a good time. He wasn’t in the loop that I’d been sick. I wasn’t contagious at that point, but it added an extra layer of awkward anyway.

  130. knitcrazybooknut*

    I worked in Human Resources at an insurance company. We had training session each week, where we flew in our newly hired employees to our home office and put them through a full week of training on all of the laws, regulations, training techniques, and everything they needed to know to sell our particular product. They were also sold on the company at the same time, so there was some wining and dining done at the same time.

    Mind you, I was in Payroll at the time, and I had landed in payroll by virtue of temping, being consistently a good employee, and knowing how to do data entry well. I knew nothing about HR. I knew how to solve puzzles and figure out paychecks and explain them to people.

    So everyone else was out of the office when a new sales agent walked in one morning in the middle of the week and had to talk to someone right now, immediately. I looked around, realized I was the only one available, groaned inwardly, and said, I’ll be happy to help you. We went into a conference room, and I realized I could smell the alcohol oozing out of his pores.

    He talked for about 45 minutes. I won’t transcribe the entire saga, or we’d be here all day. But he described in full detail the entire night, in which he and his fellow trainees were treated to dinner, a visit to a winery, and another dinner and drinks back at the hotel by the trainers and a visiting C-level executive the previous night, during which he had imbibed a perfectly REASONABLE amount of alcohol, which he described drink by drink, as if to prove it to me. During this entire explanation, he would not meet my eyes, until he finally said to me, “I am NOT an alcoholic.”

    I’m not a profiler, but I’ve dated some liars in my day, and I’m well aware that people who want to convince you they’re not lying will give you dead on direct eye contact. (Others will usually give you eye contact throughout, generally speaking.) This guy was trying to convince me, and possibly himself. His general odor was not helping his case, either.

    He then continued his story, saying that the hotel staff then 86’d him, saying he could stay, but couldn’t drink anymore. He continued to describe his behavior as perfectly reasonable, in detail. But then one of his fellow trainees set down a half-drunk beer! And said she wasn’t going to drink any more of it! He couldn’t believe it! Well, any reasonable person couldn’t let that go to waste! So he just absent-mindedly picked it up and drank it, of course! You would have done the same!

    The hotel bar staff immediately came over and told him they would be reporting the incident to his company immediately and he needed to leave the bar.

    He came to me and wanted to make sure that the company heard it from him before they called and reported him, so he just wanted to be sure I knew what REALLY happened.

    The entire time I just sat there, nodded and took notes. I had no idea what else to do. I’d give anything to have those notes. I should have made a copy. Ye Gods.

  131. Higher Ed Database Dork*

    Here’s one from early in my working life…my first full-time job out of college, I was hired at a private university to design online courses. My team was in a very small room with an open office plan, so we could all see each others’ computers. On my first day, they gave me access to the stock photo account and instructed me to make some graphics for an online course. One of the graphics was a banner for the test/quiz section. So naturally I think, “I’ll look for pictures of people taking exams,” and typed “exam” into the search bar. What popped up was dozens of photos of topless women giving themselves breast exams. Full exposure, nothing was blurred or creatively hidden. So on my first day, I gave all my new coworkers a big eyeful of boobs getting checked over.

    Thankfully they all just laughed and said the same thing had happened to them, so don’t ever just search for “exam” in the stock photo site!

  132. S*

    Once a senior manager took the whole team out for lunch (about 6-8 people). I was feeling like I wasn’t really participating in the conversation, so I was looking for an opportunity to jump in. Somehow the talk turned to the city of Annapolis, so I chimed in “I gave birth in Annapolis!” There was a *very long* silence, as no one had any response to this. Thankfully, some eventually changed the subject. I didn’t say much for the rest of the meal.

  133. Awkward Pharmacist*

    A mom came up to my pharmacy counseling window to ask for help regulating her son’s bowels. “He didn’t go for twelve days, and then when he finally did go, it was the size of a sweet potato.”

    Shortly after that, I discovered that the son in question was the hulking teenager failing to hide behind her.

    I’ve never been able to look at sweet potatoes the same way again.

  134. FlamingoFlorence*

    I was hosting a retirement party for my boss and I completely forgot to invite one person. It was an oversight, because I had him on the list, but somehow forgot/accidentally deleted his name in the “To” field. He got wind of the party and he said “Hope you have fun at Fergus’s party tonight!” and I said “Oh yeah, we totally will!!”. Then my other co-worker had to tell me, oh, Bill is actually upset at being excluded. *head-desk* I hate feeling excluded and would never intentionally do that to someone, so I was mortified. I invited Bill and I think he believed me that it was unintentional, but I felt awful.

  135. Bill F*ckin' Murray*

    I’m a woman and I work on a small, very tight-knit team. I was sitting at my desk when two co-workers came in to talk, one man, one woman. At a certain point, the woman realized that her pants zipper was inching it’s way down and she kind of pressed at it an laughed. The male coworker, thinking that she said her stomach was growling, exclaimed that that always happened to him in my office! We both just stared at him in shock with our mouths open. Then I yelled, OMG, why would you say that?! He was confused, we were confused, once we figured it all out we laughed until we cried and I’m crying now thinking about it.

  136. Eye of Sauron*

    Am I the only one that suddenly has a flood of awkward memories coming back because of this thread?

    lol… it’s hard not keep adding them!

  137. Pleading Insanity*

    I was once moderating a high-level, invitation-only, think-tank type of meeting. Because it was for a niche industry, most of the participants already knew each other, but I wanted to get everyone talking so I had them introduce themselves and tell me something they didn’t think anyone in the room knew about them. I was calling out names alphabetically and things were going nicely – a good mix of funny, sweet and impressive anecdotes. I got all the way to the Ws and called the first name “Mary White.” We all look around. Mary isn’t there. I move on. “Paul Winter.” Paul isn’t there. I make an off-hand comment, “They must be together.” The room erupts in laughter and I think, “not that funny, but good to know I have an easy crowd.” Later, one of the big shots in the group comes up to me and says, “I can’t believe you said that, but good for you. Someone had to say it.” Turns out they were indeed a couple, and were indeed together – and both married, not to each other. I was apparently the only one in the room who didn’t know that. It’s been years and I’m still cringing.

    1. TheAssistant*

      In a way, they absolutely let you know something you didn’t know about them, even without participating in the icebreaker.

  138. Lily Evans*

    I have so many, but possibly my most awkward story comes from my high school job. I worked at a big box store (like Walmart, but not Walmart) that had a bunch of teenagers working there, so of course everyone was friends and there was an incestuous tangle of inter-company dating and hooking up. Around the time of senior prom, my friend Stassi took it upon herself to find my a prom date, despite me telling her I didn’t want to go, so I didn’t care if I had a date. But Stassi was one of those people who sets her mind on something and doesn’t give up, so she started asking guys out on my behalf. The first time I heard about it, I was super embarrassed because she’d asked a guy I had a crush on, but who already had a girlfriend.

    Then it got worse. Our other friend, Kristen, had just broken up with her boyfriend, Tom, so guess who Stassi asked out on my behalf next? Yes, our best friend’s very recent ex-boyfriend. But the worst part is that I found out about this when Tom called me over the intra-store phones while I was helping a customer, and was like, “So I guess we’re going to prom together.”

    I told him that I couldn’t talk to him right then and hung up. So there I was trying to help a customer with something while processing the fact that Stassi had promised me as a prom date to Kristen’s ex, who I had no interest in. I finished helping with that customer as Kristen started calling me on my cell phone, so I went and hid in a security camera free stock room for like half an hour to talk her down from being angry at me for asking out her ex. I ended up not going to prom in the end, and somehow no managers picked up on any of the drama so it luckily didn’t affect my job, beyond the intense embarrassment I felt.

  139. Kat*

    OK, this story is maybe more strange than awkward. I don’t think I did anything cringe-worthy in the situation, but my former boss should be terribly embarrassed. However, I am certain she is not.

    Former boss asked me one day if I used the mini-fridge in our office. I told her I didn’t use it very often and was not planning to use it that day. She said “Oh good. There’s not a lot of room left because I put the dead cat I found on the side of the road this morning in there. Can you send out an all-staff email that there will be a funeral tomorrow afternoon at 3 in the garden?” I was baffled. She couldn’t have really just told me that she scraped up some roadkill on her way in to work and we were going to stage a funeral for it, could she? The conversation went something like:
    “A funeral for who?”
    “The cat”
    “Your cat died?”
    “No, I just saw this one dead on the road. Its not a cat I know.”
    “You want to bury it here at work?”
    “We need to have a funeral.”
    “Grand-boss is ok with this?
    “Yeah, I do it all the time.”
    “And the cat is in the fridge right now?”
    “Its kind of gross, so don’t go in there if you don’t want to see it.”

    I was just a year out of college and and I’d only been in the job a couple of months and pretty much everything I thought I knew about the working world was shattered in that moment.

      1. Kat*

        I soon learned she had turned part of the company grounds into a graveyard for unknown cats.

        I called in sick every time I knew she had a “funeral” planned. I mean, if you want to do that on your own time I’m cool, but I will not be a part of it.

      1. Kat*

        I did try to warn my coworker (only the 3 of us had access to that area) but he just shrugged and tossed his lunch into the fridge anyway. It was (unsurprisingly) a deeply dysfunctional workplace in so many ways. (Co-workers there loved to start conversations with, “I’m not racist, but…” which never ends anywhere good.)

    1. JKP*

      This is the best story on the whole page. I read it three times and laughed harder each time. I’m imagining someone she forgot to warn just opening the fridge and seeing the dead cat there. Also, did anyone ever use the fridge again after they found out it sometimes held dead animals awaiting proper funeral services?

  140. Not Indiana Jones*

    I have serious problems walking through doors.

    One day, I was leaving the building. The door handle snagged on my backpack strap, and as I walked forward, the stuck strap twirled me around and smacked me into the door. The door recoiled. I backed up to try to figure out what was going on, and the strap pulled the door shut smack in my face.

    I hope nobody saw that.

  141. Serendipity*

    At the end of my first week in my current professional job my manager (man in his late 50s) decided to take me (20s) and my one colleague (man in his 30s) out to lunch at a local waterfront pub called ‘the lucky shag’.

    He had to leave early for a meeting with some VIP clients, and my colleague and I stayed to finish our lunches before walking back to the office.

    As he and I walked in the door my manager looked over and asked ‘so how was the shag you two?’, in front of the VIPs who were still there waiting to meet me.

  142. Clever anonymous name*

    I was recently mortified at the funeral of a former manager/mentor, “Bob.”

    Bob had been in a C-level position and I had been his assistant. I was so grateful to work for him. He was known to be quite challenging, but we worked well together. He had such integrity and was highly respected in his field. He was also a left-lean activist who, while put together, looked the part. Many of Bob’s friends had similar looks – very much as they might have looked in the hippy days of the 60s.

    After Bob retired, I ended up as the EA for the CEO, “Dave,” who was prim-and-proper in ways Bob was not (closely shaved, always in a suit, fairly stern, etc.). I enjoyed working for Dave for about a year before changing careers and leaving the organisation.

    Bob and I stayed in touch after he retired, emailing or calling a few times a year. I ran into Dave a few times, but hadn’t seen him for years.

    Bob recently died after a long fight with cancer. His memorial service filled the hall, with hundreds of people from all walks of his life paying tribute to this great man. There were some former colleagues in their suits, but there were also many of Bob’s hippy-looking activist friends.

    I paid my condolences to Bob’s family, spoke with a few former colleagues whom I recognised, then wandered the hall looking at the displays that had been put up paying tribute to Bob. I’d occasionally chat with one of Bob’s friends who was looking at the same display, sharing memories.

    When I was standing at one display, a man started up a conversation with me. He had long white hair, an unkempt beard, a somewhat scruffy suit – and he also had a large welcoming smile and shining blue eyes. He said hello, we chatted for a while. His voice seemed familiar and I felt I should recognise him as one of Bob’s friends, but I couldn’t quite place him. We shared a few pleasantries, asking what each was up to. Mortifyingly, about five minutes later (!) as our conversation was ending, I realised it was Dave.

    Oh my gosh, I have never been so embarrassed in my life! There was nothing about Dave’s appearance that made me think it was Dave (scruffy appearance! shining eyes! such a large smile!) It was great to see him so happy and content. And yet I remain mortified thinking about it even now.

    1. Reba*

      Once at a funeral visitation I thought I was speaking to my coworker whose parent had died. He looked a little different, was wearing glasses, but I was chalking that up to grief and fatigue, contact lenses etc.

      IT WAS HIS TWIN.

  143. Jukebox Gloworm*

    I am so here for this book.
    I’m sure this is not the most awkward thing that’s ever happened to me, but here goes:
    Once when I was getting off work, my partner and I had an understanding that he would pick me up. I saw a red car that looked a lot like his, and without thinking or really looking at who was driving, I got into it. Yup, wrong car. But to make the best out of an awkward situation, I wordlessly handed him a fortune cookie message that I had just gotten that said “Hugs are life’s rainbows” and stepped out.

    1. Murphy*

      Had to cover my mouth to stifle laughter.

      If I were the guy in the car, I would tell that story to everyone forever.

  144. Sometimes Communist*

    I’d graduated with an MBA. Literally in my MBA class, we had assignments on “elevator pitches” – what to say to the CEO when you’re stuck with him/her in the elevator for 90 seconds, to get her/him to notice you and think you’re great.

    Then my first job after I graduated…. was with a labor union.

    However, as a libertarian (anti-union) friend pointed out…. the president of my labor union was “one of the good ones” who was not overpaid compared to his members’ salaries. So… what happened when I was stuck in the elevator with the (famous) president of the union where I worked and he asked me what I was working on? My mind went blank. Of course. Except for my friend’s statement…. thank goodness I did NOT say, “you know, my anti-union friend thinks you’re not as overpaid as some other union presidents!”

    Instead, my mind went blank, I said almost nothing and I just felt awkward. And took it as a sign that it was time to find a new job!

  145. Aurion*

    At a previous job, one of my duties was to collect all the cheques that come in the mail and deposit them at the bank every day. It involved maybe thirty minutes out of the office round trip and was a nice break mid-afternoon for some fresh air.

    This day, I go to the bank as usual…except when it was my turn at the teller, I…had no cheques. Turns out the large manila envelope I used (to carry the cheques and some paperwork I need to staple the deposit slips to) had a hole worn in the corner edge (i.e. not obvious) and the cheques had fallen out.

    I bolted back to my office in the hopes I’d dropped them in the hall or it’d fallen on my desk. No dice. I swore, apparently loudly enough that one of the partners noticed, and bolted back out. Retraced my steps. No cheques.

    At this point I was walking back to the office panicking and wondering how the eff I’m going to tell this story to the partners (small firm), figuring out how many people I’d have to call to tell them to issue a stop payment on their cheques, and generally catastrophizing about the shambles of my life when I got a call from my coworker. “Hey, you on your cheque run? Any problems?”

    “Yeah, to put it mildly. Wait, how did you–?”

    Turns out some passerby must’ve picked up my cheques right after it slipped out…and turned it in to the bank across the street from the bank I was going to. Some teller was nice enough to look up the company name and find our phone number and call us about the missing cheques. Since I was out (I usually picked up the phone) my coworker got the call.

    Since I was the only person without a business card and thus could not prove my employee status, my coworker had to go, armed with her business card and ID, to pick up the cheques for me. And then give them to me. And then let me go to my cheque run that should’ve happened more than an entire hour ago.

    At this point the entire office (coworker and two partners, again, small place) knew what was going on (and were laughing in good humour). AAM commentariat, my face was effing incandescent for hours.

    This never happened again, I can assure you.

      1. Not a Morning Person*

        And you’re story just helped me realize why so many cash/check bags are canvas cloth or similar!

  146. Squeeble*

    At a former job, one of the managers was famously kind of pompous and full of himself. In his spare time he taught Greek and Latin classes at a nearby divinity school, and that school decided to give him an honorary degree, I guess as a thank-you gesture. Which, good for him, but he would not shut up about it! He brought it up during multiple staff meetings, with a lot of fanfare, and gave us all invitations to the graduation ceremony where he would be getting his honorary degree. We all just sat there being embarrassed for him, a few people mumbled congratulations, and we all laughed about it later.

  147. Anonymous in the South*

    A coworker brought her 3 month old daughter in to “meet” the staff before she officially returned to work. I was holding the baby while mom used the facilities. Our executive director, who never really joined in these “meet the baby” things decided he wanted to hold this baby. Before I had time to slightly extend my arms to transfer the baby, he tried to just scoop it out of my arms. When he did, one of his fingers caught on the underwire of my bra and my breast came out of the cup. He apparently realized what happened because he reached out to pulled the cup back over my breast. It happened so fast – like in the space of 10 seconds are less. We never spoke of it, but I couldn’t look him in the eye for months.

      1. Anonymous in the South*

        I’m almost 45 and this is the most mortifying thing that has ever happened to me. He was just so matter of fact about it, like it was the most natural thing in the world to pull my bra cup back over my breast.

  148. Laura*

    I was teaching an LSAT class, and one of the examples in the textbook was about Snoop Dogg’s “Doggystyle.” It was the first class of a 2-month course, and I was trying to add in some light banter to get everyone more comfortable. I intended to communicate that I was not familiar with that classic Snoop Dogg jam… instead, what came out of my mouth was, “I don’t even know what ‘Doggystyle’ IS!”

  149. Sunshine on a cloudy day*

    I was a receptionist and had to manage phone lines/conference rooms. There were two owners/Managing Partners of the firm. I was told their names and shown their pictures so I’d know to always answer their calls/never interrupt their meetings/treat their guest with extreme hospitality.

    Day 3 on the job. I still haven’t seen either of the two managing partners. I get in the elevator to leave and Partner #1 walks up right as the doors are closing and gets in with me (just him and me in the elevator). He looks at me in confusion (there’s only about 50 people in this office so he didn’t know who I was), then says “Hi, I’m Partner #1”. I responded with “oh I’m aware”. Then my mind blanked out and we rode the elevator in silence to the ground floor. No “I’m Sunshine, the new receptionist” or “Nice to meet you” or anything even remotely polite/congenial/professional.

    I was pretty sure I was going to be let go the next day, but somehow I wasn’t. From then until the time I left, I never knew for sure if he ever figured out who I was or if he ever learned my name.

    1. Sunshine on a cloudy day*

      Runner up is the time in an interview when I answered “How are you at math?” with “Well, I’m really good with a calculator”. To this day I don’t know why that came out of my mouth. I’m actually pretty solid with numbers (in a practical/real world sense – not like advanced theoretical math – but this job just required some reporting involving sales numbers from spreadsheets.)

      I’m a super awkward person. For sure. I’ve finally just sort of accepted it and push on through. My biggest issue is my mind blanking out in very inappropriate socially-geared situations, so I now I just keep a mental list of q’s/safe subjects that I can switch to whenever I put my foot in my mouth. Might be an awkward transition, but it’s better than an awkward silence, and most people tend to role with it if I just switch and brush it off.

  150. Cate*

    I had a former colleague who, at a trade show, went out for a cigarette in a little courtyard which was visble from all sides through floor-to-ceiling windows. There was a strong gust of wind which lifted her skirt. Revealing the fact she didn’t wear knickers under her tights. In full view of the entire restaurant during lunch. To this day I don’t know if she realised we all saw, it was too awkward to ask!

    My own was during an interview, I had a horrendous cold/flu thing, but my recruitment agency had managed to get me an excellent interview so I dressed and drugged myself up and went. The first part was fine, I impressed interviewer and she asked if I had time to meet with the other person making the hiring decision. I said yes, but he wound up taking ages and by the time he arrived the cold medicine was wearing off. Halfway through the interview I had a massive coughing fit and the cough drop I’d tucked under my tongue went projectile across the room at him. I apologised profusely, collected it off the carpet behind him, and carried on. Needless to say I was not surprised when the agency later phoned to tell me I didn’t get the job.

    1. Cate*

      I, too, failed to initially include my email. So, bonus mildly awkward moment: when I was interviewing for my previous role at my current company I also did bellringing (on big church bells in a belltower) and had it listed as one of my hobbies on my CV. I’m quite short and when we got to that section the interviewer asked if I had to stand on a box.

  151. helpme*

    A few months ago there was a lot of office reshuffling at my work, and as the newest employee I got moved fairly often to accommodate new workers who were higher up on the food chain. I was prepping my old office for an incoming manager and had her office key in the front pocket of my shirt (for some reason), which I then forget about as I go about my day.

    Later on, I’m using the restroom and as I bend over to flush, the key falls out of my pocket and INTO THE FLUSHING TOILET! I tried and failed to catch it midair, washed my hands in a numb panic, and rushed back to my own office to panic text my friends to see if there’s any way I can avoid telling my boss that I just flushed a key down the freaking toilet (there was not). As I tried to collect myself, I was vacillating between a sheer, blinding panic and slightly hysterical laughter at this unfortunate situation. I still had no idea how to tell my boss what I did without sounding like a complete idiot.

    I took a quick lunch to clear my head, and who did I run into in the hallway on my way back? My boss. Of course. We had a brief conversation where I was desperately trying to seem normal but internally I was sure she could see how panicked and nervous I was, and I retreat back to my office. The consensus among myself and my friends was that there’s no way out of this without coming clean, especially since the new manager will need a key to get into her office next week, so I try to calm myself and go in to talk to my boss.

    I barely got the words out of my mouth before she burst into laughter and couldn’t stop, tears running down her face and everything. Finally, after a few attempts at collecting herself, she informed me that our admin had 4 extra keys for each office and that my story more than made up for losing one of them. She assured me that I wasn’t in trouble, and I got back to work. She told others in the department and I received a good amount of teasing for the rest of the day, but after that it was mostly forgotten. It’s been a few months since that incident, but I can still remember those panicked hours like it was yesterday.

    1. Emmie*

      You’re not alone! I was visiting a work site with a bunch of new employees. My visitors badge fell off my pants when using the bathroom. Before I could debate whether I should pull this drivers licensed sized badge out of the toilet, the automatic flush turned on and it went down the drain. I am still grateful that there was no need to pull it out of the toilet. I was worried that I’d be known as the bathroom badge lady, but I owned it. I told the receptionist right away, and got a new badge. She said it happens all the time. What a relief!

  152. Madame X*

    When I ran into a former classmate from my graduate program at an event at my alma matter. She was one of the featured speakers for the main event that day. After, the panel discussion and walked up to her to congratulate her on her work. In my awkward attempt to start the conversation, I blurted out “you look so good today; I barely recognized you!” A beat later, I apologized because I realized that my comment came off like a back-handed compliment, which was not at all what I intended! Thankfully, she just laughed it off.

  153. Steve D*

    I fortunately had a coworker who laughed both instances off and understood what an awkward goof I am.
    1) Lesson in Listening: Walking to lunch, I mentioned I was going to get a hoagie. She started talking about something, and unfortunately, my stomach took over and instead of listening to her, I was contemplating what I should get on the hoagie. The perfect dressing occurs to me and I absentmindedly blurt out “I bet it would be really good with some southwest mayo!” She stopped, glared at me in disbelief and asked me to repeat myself. Turns out she was talking about how bad her feet were hurting her and that she might have to have her husband rub them that night, to which I seemingly replied “I bet it would be really good with some southwest mayo!”.
    2) Same co-worker, different day. Sitting at the lunch table, her phone goes off. She apparently had a fresh battery and the highest setting in silent mode, and it shook the table top slightly. Before I could be stopped, I say “I didn’t know they made vibrators that strong!”
    We are no longer co-workers, but we are still very good friends.

  154. Overheard at Dinner Table*

    At a regional training. We all went to dinner and chatted. One woman states that such-and-such-a-week, she will be traveling to Napa.
    Him: Napa? Oh, I love it there! Where are you going? Vinyards? Golf?
    Her: Well, I used to live there, so I’m going back for a funeral.
    Him: Oh…
    Me: <>

    The conversation moved on…

  155. anonymouse*

    This happened at my partner’s company’s holiday party. Let’s say the company owner was named Jeanine. One of Jeanine’s relatives, Paul, who had some kind of role in the company that everyone knew was a sinecure, decided to lead us all in prayer before the meal. I already felt awkward because this company had several hundred employees, not all of whom observed Christmas religiously … then it became clear that Paul also wasn’t completely familiar with the difference between prayers and congratulatory speeches.
    “Oh Lord, we thank You for this Christmas season and the gift of Your Son, Jesus Christ. And we thank You for the blessings we have received this year and ask You to bless us in the coming year. And we also thank You for the meal in which we are about to partake. And we also thank Jeanine for allowing us to share in all of her successes. Amen.”

  156. anon in ny*

    Oooh this happened to me recently – background is that we have multiple offices in different cities and two teams that support different product lines that don’t interact much. The two teams recently had to start collaborating to support a new client so I flew out to meet the client to discuss teapots and ended up introducing myself to a colleague from this other office and who is on the other team but has worked at my company for over a year. It was really embarrassing since the client clearly knew who she was (and she was wearing a visitor tag, too, I just didn’t notice) and I looked like a dummy!

  157. OhNose*

    Story 1: I was walking down the hall at work and a coworker said, “Oh, I think you dropped something.” I look back and a panty liner, folded in half, had fallen out of my pocket.

    Story 2: I pierced my nose and was wearing a simple silver stud in it. I was having some troubles with healing, despite being diligent about cleaning it. One day, I was in an office with 2 coworkers. One of them asked if I got a new nose stud. I said no. He counters that it looks new, are you sure. I again said that I hadn’t. He looked confused. I was also confused. Third coworker said nothing. Later that day, I saw that it had started to bleed a bit and there was a ring of “red” around the silver stud.

    1. Kat*

      This reminds me of when I grabbed a tea bag out of my purse (I’m kind of picky about tea so always carry my own) and headed to the breakroom to make myself a cup only to realize I had grabbed a panty-liner instead. THEY ARE PACKAGED VERY SIMILARLY! I don’t THINK anyone noticed, but could have been a little embarassing.

  158. That Would Be a Good Band Name*

    I used to work at a call center and I hired in as entry level with a group of 25 or so people, that included a husband and wife. We spent 6 weeks in a training room together, so you got to know people. Fast forward a few years and the husband/wife had both quit within the first year, but I had stayed on and was promoted into payroll. The husband was rehired. He stuck his head in my office to say hi and of course I asked how his wife was doing. He blurted out “she’s dead”. I wanted to crawl under my desk! I had no way of knowing but if I could have melted into the floor I would have.

    1. Ramona Flowers*

      Oh god, reminds me of the time I merrily mentioned to someone that the coworker who sits beside me had a rabbit. Nope. Rabbit had just had to be put to sleep. Colleague had been too upset to mention it. I felt so bad.

    2. This Daydreamer*

      I got a lot of people asking how my sister was doing after she suddenly died. It was awkward and painful, but I would have had to carry a sign announcing the news to avoid it. It was just one of those things that happen and I always felt bad for the asker because I knew they probably felt horrible.

      Now, the guy who asked me, on Black Friday, “so, how was Thanksgiving, other than your sister dying”? He can go jump in a lake. So can the coworker who told me to smile about a week later.

  159. Erin*

    I work with (2) 20 somethings. One of the lady’s mother came into her office & started cleaning it for her. It was a sight to see. I was laughing but thinking in my mind, if you continue to do it for her how is she going to learn. Yes, this person still lives at home with her parents. I never told a supervisor.

  160. LJL*

    I have to go with most recent as my awkward moments are uncountable.

    I work remotely, and my supervisor is on another continent. So I see him about once a year face to face.

    AT our most recent meeting, I spilled a full cup of coffee all over the table where we were meeting. Fortunately I only got coffee on me, but I ruined his notebook.Of course, we had to meet for another hour thereafter! Even though he was a great sport, I wanted to crawl under the table.

    1. Elizabeth West*

      Ugh, I did that once at OldExjob when a very hot vendor came in to talk to our marketing guy. He was so good-looking and charming (he had a French accent!) that I just kind of turned into a nervous middle-schooler. I nearly drenched the paperwork they were looking at. Soooo embarrassing.

      Marketing guy must have felt sorry for me, because he didn’t even give me shit about it later like he usually did.

  161. kathyglo*

    I was working as a secretary in an office with a woman whom I liked, but who could also be somewhat overbearing and sarcastic. We had all male supervisors, one of whom (Joe) had just gotten a new hairpiece (important later…). Karen and I sat next to each other.
    No one said anything about Joe’s hairpiece, except for a few compliments. However, he and Karen began arguing one day about something involving her workload. Sitting across from her, I just continued on with my typing and tried to MMOB.
    Joe suddenly rushed out of our area towards the supply closet. He came charging back in with a broom, shoved it in Karen’s face, and yelled at her “Here’s something for you to ride on!!!” Without missing a beat, Karen said, “Oh, I thought it was a brush for your hair.”
    Joe fumed and stalked off. I wanted to bust out laughing but had to keep a straight face. Somewaht awkward, but not sure if a winner…

    1. JB*

      Oh that just reminded me of something that happened over 30 years ago and I still feel bad about it. I was talking to a couple of co-workers and I was teasing one guy about never taking off his hat, and I finally just reached out and grabbed it and HIS HAIR CAME WITH IT! I was just like, oh my god, I’m so sorry, and he left (fortunately he didn’t hold it against me). Who would have expected a guy in his late 20s to be wearing a toupee?!

  162. 2 Cents*

    I was showing the intern something on my giant screen. This intern was known for having a poor sense of personal space (definitely in the “awkward” category, not creepy). I was seated at my desk, and thought intern was either directly behind me or to the right a few paces back. Turns out, he had moved silently just to my left — and much closer than anticipated — because when I went to turn for a paper on my desk, my left hand whacked into … his person, shall we say. He said nothing, but I froze, stuttered something like “let me know if you have any questions,” then proceeded, shellshocked, to describe what happened to my coworkers (on chat) while trying not to giggle out of embarrassment.

  163. SubwayFan*

    I was working on my first major event at my new job in Very Large Corporation and had to manage a vendor relationship over an app we were building. Since the vendor was a new, hip, company, they preferred quick contact via text message rather than emails.

    I was presenting our event promotions on Facebook by sharing my screen to a group, and my husband pinged me on FB chat saying something innocuous, like “Hi Sweetie, I love you.” I tried desperately to close the chat, and managed to fire off a text to my husband saying “Shut up! You’re ruining my presentation!” Except I didn’t text that to my husband. I texted it to the app vendor. Vendor immediately shoots back “Did you just say shut up to me?!?” and there follows a lot of angry stuff while I’m trying to keep composed, finish my Facebook demonstration, and not look bad in front of everyone.

    It took a day or so of groveling and apologizing and explaining to get Vendor to “forgive” me. My husband was ridiculously apologetic about the midday chat on FB, and I have since learned to shut off everything with notifications/chat windows before sharing my screen.

    1. 2 Cents*

      If I was the vendor and got that from someone, I’d be bemused, assuming the person hit the wrong window, not offended.

      1. SubwayFan*

        That’s what I would have thought too? And I specifically explained it wasn’t meant for him too. Let’s just say I’ve never rehired this vendor.

  164. Sara Peterson*

    A few years ago word got around that the supervisor of one of the operations teams was having an affair with one of his direct reports. He was married and she was in a long-term relationship with her live in boyfriend. Rumor had it that they were having sex in the supply closets, and they would definitely go on long lunchtime runs together. Everyone knew yet they both brought their significant others to work events (summer picnics, holiday parties, things like that). It was so awkward. Eventually the supervisor divorced his wife and the day it was final they both quit. He wrote a long message on one of the meeting room white boards about how much he hated the company. They got in a van and drove to Mexico together where apparently they are still living on a farm together.

  165. KJ*

    Oh, man, I thought mine was awkward, but it doesn’t even hold a candle to some of the ones on here!

    Still: one of my employees is a kind of socially awkward guy. He’s nice enough and does a good job, but just skirts the boundaries of understood social interaction so that a lot of interactions with him become awkward. One day I was chatting with him and another employee, who was female. Female employee and I had somehow gotten onto the subject of smoking and were laughing about how ridiculous we looked as teenagers trying to look cool by smoking.

    Out of nowhere, guy employee interrupts, “You smoke?” to me.

    “Yes…”

    “I just think there’s something so sexy about a woman who smokes.”

    Cue awkward silence from me and female employee. We both kind of looked at each other and then moved on with the conversation like it had never happened. He legitimately probably did not mean it, but yeeeeaah. I was a super new manager at the time and had no idea how to respond to that.

    1. KJ*

      Oh! And not me, but I once received a phone call from my brother, who worked downtown at a very prestigious company in our area.

      HIM: What are you up to?
      ME: … I’m at work. Why?
      HIM: Oh. You wouldn’t have time to run by my house and grab something to bring up to me, would you?
      ME: I’ve got a meeting, so no. What happened?

      After an embarrassed pause, he told me that apparently he had bent over wrong and somehow ripped his pants clean open. He had tried calling his wife, but she wasn’t answering, so he had been sitting trapped in his chair for the entire time so no one would see. I felt bad, but I also laughed *a lot*. His wife did eventually pick up her phone, so all’s well that ends well!

  166. Nita*

    I once volunteered as a translator on a student tour abroad. I wasn’t feeling well that day and took a Tylenol for the headache so I could be out and about. Everything went well until at the end of the tour, I had to translate a pretty sad local legend – so I’ve got 15 college kids hanging on my every word, and just when I get to the last line I start sobbing and blubbering, and cannot stop. Ugh. I’m pretty sure it was the Tylenol… just to be on the safe side, I now stay far, far away from it if I have to do any public speaking.

  167. Fake Name for This Specifically.*

    I’m trying to describe this without outing myself too much, so some details have been changed. During installations, I will support people who are often in front of large groups of others. One of my clients was giving a very harsh speech to the group (think like, Mike Gundy’s “I’m a man” speech in regards to correcting a behavior)…but would also be giving me thumbs up signs as he went because he loved the software so much. I kept sinking down in my chair so no one would look at me.

  168. Anon for this*

    An odd overlap of friendships and collegial relationships ended me up naked in a hot tub with my boss (same sex, both hetero).

    We met eyes and kind of shrugged, then agreed later to never speak of it again.

  169. fiverx313*

    Welp, this isn’t the most, probably… that’s a rich field to harvest. But this is the most recent…

    I just started a new job as a receptionist. Last week I passed the head receptionist outside as we were coming back from lunch, and she said ‘Happy Friday!’

    Having already had about 50 mini-conversations about it being Friday with every single person going in and out of my building, my brain just shorted out and I said ‘Tastes good!’

    I have no idea why, and I’m sure she thinks I’m insane now…

    1. BadPlanning*

      I love it!!

      Have you listened to the comedian Brian Regan? He has a bit about using the wrong return phrase. Like mixing up “Take care” and “Good luck” into “Take luck.”

      1. Squeeble*

        Haha, John Mulaney has a similar one about responding to “how are you?” with “nothing much.”

    2. Elemeno P.*

      This is glorious and SO relatable.

      A couple of weeks ago, I was writing an email to two people named Dan. My boss asked me a question, and instead of “yes,” I just said, “Dan.”

      1. Ramona Flowers*

        Not my story but I have a friend who was once sneakily looking at Facebook on work time when her phone rang and caught her by surprise. She picked it up and said: “Hello, Facebook.” (She did not work at Facebook.)

    3. Rebecca in Dallas*

      Once I was on the phone with someone in another department, trying to help them figure out a problem. After they thanked me, I combined “No problem” and “You’re welcome” into “Your problem.”

  170. Jen*

    I was fairly new at the organization at the time, and we were getting an interim CEO to cover for a mat leave. I’d met this man once very briefly. A week or so later I was at our board meeting, and introducing myself to the board members, didn’t recognize him, and introduced myself to him. He shook my hand, and told me that we’d already met. I so wished I could have melted into the floor.

    1. SubwayFan*

      Similar story but the other way round: My team had just been notified of the name of our new Grandboss, Ursula, who I’d never heard of let alone met, and later that week we went out to lunch together at a place close to the office. Other folks from our work were there, and as one group was leaving they stopped to say hi to some of us. There was one lady who I didn’t know but she looked familiar and I swear we’d met at some other thing, and I said, “You know, I’m sorry, I’ve totally forgotten your name,” as we shook hands. She got a funny look on her face, and said, “It’s Ursula.” I also wanted to melt into the floor.

    2. Elemeno P.*

      I am very bad with faces so this happens to me weekly. My life is an endless sea of embarrassment.

      1. Jean Boyer*

        Oh god me too. I have to ask employees over and over what their name is. (I don’t see them often so it takes a long time to sink in.)

        1. Arjay*

          We had a regional manager who insisted on saying “Nice to meet you” to people he’d met dozens of times before. I don’t know why he didn’t just default to “Nice to see you” instead.

        2. Elizabeth West*

          Me too–some I remember right away, and some I don’t. It’s awful because then I worry that the ones whose names I can’t recall think I just can’t be arsed to remember.

  171. AlexandrinaVictoria*

    I was wearing a shirt with sparkles on a dark blue background, that I thought looked like space. Someone complimented me on it and I said “It’s my Star Trek shirt! Where no man has gone before!” Oops.

  172. Bullwinkle*

    Not my workplace, but work related. This took place in a hole-in-the-wall video store in a large west coast city about 10 years ago. I was browsing, a very unkempt dude came in for an interview for a clerk position and I overheard the following exchange:

    Manager: Why do you want to work here?
    Scruffy Dude: To get out of making porn. You have some of my videos. (note: this store had a small porn corner)
    M: Fair enough. If a customer came in looking for X type of movie, what would you recommend?
    SD: (puts head down on counter) Uhhh, ummm, uhhhhh, I don’t know. I’m really tired.
    M: Oh yeah? Been working hard?
    SD: No, I don’t work. I cultivate a lot of spiritual practices, I’m a guru. This is also my first week sober in a long time.
    M: Congratulations.

    The best part was the manager kept a completely straight face and calm voice the entire time, I was so impressed.

    1. Elemeno P.*

      That manager sounds pretty great!

      Somewhat related, an ex of mine worked in a video store in college. His favorite customers were the ones that came in for The Back Corner because they were very polite, in and out of the store quickly, and always returned the items on time.

  173. Dog Lover #1*

    I was part of a college admissions office. During an interview for a new director, the presenter was a single mother of four that only wanted to talk about finding a man, and how hard it was. We all felt uncomfortable, but managed to ask job specific questions. She was ultimately hired. It didn’t turn out well.

  174. CitiGirl*

    The one that springs to mind is the time I woke up extremely late (and honestly, hungover) one morning, and pretty much jumped into my clothes and rushed to work. I made it on time, but I hadn’t a stitch of makeup on (had it in my purse to put on at work), my hair was an unholy bird’s nest mess, and my shirt was untucked. “No problem”, I thought, as I stepped into the elevator full of people, “I’ll just tidy up in the restroom.” While riding up, I felt the unmistakable urge of gas getting ready to escape. The harder I tried to hold it in, the more powerful it became. Without going into detail, let’s just say I lost the battle, in a big way. Thank goodness I didn’t recognize anyone else in the elevator as being from my company. Turns out the crowd in the elevator was a group of potential overseas vendors destined for a meeting with our corporate heads, and all exited the elevator at the same floor as me, noses wrinkled in disgust. By the grace of god, I worked in the most remote area of that floor, and didn’t have to walk by the conference room areas (with glass walls, of course) all that day.

  175. Caitlin*

    The most awkward situation I’ve ever witnessed was a director who was the IT liaison for the department getting into a literal, physical tug-of-war with an IT employee over a printer. It was exactly what you picture, the two of them yanking the printer back and forth going “Yes! No! Yes! No!”. They were in the hallway, and the IT employee was trying to walk away with the printer because it needed to go back to the central equipment repository, or wherever extra printers live, and the director—who wanted the printer for his office—felt entitled to have this in his office as his personal, private printer. The whole thing was stunning. A thing of true beauty. They tugged back and forth on it, voices escalating, while a crowd gathered and stared in mute shock. I don’t even remember how it ended. (It will perhaps not surprise you to know that this was not the first time that Director got into a public scrum in the hallway.)

    1. fiverx313*

      haha that’s amazing… i’d be staring in mute shock, too.

      actually that reminded me of when i was working the front desk at the furniture store, and two salespeople got into a fracas over who a sale belonged to… and it went from a discussion, to a shouting match, to throwing fabric samples at each other, while the rest of us just goggled at them.

      i also don’t remember how it ended…

  176. Amey*

    Ahh, I’ve just thought of one!

    We had an automatic email that went out to our students at a certain point in their contact with us. There were some external delays in this process one year so my colleague edited the email to explain this and say ‘We apologise for any inconvenience caused.’

    English wasn’t her first language so she was maybe slightly less likely to pick up the autocorrect… This email went out for a month until I happened to have a look at it and realised that we’d been apologising to large numbers of students for any ‘incontinence’ caused!

  177. Anonymous for this one*

    Totally cringeworthy.
    We are at a training about reading data points and the presenter (in her sixties, very conservative and formal) switched slides, saying, “Now, guys, THIS is the money shot.”
    I don’t know what was worse–her obliviousness or the fact that three of us promptly burst out laughing.
    We were later called in to discuss how on EARTH we knew what that meant, since, to her horror, she had accessed Urban Dictionary and was clutching-her-pearls-appalled.
    I still laugh about that one.

  178. Kittymommy*

    I had just started a new job (about 1 mth in) where I worked for the heads of the entire organization (think board of directors with primary decision making). They weren’t on that much that 1st month since it was the holidays so I hadn’t had much exposure with them. I hit sick one Thursday night and ended up calling in the following Friday. By Friday afternoon I decided to go to a walk in clinic, w/o then decided to send me to the er (I drive myself). After being checked out at the er, they loaded me full of muscle relaxers and pain killers, resolved the issue, and discharged me. While I was still high of the meds. I go to the parking lot to text my friend to take me home, but instead text the chairman of the board a rambling, incoherent message where the only thing she could understand was that I was at the emergency room, in the parking lot, drugged up, and needed a ride home. At 11 pm. She got back with me about 5 minutes later (she had been asleep), freaking out and asking which hospital so she could come get me. That’s when I realized I had sent the message to the wrong person. My boss (and my friend) tease me about this too this day and I’m still mortified.

  179. Avocado Toast*

    For about 6 years in my late teens/early twenties I got violent PMS symptoms. They didn’t happen every time and weren’t always the same, so there was no predicting it.

    On the second week of a new job, I got hit with them. I couldn’t stand up, was throwing up in the bathroom (and in the hall), was afraid I was going to faint. I knew it would pass within an hour or so but there was nowhere for me to lay down in the office.

    I took public transportation to and from work, but since I couldn’t really walk very well that wasn’t an option…so a coworker who I had met like two days before this happened had to drive me home while I laid in the backseat of her car.

    It was MORTIFYING, has not happened since, and then I had to explain to everyone that it was just PMS and nothing at all serious.

    1. Nita*

      I feel for you! I used to get this too, and one time I almost passed out on a visit to a construction site, in front of my department head, one of the senior VPs, and the client’s attorney. They noticed I wasn’t quite myself when I tried to sit down on a pile of toxic waste. I obviously didn’t feel like explaining what was wrong, and couldn’t think of anything better than claiming I hadn’t had breakfast. In hindsight, that must have made me look very “organized” and “mature”. They were very nice about it, walked me over to a cab… and my boss also insisted on calling an admin to order me a sandwich. Somehow that made the whole thing even more embarrassing.

  180. hhwcid*

    When I worked in backstage theater, I struggled to find black jeans that a) were durable enough to withstand walking/labor/crawling around behind sets and b) fit as snugly as would be ideal. I was sitting on a stool during pre-show one day, and my pants might have been riding a little bit low in the back. One of the performers was walking behind me to get to their dressing room, and as they passed, stuck their finger down the back of my jeans (read: into the crack). They then pulled it out and nonchalantly continued walking.

    There was also the very physically fit performer who pulled down their pants backstage and insisted that we feel how solid their glutes were.

    The most awkward was when we were rehearsing a scene in which a performer picked up a jug and mimed pouring liquid all over herself. Our props person neglected to mention that the interior of the jug had just been painted…and still had wet paint inside. The poor actress ended up getting paint all over her brand new workout clothes.

    1. Dave Wheeler*

      Two Acting stories to add to your’s.
      Take 1) Acting class , doing the scene from “My Cousin Vinny” where Marisa Tomei crawls up the bed towards Joe Pesci. Doing the scene on a pull out couch (I was Playing Vinnie), actress starts crawling up gets to my knees and the couch folds up on us.
      Take 2) Actress starts crawling up we are still having muffled giggles from the first take, she says he lines and I blank, coach yells cut asks what is the problem and all I could do was laugh and say “She won’t quit smiling at me !!!”

  181. GG Two shoes*

    Alright I have a dousy. Each year, our small company allows one employee and a guest to go on a incentive trip with our agents. I was lucky enough to win! hurray! My grandboss, the president, his wife and my husband and I rode at 5:00am to the airport together. Now is a good time to mention how EXTREME on top of and organized I am generally. I really pride myself on that. Anyway, after we get to the airport I realized I left my clutch at home. The one that has my drivers license, passport, tickets, money, EVERYTHING. I’m mortified. My very cool grandboss says, sure take my car back but hurry!

    I drive back as fast as possible and get the clutch. I get back to the airport and… his keyless entry fob is no where to be found. It’s in the car, somewhere. but I CAN NOT FIND IT. My husband is calling me to say I have to get up to the gate right now, everyone else is boarding. I don’t find the fob and thus can’t lock the car doors. I get on the plane and everyone in my group (over half the plane) starts clapping. As I walk to my boss, he asks for his key and I have to say, I don’t have it. It’s somewhere in the vehicle… and then I slink into my seat and die for the rest of the flight/trip…

    Mortified isn’t even close to the feeling I had.

  182. Naptime Enthusiast*

    We had a group pizza lunch and our manager encouraged us to talk about Not Work topics. Our last summer intern was planning to study abroad the next year in a country our manager is very familiar with, so manager asked about the city he was going to, what his friends that had studied there last year recommended, etc… intern started talking about how many people got super drunk every night and came home with lots of STDs.

    Everyone in the room awkwardly pretended not to hear it and talk about how delicious the pizza was for the next 20 minutes.

  183. eating falafel rn*

    When I worked at a restaurant in high school, I answered the phone for a takeout call. The person had a deep voice, so immediately defaulted to addressing them as “sir.” The first time I did it, there was a pause, but then the person continued speaking. I then used the phrase several more times, and I noticed the customer was taking longer to respond each time and something seemed off in their voice, but I couldn’t figure out what, so I just kept on going. Finally, toward the end of the call, I asked if there was anything else I could do for them, and they paused for a long time again, and then asked me, “Do I sound like a man?” I then realized this person was very much a woman. I apologized profusely and said, “No, of course not! I just have a cold, totally my fault.” Then I hung up as quickly as possible and made sure I was not the one to greet her when she came to get her food.

    1. CER*

      My husband also gets misgendered a lot on the phone and I have been guilty of misgendering callers several times myself.. I wish there was a gender neutral version of “sir” or “ma’am” to help in situations like this.

  184. Sami*

    Swearing in front of a class of 8th graders! Yep, I accidentally said “shit”!
    Or having to explain cleavage to said 8th graders— as it pertains to rocks, not the female body.

  185. Sunshine on a cloudy day*

    Runner up is the time in an interview when I answered “How are you at math?” with “Well, I’m really good with a calculator”. To this day I don’t know why that came out of my mouth. I’m actually pretty solid with numbers (in a practical/real world sense – not like advanced theoretical math – but this job just required some reporting involving sales numbers from spreadsheets.)

    I’m a super awkward person. For sure. I’ve finally just sort of accepted it and push on through. My biggest issue is my mind blanking out in very inappropriate socially-geared situations, so I now I just keep a mental list of q’s/safe subjects that I can switch to whenever I put my foot in my mouth. Might be an awkward transition, but it’s better than an awkward silence, and most people tend to role with it if I just switch and brush it off.

  186. TheAssistant*

    In my first company, I was pinch-hitting as an Executive Assistant to an interim VP. We had finally announced the permanent VP, and the interim guy decided to make a little speech to the department (he was prone to speeching). So he’s talking about the new VP, and the department, etc. Then turns to me and says, “[TheAssistant] has been such a great wingman to me these past few months!”

    And I just died, right there. I’m now a ghost.

  187. CER*

    I work in a local government organization, so we spend a lot of time dealing with the public. My former boss was a wonderful person but she was also the queen of conversational awkwardness. One day she was talking to a customer that had just moved into the area. My boss began talking to her about moving and then said “Have you found your toothbrush yet?” The customer looked at her and said, “Excuse Me?” So my boss repeated the question, which led to the customer getting very upset because she thought my boss was insulting her dental hygiene and/or insinuating she had bad breath. My boss tried to explain that whenever she moved she always lost things or had trouble finding her toothbrush in all her boxes and so she was just trying to empathize with the struggles of moving. The customer still left in a bit of a huff and I wanted to sink into the floor in secondary embarrassment.

  188. Morgan*

    I was working at a prestigious business school while I was in undergrad. There was a woman who directed a program that I thought was just the coolest. She had the career path I dreamed of and she was just such an amazing person with an insane amount of knowledge. I was getting close to graduating and knew I would be leaving for my “real job”, and I asked her if she would be willing to grab coffee and chat about her career, etc. I’ve always been a little awkward, but she also made me nervous because I just thought she was SO COOL and inspiring. We chatted in the office, but I was excited to sit down with her 1:1. When we were scheduled to meet, she had to cancel by email due to a last minute meeting, not a big deal. She stopped by my desk a day or so later to apologize and let me know what could work for her to set up another time. As she was walking away, I said…”thanks for touching” with an incredibly long pause..and by the time she was almost definitely out of earshot, managed to say “…base”. My coworker (a good friend before and after the job) and I still laugh about it to this day.

  189. CG*

    I am sure that after I hit “submit”, many, many embarrassing things I have done will come to mind, because I think I embarrass myself with awkwardness (or someone else does it in my general direction) about once a day.

    All I can think of right now is this: my boss regularly mixes metaphors and uses words in not quite the right manner, sometimes to comedic effect. I’m trying to think of a great example, because some of them get into spit-take territory and we have to just soldier on. (Think of the Pushing Daisies episode where Olive says, “I thought masturbating meant chewing your food!”)

  190. Tammy*

    Read another review of this book recently & it’s on my wish list! Why? I’m the person who has to switch tv programs when someone is about to be embarrassed. I just can’t watch.

  191. No name plz*

    My most awkward moment? Okay.
    I live in a condo with no office for package drop-offs, so with my boss’s blessing I had permission to have my occasional Amazon binges delivered at work. Other people did it, too, but I got a little. . .casual. . .about it since the clerk in charge of mail was cool and I didn’t abuse the privilege.
    Well, I had a personal device catch on fire (YES ON FIRE WHILE WE WERE USING IT) and my husband was horrified and asked me to immediately acquire another one since they were quite nice, and we’ll just leave it at that. I double and triple checked on the “discreet packaging” of said item, and it was indeed securely wrapped when it arrived at work.
    In clear packing tape.
    I wanted to move to Mongolia.

  192. The Mango Incident*

    While in college, I worked at my school’s cafe where I was sometimes rotated to the smoothie bar.

    It wasn’t uncommon for some of the smoothie makers to furtively slip some fruit every once in a while. Obviously, it’s not something workers were supposed to do, but it happened (poor, hungry college students and all that).

    Well, this one time, on a particularly slow afternoon, I was feeling pretty audacious and took the LARGEST piece of frozen mango and put the whole thing in my mouth.

    Of course, right after I did that, someone came up to order a smoothie.

    Now this wouldn’t have been such a huge deal if this guy was like most other students: they order a smoothie, then go back to talking to a friend or texting or otherwise don’t interact. Most students may never have noticed the giant piece of mango I was trying to choke down.

    But this guy was not like most students.

    This guy kept trying to make conversation and ask questions. I tried my best to hide my wrongdoing by “mhm”ing through it but I could tell he knew something was up.

    When I was finally able to swallow the last of my guilt, I looked in his eyes and said, way too emphatically, “I am SO sorry, I should NOT have been eating that mango!”

    Awkwardness ensued. He was clearly confused why I was confessing my transgression to him, and so emotional about it. He mumbled something along the lines of, “Uh, that’s ok?”, took his smoothie, and left.

    Every time I saw him on campus after I would feel the embarrassment creep up. I’d wonder, “Does he remember me? Does he think of me as that weird smoothie girl?”

    I worked with him on something else a year or so after the Mango Incident. Fortunately, he didn’t bring it up, nor did I. I can only hope he didn’t remember that I was the same person.

  193. Partly Cloudy*

    In my first post-college job, my boss and her family were all big fans of [Popular Sports Team] and the star player for this team. My boss was pregnant when I started working there and a small group of us were having a conversation with her about baby names. She mentioned that she really liked the name [First Name of Star Athlete] and wanted to name her baby that. I laughed and asked “no, really, what are you going to name him?”

    Silence.
    A look.
    “[First Name of Star Athlete].”

    It’s not even a weird or bad name, it was just not very common at the time, at least not to 21-year-old me….

  194. Faith*

    We had a fairly new coworker and someone had somehow found out when his birthday was and wanted to have a small celebration with cake – comparable to what we did for other coworkers’ birthdays. New coworker said he didn’t want a celebration, and while most of us respected that, that one guy went out and bought him a cake anyway. He brought it and new coworker into the conference room where a group of us were eating lunch, and insisted we all sing happy birthday and eat cake. It was uncomfortable because we all knew the new coworker had specifically asked not to be the center of attention like that, but he was gracious about it.

  195. LAI*

    It was my first week at a new job, and there was an office potluck. I made a dessert. As I was sitting with my new coworkers, one of them took a bite of my dessert, then moved the rest of it to the side of her plate, looked at me, pointed at it, and shook her head slightly, warning me not to get one. I said “Oh, I made those. It’s ok, you don’t have to eat it.” I think we were both mortified.

  196. Looby*

    In my old job I was in a meeting with the Director of our institute, my manager, Gertrude, and the other managers while the director tried to explain how my role would work to everyone. The idea being that while I would report to one manager, the other groups could request my support on their projects as needed.
    The director however felt maybe he wasn’t clear enough and decided he needed an analogy:
    “Think of Looby as a racehorse, while Gertrude is her Owner, the rest of you are jockeys, and if you want to ride Looby you just need to ask the stable owner if the horse is available”
    Everyone kind of sat in silence for a moment, and as the director opened his mouth again the IT manager thankfully said “I’m going to ask you not to say anything more about horses and riding before we have an HR investigation!”
    I got a lot of horse racing emojis from my coworkers as the story got repeated after the meeting…

  197. Alex*

    I was working in a grocery store and the department manager pulled an inappropriate prank on a coworker. Everyone in the department got called into the store manager’s office one by one to tell our side of the story. After that we (including the person who pulled the prank) all had to go back to the department and work while the manager decided what to do. No one was talking or making eye contact. It was unbearably cringeworthy. The department manager got fired later that day.

  198. Legal Beagle*

    My boss kept scheduling and rescheduling a meeting with me, and I was annoyed because she didn’t even tell me what the meeting was about or why it was so urgent that we meet that day. After a few abrupt time changes, I went to a coworker and was venting about how our boss was being so inconsiderate, doesn’t she know I have things to do, she’s messing up my schedule…yeah. Boss had planned a surprise birthday party for me, and the time kept getting moved while she tried to coordinate it so the whole office (a dozen people) could attend. I felt like a huge ingrate, and my poor coworker had to listen to me complaining and pretend to be sympathetic because she didn’t want to ruin the surprise.

      1. winter*

        Agree. We had a surprise event for everyone before the holidays and people weren’t very happy about it because not knowing that it would be ‘free time’, we didn’t get a chance to plan our work accordingly. The idea was nice, but it fell kind of flat.

  199. Chinook*

    My most awkward work moment was on the 2nd day of a 2 day interview in another city. I must have gotten. The time wrong because I went shopping and missed my assigned slot for my teaching audition and showed up an hour late. I was embarrased and apologetic, so the interviewer still saw me at the end of the day but decided to tank it for me by being the worst, most dense student in the one-on-one teaching scenario. Like, literally not understanding any explanation I have on how a certain sentence structure worked. Ironically, my ability to pivot and try 5 different methods to get her to understand the concept won her over and for me the job, but it was the most awkward class I had ever taught.

    1. Chinook*

      And then there was the time my very fit colleague showed up to my classroom after hours to ask for a textbook. He had just finished up a weight workout in the school gym and was on his way home to change (housing was right next to the school) and was still wearing his workout gear where I could see all his muscles. I think lost the ability to speak and he had to repeat the question 3 times before I just nodded, grabbed the book for him and walked over to give it to him.

  200. Jolie*

    Not sure if the most awkward, but quite funny.
    Late afternoon in the office, I’m trying to pull some data out of our big creaky Access database, which keeps losing connection, freezing or otherwise spitting error messages at me.
    Boss comes in and helps herself to the office biscuit box. She makes some comment or another about craving something sweet.
    In a possibly slightly exasperated tone (the bloody database was giving me the “you lost connection” error for the 20th time in 10 minutes), I ask “Does the Internet work for you?”.
    She reacts rather taken aback. She misheard me, and thought I was asking, in a rather judgemental tone “Do you think they’re not bad for you?” (The biscuits, that is).
    I was like : Nooooooo, the in-ter-neeet ! The ruddy database keeps losing connection to the drive! “

  201. Quackeen*

    I was new in a job and heard from a coworker that she was voluntarily leaving the company. I brightly said, “Oh! On to bigger and better things?” She got quiet and told me that, no, she was actually dying of cancer.

    I have learned to just smile and say, “Best wishes to you” whenever someone tells me that they are leaving.

  202. WizzardOzz*

    I pulled up a distribution list at work one time so I can see who was on it – then make a snarky comment about each person on it in an email to a friend. Unfortunately, I left the distribution list on the email when I hit send and sent every single one of them an email with a snarky comment about the others, and about themselves.

    Fun times for the next few weeks at work…

    1. Elizabeth West*

      OMG Burn Book!

      At OldExJob, one time I was snarking about something while on hold and didn’t realize I had hit the page button. Everyone in the entire office and both machine shops heard me.

  203. Victoria Ford*

    I once left a voicemail for my boss in which I signed off with “Love, Victoria.” DOUBLE AWKWARD: I said “love” to my boss, and, uh, I used an email signoff in a voicemail. Whee!

    1. Ramona Flowers*

      You are not alone. You just reminded me of the time I forgot all the ending-a-conversation words like goodbye and eventually, after a long silence, I instead managed to say: “Well, uh, best wishes!”

  204. Foreign Octopus*

    In one of my first office jobs when I was 20, the culture was to eat lunch with your team. Me being me didn’t like that idea. I already had to sit with them throughout the day, and I needed my lunch to decompress and be by myself. Unfortunately, we were in the middle of nowhere. Literally nowhere.

    I went to my car one day but was quickly rumbled. I had to bide my time. Act casual. I integrated myself into the group like a penguin trying to pass as a bird. Head down, all’s good.

    When I’d gained their trust, I stopped attending the lunches. I took my packed lunch (and my book, of course) and I locked myself away in the bathroom – super classy, I know, but I was happy. I had a whole cubicle to myself where, if I positioned myself right, I could even prop my feet up and read happily munching on a sandwich.

    It was heaven for exactly four days. On the fifth, I used a cubicle with a door that didn’t lock properly (I didn’t realise that). There I am, sandwich in mouth, book in hand, and the door swings open and I look up to find my boss staring in at me.

    I manage a smile around my sandwich, looking not at all like I’m about to murder her, and she lets the door go. I hear her heels click as she leaves the bathroom and I contemplated drowning myself in the toilet bowl rather than leaving the bathroom.

    She never mentioned it. I certainly didn’t bring it up, but I could never look her in the eye again.

  205. Cruciatus*

    Oh boy, there have been so many I probably am not thinking of the best ones. The first one that came to mind was when a faculty member, weeks before the new semester came into the office and told me and the other front desk person that she was quitting, she wasn’t being used for her expertise in subject X and it was a hostile work environment created by M (who had just left the office-they had to have passed each other). But me and my coworker were OK and she was pleased to work with us.

    My coworker and I were NOT the ones to handle this. I got up and told my supervisor “Uh, hey, did you know so-and-so was leaving?” and I have never seen her jump out of a chair so fast to try and get more information! And by waiting until the new semester was nearly starting, this person was really trying to mess up the whole system since we had to try to find a replacement ASAP). Oof!

  206. Erika22*

    My team at my nonprofit is mostly women in their early to late thirties, so naturally we had four pregnancies last year. I’m super awkward around babies and baby-related things (and realized that before this time, I had never spent a regular or consistent amount of time around a pregnant woman before? Which is strange but anyway). One of my pregnant coworkers and I were making small talk next to the microwave, and since I wasn’t sure when her baby was due, but didn’t want to ask outright because it seemed rude for some reason, I asked, “When is, you know….” and proceeded to make a swooshing motion with my hands to suggest the baby coming out, all while making a 0_0 face. My coworker took it in stride, but I couldn’t even make my escape immediately because I was waiting for my lunch to finish microwaving!

  207. Buckle Up!*

    When I worked for a kind of a satellite government office, we were expected to keep the office open the day after Thanksgiving, even though the phone never rang, and no one else would really be working. One year, my boss tells everyone that she’ll come in, but we don’t have to and we won’t lose a vacation day. Great, right?

    I was the communications person for the office, and newspapers were still open, and my grandboss wanted a press release sent out on Black Friday about something that had happened at the Capital earlier in the week. She knew no one was really planning on working, but I lived within walking distance of the office, so she asked me to go in anyway to send it out. (I couldn’t send it out from home.)

    Late on Friday morning, I walked over to the office and found the door locked. I was puzzled, but was thinking that maybe Boss went out for just a minute to grab lunch. I used my key to open the door. I even called “hello” when I walked in. There didn’t seem to be anyone there.

    I walked down the hallway, and glanced into my grandboss’ office, to see the NAKED BACK OF MY BOSS while she obviously was straddling someone on my grandboss’ chair!!

    I jumped into my office, and waited for her to come out, since I was sure she must have heard me, but she didn’t. I turned on my computer, sent the press release, and got the hell out of there as fast as I could! As I walked down the stairs, I thought, “Maybe it was her husband, who came into the office for a taboo quickie in the boss’ office.”

    NOPE.

    When I got back to the parking lot, I realized there were only two cars there: my boss and our 19 year old intern! The pieces fell into place, as I had noticed more than a little inappropriate behavior between them, although in my defense, this was such a toxic and unprofessional working environment, and my boss was such a “mean girl” that I think I had become numb to the signs that something really and truly messed up was going on. And because of how awful my boss was to me on a daily basis, I was TERRIFIED that she would know that I knew, and that she would punish me for it. I spent the whole holiday weekend twisted up in knots, and even well after that, since I was already very stressed at that job, and this did NOT help.

    Eventually, she left, and was replaced with someone immeasurably better. The intern eventually became full-time staff, and on my last day, he came into the office, closed the door and said that he had always wondered if I was aware of him and the old boss having an affair. I told him that not only did I know, but that I had witnessed it with my own eyes. He was shocked! It was a nice was to wrap up a truly awkward situation for me (even if no one else was aware that it was awkward).

  208. hermit crab*

    My work involves both public health and public drinking water systems; as a result, there are many opportunities for embarrassment if you accidentally leave the “L” out of a word. The worst was years ago (before my time), when we apparently sent in a major proposal that said “pubic” instead of “public” on the cover.

    1. Nightmare Interview*

      At a previous job I was in charge of designing and printing paper programs for theatrical performances. One time I made a half-sheet for a one-man show that was part of the Best of the Black Box series…

      Performer Name
      *Beast* of the Black Box

      Luckily I caught a few hours before performance and had time to fix it.

      1. Ex-Academic, Future Accountant*

        I’ve heard stories from musicians about publicity posters (pubicity posters?) that left the “i” out of “recital”!

    2. Elizabeth West*

      This happened before I worked there, but a shopping paper published an ad for a woman who was selling an electric organ–the kind that had all the buttons you could push to add beats. The person who wrote the ad put “orgasm.”

      The paper had to run the corrected ad for free until it sold.

  209. MissingArizona*

    Worked at a small store with a counter and people just came up to us to purchase things. Super easy job. My new coworker gets interviewed, and hired at a different location, and transfered to my store. To get behind the counter you just move a flimsy cardboard display and walk back, well this was a big girl, and the space wasn’t big enough. Our counter was bolted to the ground, there was literally no way she could get behind the counter, and she couldn’t go over cause it was glass. I had to call the area manager for the keys to the back door that we never used. I was all of 18, and literally had zero idea what to do or say, so while we waited I just went over stock and protocol. Both of us were awkward, and that just made it more awkward. We did get new protocol with the store keys, and she was a friendly person to work with, so it ended up ok in the end.

  210. Adelyade83*

    I was in highschool and a group of us were going to an all night event for New Years. We had to drive about 3 hours to get there and decided to stop and eat at McDonalds. We also decided to ironically play in the play area thinking it would be funny. We tried to go down the slide train style with all of us holding onto each others feet. During one of the slide turns I turned oddly and my pants split. I had to spend the rest of new years in a long t-shirt trying to be delicate anytime I moved so the rip wouldn’t show.

  211. Tasha*

    Third day back at work after maternity leave, boss asks, “what is that large box you’ve been carrying back and forth” in front of several colleagues. I said, “it’s a breast pump,” kept moving, and he turned bright red. After that I could have walked out with ANYTHING and not been questioned. (This was 20+ years ago, it was a rental, and was much larger than today’s models.)

    1. CG*

      Oh gosh. I worked in an office once where you had to leave your suite to use the bathroom, and one day, my boss (male-dominated field full of socially awkward single men) loudly asked my 30-ish female colleague who was on her way to the bathroom, “why do you always carry your purse with you to the bathroom?!” Her response: “TAMPONS.”

  212. AnnieC*

    This happened only 2 weeks ago. I was mortified.
    Last year I was missed out off of the list calling out the high achievers – over 100% of quota, I also did not get the cube paperweight for hitting target. I was also missed off of the promotions list and it became a running joke throughout the year.
    Come January this year, I’m at the annual awards dinner, sitting with my business unit’s VP and EVP (from my large corporate company) and all the over 100% achievers names are called out and mine is missing again. I felt myself getting upset but thought it was in someway a good idea to say to my VP “This is nonsense, I’ve been forgotten again?! why doesn’t this surprise me. It’s becoming par for the course now. I do well and nobody cares” and he just looked at me and smiled which annoyed me all the more. Imagine my shock when 5 mins later not only was my name called out but I was given a super fancy, all expenses paid trip for 2 to Europe (staying at the Ritz no less).
    I felt awkward and embarrassed every time I saw him for 2 days.

  213. Golden Lioness*

    Oh, my goodness! So much awkwardness, so many funny (now!) moments! =P

    I come from a culture that kisses (sometimes one sometimes both cheeks). When I moved to the US and I finally started my 1st day ever at a US company, as soon as I was introduced to my new co-workers, I went for the kiss. The look of horror on their faces made blush extra red.

  214. Pick Me!*

    I was new in a healthcare-related industry and didn’t know how a particular aspect worked yet. To be fair, it wasn’t described very well. In any case, I misunderstood and thought a direct affect of the issue would cause unsuspecting women to get pregnant. Without wanting to be pregnant.

    I was horrified by this and ended up telling a coworker about it, who agreed it would be terrible to get pregnant unintentionally in this way. To add realness to the discussion, I tried to pull in another coworker, who was within hearing distance, who had just returned from maternity leave, as an example.

    “I can’t imagine being like Tina!” Long pause. “I mean, without wanting to be like Tina.” Pause. “I mean, I know she’s going through stuff and it’s hard…. Sorry Tina. That came out wrong.”

    No surprise I was spoken to by my boss the next day about being kind to others with children.

  215. N.J.*

    I’m a hugger. It’s gotten better over the years, in that I don’t often give hugs to those who don’t want them anymore, but I’ve had some cringeworthy moments. I was temping at one workplace after having worked at a very inappropriate, huggy workplace. I think it became apparent to my boss that I was huggy. I was privately working on toning it down, as I could tell it was making people uncomfortable. She was showing one of the newer interns around and stopped by my desk. Somehow they got into a conversation on hugging or something and my hugginess came up. My boss half jokingly “ordered” me to hug the intern, without knowing whether the intern would have viewed that as a violation of personal space. I cringe to this day, but my brain went into what I can only describe as a combination of hugs are nice/did she really just tell me to do this/what if she is serious?/shock/must obey/people pleaser/no don’t do it/ overload and I hugged the poor intern, who recoiled in horror. My boss then made some sort of snide coment about me really doing that and they left. I have not hugged someone at work since, even if I have to talk myself down, as it were. That poor intern never made eye contact or talked to me again and I don’t blame her. I myself wanted to crawl into a hole and die for several weeks.

    1. winter*

      Okay, but what was your boss going for there? It seems weird that they joke (?)-asked you in the first place.

  216. TCO*

    I was only a few months in to my very first post-college job when one of my coworkers was fired (or at least “counseled out”). He was allowed to leave in a really dignified way, including our customary going-away party and a kind e-mail about him “leaving to grow his own business.” (He didn’t commit serious malfeasance or anything, he just wasn’t effective at his job and even I could see that as a newbie.) I didn’t really pick up on the subtext that he was being fired, so at his party I asked him in front of everyone about his exciting new business venture. It quickly became clear that this “new venture” didn’t really exist.

  217. Kai Jones*

    I was working as a secretary; the office had study-carrel style desks raised on a pedestal with half a dozen steps (so we were all facing the center–and each other–on top of the pedestal). I turned to go down the steps and fell. I was 6 months pregnant and all the other workers rushed to help me get up. I wasn’t hurt and nothing bad happened, but it was incredibly awkward.

  218. Anastasia Beaverhausen*

    I was in my final year of undergrad, and was doing an Independent Study project with one of my professors. He called my apartment one day, and my roommate answered the phone. She thought it was my dad, so told me that’s who it was. So, like a dummy, I picked up the phone very excited to hear from my dad (this was 25 years ago, so no e-mail, cell phones, etc. and I was 4-1/2 hours away, so didn’t get to see or talk to my dad too often). I happily exclaimed “Hi Daddy!” into the phone. Awkward silence on the other end, then…”Uh, I’m looking for Anastasia?” Luckily I recovered quickly and said, “Oh sorry, I’ll go get her!”

  219. TheSoundkeeper*

    A colleague came into my office and sat in my guest chair to ask what I thought was a work-related question but was actually a request to go on a date with him sometime. I was in the middle of answering while blushing wildly, when my manager walked in with an actual work question. Said manager was not known for his appropriateness (once commented “I like seeing my employees on their knees” when watching me sort a lower bookcase shelf), so I bumbled through an answer while willing him to leave quickly and hoping that he was oblivious to the nature of the interaction. 20 years and two children later, I still tease my very intelligent spouse about his approach vs. looking my uncommon name up in a phone directory and calling me at home. :-)

  220. Joielle*

    Once, I was working with a prestigious member of my university’s faculty on a book drive. We were finally ready to launch it and he agreed to send an email to all of his (several hundred) students and contacts to advertise. I got the email a few minutes later and the subject line read, in all caps: “BOOB DRIVE”… followed quickly by a hastily-drafted email apologizing for the error. At least the book drive got a lot of buzz!

  221. Bassoon Wielding Chemist*

    My mother and I were out for a day of shopping. We stopped for lunch at the high-end steak house where I worked at the time and she had been wanting to try. As word got around that we were there various staff came by to meet my mother, very pleasant and uneventful. Then the general manager stops over and this happens:

    Me: Mom this is our general manager, Fergus Smith. Fergus this is my mother, May White.
    General Manager: (extends hand) It is so nice to meet you May, I’ve heard so much about you.
    Mom: (lightly grasps his hand, looks him in the eye) You are a good looking man!
    Me: …

  222. Elemeno P.*

    This will probably out me if any work friends read this blog, but the story is great.

    I work for a theme park. Sometimes we look at what other theme parks do so we can learn from them. A few years ago, my two (male) bosses and I went to a rival park for the day to learn from some stuff they were doing. We walked around, took some pictures, and then decided to go on some rides (why not, while we were there!). It is relevant now to state that I wear dresses to work, and my dress that day had a big, flowy circle skirt.

    The particular ride in this story is now closed, but it used air jets on the ground to make the vehicles float. I figured the jets were only on while the vehicles were in motion.

    I was incorrect.

    My ENTIRE skirt flew up to my head, front and back and sides, fabric billowing all around me. The skirt was pretty voluminous, and I physically could not gather all the fabric quickly enough. I pushed it all down frantically and then sat in a ride vehicle between my two bosses, who I then spent the whole day with.

    My underwear that day wasn’t even cute.

    1. Nita*

      I should have known not to drink coffee while reading here. Now it’s everywhere. Also, hope you didn’t get too many Marilyn Monroe jokes after that…

  223. Liz T*

    Listening to a billionaire fart and pretending it wasn’t happening is probably my most awkward work experience.

    1. Elizabeth West*

      Oh man. I keep from being nervous when meeting bigwigs or celebs by remembering “Everybody poops.” But farts are funny, will always be funny, and I don’t think I could have survived this moment.

  224. Anon for this*

    I’ve told this before here, but for anyone who missed it (and for a chance to win a book!)…

    I was working at a fairly stressful job where we semi-jokingly had asked our boss if we could have an emotional support animal. He said there were people in the office allergic to dogs and cats and for some reason seemed to think we would leave it at that. We did not. Over the course of months we discussed pros and cons of various alternatives including support emus, support goats, and support anything-we-could-think-of (surprisingly emotional support peacocks never came up). One worker even brought up having a snake, knowing that I, his manager, hate snakes to the point where even talking about them makes me cringe.

    So a few weeks later, when we had something really terrible happen, I thought I’d break up the tension by referencing the snake and getting the team to all laugh at me. Unfortunately, what I (20 years older than the rest of the team, sort of straightlaced, sort of respectable, female) very perkily said was “We’re gonna need Worker’s anaconda to get us over this!” There was a moment of dead silence and then an explosion of laughter from everyone present (so…mission accomplished?). My face turned redder it’s ever been and I took myself to hr. That’s when our hr rep lost it and couldn’t stop laughing either. I have a feeling I might still be a legend even though I don’t work there anymore.

  225. Tricksy Hobbit*

    Hi Everyone,

    We suddenly all got an email with a mandatory sexual harassment for the entire business. Of course, our eyebrows went up and our first thought was, “Who did what?”. The harassment training itself was… magnificent, in its own way. Our department was trying our best to keep a straight face when one of the slides had this cheesy video, and the takeaway was a picture on the next slide that said (and I swear I am not making this up): “Don’t get your honey where you get your money.”

    Then the trainer was trying to talk about the dangers of texting and how you can sexually harass over text, and her exact words were, “I know, it’s late, you’ve had a few glasses of wine, so you bang one out” referring to the text. The group in front of us lost it at that point.

    Sexual harassment training: a good thing. Sexual harassment training that apparently came straight out of the 1970s: not so good. To this day, my coworkers and I go into fits of giggles whenever we think of Don’t Get Your Honey Where You Get Your Money

  226. Anonymous for this...*

    Not funny awkward, just sad awkward, or maybe the world’s dullest ghost story.

    I once dated a man in another department of the company I worked for. (This was fine.) Unfortunately, he passed away from complications of medical treatment, and I was devastated. My coworkers were wonderful about it, and a few became closer friends—including one who lived near me and had 4-wheel drive, who told me to call him if I had trouble getting to work in the snow in my hatchback.

    Two years later I was snowed in, but I’d lost the helpful guy’s cell number. I figured I’d call our work number, leave a message and see if he checked his voicemail. At the time, our office had one of those directories where you could spell out the name on the keypad and it would direct to the person’s extension (let’s say the name was “Gaston”). I typed in G-A-S-T-O-N…and got my dead boyfriend’s voicemail, in his own voice (I’ll say his name was “Patterson,” so a lot of letters in common, but not all of them).

    After that, I didn’t feel like going in to work anyway.

  227. Mel*

    One time I was running late to a meeting, cup of coffee in hand. When I opened the conference room door, the meeting had already started, so naturally everyone turned towards the noise. At that exact moment, with our entire group looking at me, I dropped my coffee mug and spilled the whole thing down myself. Including my white shirt. And all over the floor.

    Luckily it wasn’t hot enough to burn me, but I spent some very fun minutes with a bright red face trying to wipe up the coffee from myself and the floor while coworkers brought me paper towels and the presenter awkwardly tried to continue the meeting.

    A close second: one time I was walking down the hallway taking a sip of water. Our VP was walking towards me and said hello. I tried to say hi back mid-sip and, uh, spit water all down my front as he watched. Like that scene in HP and the Goblet of Fire when Harry smiles at Cho and spits juice all over himself. I don’t know why I have such a hard time with beverages…

    1. JB (not in Houston)*

      Once when I’d been called for jury duty, I was sitting in the room with all the other potential jurors waiting to get called to a courtroom. I went to take a sip of coffee but missed my mouth entirely and just poured it down the front of my shirt. Fortunately I had on a cardigan I could button over it, but I couldn’t do anything about the people who saw me noncholantly pour coffee on myself.

  228. Nightmare Interview*

    This happened in my early 20s just before the interview for my first Real Job at a municipal agency.

    While waiting to be seen I used the restroom, but afterward the toilet wouldn’t flush (mechanical; not because of me). I sat there a good minute deciding if I wanted to be the candidate who didn’t flush or the one who broke the toilet. I decided on the latter and was telling the receptionist about the problem when my interviewer walked up and joined the “conversation.” Then she invited me to follow her beyond a counter-height door to the interview area. What I thought was the knob promptly twisted off in my hand; apparently you are supposed to push open. But wait! There’s more! As I’m finishing up a practical exercise, the computer I was using crashed. I just grabbed a notepad and wrote out as much as I could remember doing of this 45-minute project and had to tell them the computer died while I was using it!

    Everyone on the floor – including grandbosses and VIPs were aware of everything and giving me a variety of Looks. Some amused, some incredulous, a few sympathetic.

    As I was leaving they joked that they needed to hire me just so I could work off all the damage. I replied that they’d better prepare for increased insurance premiums. I literally started crying the moment I was alone in my car.

    I ended up getting the position because it was a public-facing PR job and performing so well during an awkward and embarrassing situation actually helped me!

  229. Folklorist*

    I was doing an apprenticeship at a highly, highly prestigious publication. At the same time, I was just out of grad school, but having a weird overlap with still needing to take my grad school exams to complete my degrees, and having a part-time job on top of it because the apprenticeship only paid $10/hr in a very high-cost-of-living city. Basically, I was working or studying 24/7 and miserable and breaking out into stress hives. One day, I had this genius idea–I realized that people (except me because I was always trying to catch up) never went into the office on Saturdays, and they really had all of these fancy couches that never got used, so it would be a great place to study! So I went in wearing my pajamas, set up my piles of study materials, and got to work in a comfy atmosphere (I couldn’t afford coffee shops because, $10/hr, and there was very little room at the tiny house I rented with 3 other people). Except, my stress-hives flared up and were super-itchy. And high on the back of my thighs. Oh, well, I was alone in the office, right? Went into the bathroom, took my pants off, and started rubbing on cortisone cream using the mirror so I could see. And then in walks the photo editor, a pretty high name in the industry. While I’m rubbing my rashy butt. She kind of stammered and walked out and I tried to explain that I thought I was alone and nobody was coming in. She was nice about it, dropped it, and never mentioned it again, but I know that I live in her mind as THAT person (and she probably told everyone else about the kooky apprentice too. Sigh.) Needless to say, I figured out other places to study after that.

  230. Jersey's mom*

    I work for a Fortune 300 Company. I do esoteric environmental work. The Company was planning a multibillion dollar project that had esoteric environmental issues. I was called into a meeting with 25+ Executive VPs, attorneys from two different firms and the VP of the environmental division. My VP was a nice lady, but not overly perceptive. At the start of the meeting, I began to have a hot flash. My skin tone is whiter than snow, and during a hot flash, I get beet red and start (very obviously) sweating from my hair roots to my knees.

    My VP sat next to me and began introductions around the room. Everyone could see me trying to unobtrusively blot the river of sweat off my face. My VP announces my name and turns to me; her eyes grew round, and she shouts out “oh my god, are you OK? Are you sick? Do we need to call an ambulance?”

    I mumbled, “no, I’m just blushing at being in a room with so many VPs and attorneys” and tried very hard to become invisible.

    1. I'll come up with a clever name later.*

      I am fair as well and while I was pregnant with my first born I worked for a medical insurance company. I was in the middle of a training class (as a student) when I suddenly became warm. It was spring, heat was still on, windows closed, pregnant…it was the perfect mix. Apparently I got very red. At times I actually turn kind of purple when I get very red, such is my skin tone. This happened during the class. The trainer immediately stopped the class without a word, went to the phone and called for medical personnel to come to the classroom. The class all kind of looked around wondering what was going on, myself included. Moments later three security/EMT guys come in and she points at me and announces that I am at risk because of my color and pregnancy. The entire class turns which makes me blush harder so I resemble Barney the dinosaur. The EMT’s check me out, talk to me, etc and I tell them I was warm and flush easy. They opened the windows, turned off the heat, and gave me some water. For weeks after my co-workers would say stuff like “don’t make her blush…she can get the officials in here without trying!!”

  231. Not a Morning Person*

    SO many awkward options to choose from!
    At one job where I was a new manager, I had a meeting with my general manager (boss) and a vendor. I had a new blazer and chose to wear it that day. So I’m sitting in the meeting where we are discussing of all things, the William Tell Overture, and I said something silly that made it sound like I thought William Tell was a real historical figure. And the vendor looked at me a little condescendingly and said something like, “You know that is not a real story; it’s a legend.” And I replied, “Oh of course”, and followed it with something about the legend, while gesturing with my hands, and noticing that the blazer still had the extra buttons attached and swinging from one sleeve and that the sleeve also had the white sewn on tag on that sleeve. As a new, youngish manager, I was mortified! Now I can laugh at it, a little, but then I still thought I should try to hide it and I spent the rest of the meeting trying to rip off the little bag with the buttons and unobtrusively tearing off the white tag. Do you think they noticed? Hmm?

  232. ValaMalDoran*

    The husband and wife owners got into a personal screaming match while having lunch in her office. He stormed into the shop, and she followed him. And kept screaming.

  233. Word Nerd*

    I have a problem of excessive mucus. I must clear my throat regularly (eh-hem, or huh-huh-hum, or a voiced cough) or I gag (extended horking sessions). The latter is awful to listen to and experience, so I engage in the former as needed. I try to keep it quiet.. but apparently not quiet enough.

    My office is closest to the front door, where the receptionist/office manager sits. One day at about 3pm she stormed into my office, slammed a bottle of water on my desk, and commanded me, “Stop that disgusting habit! Drink something if you need to clear your throat, because what you’re doing is gross!” I was in the middle of coding at the time, and had not seen her coming, so her verbal explosion hit me like a bomb blast, and I sat there stunned, watching her glare at me as she strode away.

    This is someone with whom I had been on very friendly terms (warm greetings daily, sharing details of family, kids, life experiences etc., including that she fundraised for my kids when they were going on a band trip) and I certainly would have taken even more precautions had I known it was bothering her. This is not the first time she handled things in an odd/inappropriate way (examples include: requiring everyone to stop the common office practice of bringing in baked goods for coffee breaks because she was trying to lose weight: locking up all the silverware because she felt people weren’t taking enough responsibility for dirty dishes) it was just the first time it had been directed at me.

    I waited until end of day when she was gone, and put the bottle back on her desk along with a note. I thanked her for the water, and asked her not to use that tone of voice with me again as I am not a disobedient dog or a mortal enemy to be treated like that. I also explained that it was a medical condition, and said I wished she had told me sooner that it was bothering her, and that I would try to muffle it in the future.

    She did not make eye contact when I came in the next day, nor the rest of that week. For weeks after our communication was limited to a ‘Good Morning’ and nothing further. She has never brought it up or apologized or mentioned it in any way, and I wish she would because I would forgive her. (Who among us hasn’t had a bad day, or snapped when we shouldn’t have?) We are now at the point where there is at least a professional relationship, but any closeness or friendliness is gone, and I am sad for that loss.

    1. Golden Lioness*

      Ugh! I am sorry! I have really bad allergies, and when I have bad flare ups I had people asking my manager to send me home or not entering my office. Most of them are OK after I say I have bad allergies, but there are a few… ugh!

      Its more annoying to me to not be able to breathe!

      Which reminds me of another awkward moment. This one during a meeting with higher ups on my 3rd week on the job. One of the ladies was wearing a strong perfume, so my sinuses immediately closed and my eyes watered. The congestion was bad enough, but in one loud sneeze… (sorry this is gross) I could not get the tissues fast enough. I turned my head fast and grabbed my tissues from my purse, but it was pretty obvious what was happening.

  234. I'll come up with a clever name later.*

    Oh…this one. I still cringe more than 25 years later. It’s not a good story for me, but I did learn from it. I was a teenager at my first job. I was in school, had my first boyfriend, a job, family obligations, friends, and a lot of clubs. I was burning myself out very quickly. My boyfriend’s mom and step dad had just gotten married and were having a reception to which I had been invited. My boyfriend was pretty crappy with communication and time management so didn’t tell me that there was even a party until a week before the date. I knew that I was already scheduled to work and my boss was kind of a line in the sand person when it came to the schedule – “it’s already on the schedule, no you can’t have it off!” – so even asking wasn’t worth it. I decided to call out. BUT…(here’s where it gets awkward!) back in this time before cell phones and texting we would write notes – to friends, to boyfriends, etc. It was the teen thing to do. I wrote my boyfriend a note outlining my plan to get the night off and then….I left it on the counter and forgot to take it with me. The day comes, I call out, I go to the party, life is good. Then I come back to work for my next scheduled shift and my manager pulls me into the office. She then sits there and reads me my own note (sarcastically and with too much glee, but it really was my note so nothing I was able to do). I got a write up. Two weeks later I got mono (glandular fever as it’s known in other countries) and ended up quitting the job outright, but yeah…I still cringe when I remember that.

  235. Mae West*

    On one of his first interviews out of college, my husband sat across the desk of his interviewer. All was going well until husband exhaled too forcefully which caused a noticeable boogey to fly out and land on the interviewer’s desk! He was mortified but he tried to laugh it off hoping the interviewer would find it funny. He didn’t. They stared at each other briefly and the interviewer ended the meeting. No, he did not get hired.

  236. Innocent comment turns tragic*

    I wish it were a funny one, but the most recent awkward moment to come to mind happened just a few weeks ago.

    Sansa had been trying to get pregnant for about 4 years, and finally conceived! We were all super excited for her and very supportive. She had to leave the office for an hour or so for her 12-week checkup appointment. When she came back to the office her desk mate Arya cheerily/cheekily asked with a big smile, “How’d it go?! Still pregnant?!”

    Sansa just said – “No!” and burst into tears. IT. WAS. THE. WORST. :(

    Sansa had actually just found out she miscarried and had come in to let the office manager know in person so she could explain the need for some time off. Arya was obviously horrified at her seemingly innocent friendly follow-up that ended up as a massive faux pas.

    Sansa was given our EAP info and we’ve all been super supportive, but that moment was really awkward in the worst possible way.

  237. Anonymous this time*

    My most embarrassing moment in a workplace came during an interview for my “dream job” right out of college. The company itself was a unique, up-and-coming startup, with a cool office space, progressive work/life policies, and a down-to-earth, casual culture. (Before my in-person interview, the person on the phone told me I could come in slippers if I wanted to. Thankfully, I didn’t.) There was an extremely high level of competition for even entry-level jobs and so I was thrilled when I made it past the phone interview stage and was asked to come to their office for an in-person meeting.

    Everything was going really well right up to the point where they asked me, “What is the hardest thing you’ve ever done?” I then proceeded to tell them about my recent breakup with my fiance, with whom I had been for 4 years, 3 months before our wedding. (Ugh…I’m cringing as I write this.) While I didn’t go into excruciating detail, I remember vividly how instantaneously the atmosphere in the room changed. Needless to say, I was not offered that job. Luckily, I ended up landing in a great place, but I’m still horrified every time I remember that interview.

    1. JB (not in Houston)*

      I just remembered that I once mentioned in an interview at a law firm that I’d found out that morning that my former boss had just been indicted by the SEC. As it was coming out of my mouth, I was telling myself to stop talking, but my mouth kept talking anyway. I knew I wasn’t getting that job.

  238. Taylor Klein*

    Most awkward moment I have ever witnessed at work was while working as a supervisor at a Retail store I was in the process of training in a new team member. This team member had a lady probably close to her 70’s who comes in every week and to buy her weekly supply of cinnamon rolls. She became such a regular that eventually we kept a dozen set aside for her ready to go when she comes in. The new trainee asks the lady if she needs help finding anything or if she is here to pick up her weekly supply of cinnamon rolls. The customer begins to go on a bit of a rant and start explaining how she came in for a “Personal massager” to use on date with some new boyfriend and started to ask her (new employee) questions and recommendations on what she feels and i quote “give me the best experience for my pension”. Never seen an employee go as beat red and ghost white as she did.

  239. Jules*

    There are so many to choose from.

    I was new to the organization and the team was talking about a huge sum of numbers and I was a little surprised. I am used to multiple currency but in my previous work, we are less like to make such an aggressive change to a number. Think of, working in a company with a less than 3,000 employee to an organization with 15,000. I guess it showed on my face when someone helpfully explained, oh, these numbers are in pesos. I knew we were talking in a foreign currency, I just was surprised at the aggressiveness of the change. It would be awkward to explain to her why I was surprised and so I let it go. But it was embarrassing to think that they think I didn’t realize in what currency we were talking about. It was my first senior role too. I felt utterly stupid.

  240. jnsunique*

    I work with someone who manages awkward amazingly well. It’s truly inspiring. He is the highest ranked person at our site and it is one of his tools. A few months ago, he announced in a team morning meeting that his fly zipper broke (and not to look) and we all had a good laugh, because it was of course the day that he had 2 site-wide communications meetings at which he was a presenter and would be standing in front of everyone. He’d already had one of the meetings, and was headed home to change before the next. He uses his mistakes and natural awkwardness to build rapport. There are numerous other examples, but that is such a classic and he handled it so well.

  241. Anna*

    My favorite awkward story!
    When my 2nd daughter was about 3 she had a weird speech problem where she only said the first syllable of any word. So my husband and I decided to take our 2 kids to the zoo. It was just at opening, and the elephant enclosure was the closest to the gate. We saw a crowd gathered and stopped to see why. Found out they were just bringing the elephants out. So my husband puts our oldest on his shoulders, and I put our 2nd on my shoulders so they can see over the crowd. The first elephant comes out and my darling girl at the top of her lungs starts screaming “Whore! Whore! Ma a Whore!” I turned bright red while everyone turned to stare (judgmentally) at me. One of her favorite movies was Horton Hears A Who. I said very pouring “Yes Baby, that’s a Horton”.

    1. Elemeno P.*

      I was so sad when my friends’ kid was able to say his Ls. I’d really enjoyed him pointing out clocks.

  242. Itslikelyn*

    I work in hotels and part of my job is touring people around the property to show them our event space. I was meeting someone for the first time and went to shake her hand hello… but I tripped and smacked her in the crotch (for the record, I am a female so I suppose it could have been slightly worse). She stood very far away from me for the tour… but she did end up signing with us, so at least there’s that.

  243. Bow Ties Are Cool*

    The most awkward scene I’ve witnessed is when a truly incompetent and mansplain-y contractor was literally, physically dragged out by security after being fired, all the while ranting at the top of his lungs about how we were all fools who didn’t deserve his brilliance.

    The following week, the situation took a darker turn when our building was briefly put on lockdown after he threatened to come back and shoot the place up. Then there was a police chase into the next state before he was finally arrested.

  244. nisie*

    I used to work with people with intellectual disabilities and/or autism. So many talks about body fluids and body functions.

    My worst was having a client who needed a shower and taking them to take said shower. Client prepared for shower and then realized he didn’t know how to work the shower. He came out naked and asked for my help.

  245. Symplicite*

    I was newly-wed, new-to-the-workforce (still on probation at my job), and my (then) husband and I were out grocery-shopping one weeknight after work. As we were leaving the store, I happened to run into my then-boss, and was chatting with her. In my naïveté, I had forgotten to introduce my husband to my boss. As the conversation progressed, my husband decided to introduce himself.
    “Hi, I’m . Who the hell are you?”
    Fortunately for me, she had a great sense of humour, and bowled over with laughter. And the next workday, she told me that she’d found it funny, and moved on. Thank God.

    1. Symplicite*