I accidentally sent an email mentioning sex to my girlfriend’s work email account

A reader writes:

I recently sent an email to my girlfriend that mentioned sex.  No pictures, no descriptions.  My exact phrase was “about as much as I hate having sex with you,” which meant not at all.  She did not reply, nor make any comments that warrant such a remark.

I thought this was to her personal email but realized, after had already pressed Send, that it was to her work email.

She works for a huge company, and her job requires her to send about a hundred emails out a day.

What are the chances they flag this? Gets brought to management attention?  Could she get in trouble for something I did?

It is highly, highly unlikely that this will be flagged or that anyone will get in trouble for it. It is Quite Minor as far as inappropriate use of work email goes.

The worst case scenario, which is really unlikely to happen, is that your girlfriend would get a heads-up to stop using work email for personal messages … but again, even that is extremely unlikely to happen. If she’s really worried about it, she could reply with something like, “Please do not email me at my work address,” so that if anyone did happen to look, it would already be on the record that she’s already taken care of it … but really, that’s not even necessary; it’s more of a peace of mind measure.

You should probably take her work email address out of your email program’s auto-fill though, since there are all kinds of possibilities for inappropriate emails to be mistakenly addressed otherwise. And that advice goes for any other mildly risqué emailers out there too!

{ 63 comments… read them below }

  1. Anon*

    That isn’t even the most interesting misuse of work e-mail story I’ve heard this morning . Seems highly minor. (Incidentally, the wife of one of the partners of my law firm has a very similar name to our HR director – apparently, thanks to autofill, he has accidentally sent the later “love notes” more than once. Now THAT is cringeworthy.)

    1. Anon*

      Also, were I IT for a large company, I wouldn’t set “sex” as one of my screening words for e-mail; I’d get back 800 gazillion spam e-mails about sexual harassment seminars, and probably all sorts of completely legit e-mails that tough upon that topic and on things like sex discrimination. And then I’d have to sort through every instance of someone calling a new contract provision “sexy,” and I’d end up never doing anything else.

      1. The IT Manager*

        Way back in the days of the dinosaurs my security guy was setting up alerts for “bad” words in the URLs for the first time. “Ass” was a particularly bad choice. He came in the next days to literally 1000s of warning because the letters are parts of many common words including “class” and a lot of people on the night shifts spent their free time doing schoolwork (Although probably not for online classes. This was in the days of dial up from home before online programs became common.)

  2. Jamie*

    I wouldn’t worry about it. Huge company? They may have key word filters to flag some things – usually to prevent data stealing, although I did hear of a place where the boss had his name flagged so whenever he was mentioned in an email IT had to read it and tell him if people were being “insubordinate” in their email…crazy people…but I digress.

    Even on the slim chance someone sees it any IT who wouldn’t scan that stuff for real issues (legal stuff, and whathaveyou) and ignore stuff like this doesn’t deserve the comfy chair and bank of monitors.

    Just take her work email out of autofill, as Alison mentioned, and put it out of your mind.

    For the record most ITs could not care less about your personal emails and even less about your sex life. Unless it’s funny – and this doesn’t even come close to rising to “you will NOT believe what I read today…” territory.

    Deep breathe – go forth and use work email to flirt no more and you’ll be just fine :)

  3. Not usually Anon*

    Oh – and my name changed to protect the guilty, but if it makes you feel better I bet everyone who’s been working longer than 10 minutes could tell an embarrassing work email story. I have two.

    1. I have a co-worker that has a very similar name to my ex husband. Who I emailed because he was very late on child support…so yeah. Fortunately this co-worker is awesome and has a sense of humor so every so often he still asks if I need a couple of bucks for “our kids.”

    2. Years ago my daughter had been blowing up my email on a very hectic day with nonsense. I had bought the wrong kind of conditioner and I think one of her brother’s ate the Pop-Tarts she bought with her own money and she was busy proposing orphanage and military school options for him. It was summer vacation and she was maybe 13-14 – and her filter between having a thought and needing to email Mom immediately wasn’t working.

    It was one of the most hectic days of my career – important meetings ALL day – and I stopped briefly at my desk on a break to email her to tell her to knock it off and stop blowing up my phone because she was giving me a nervous breakdown and I didn’t care AT ALL that her hair wasn’t as soft as she’d like nor her Pop-Tart deprivation.

    Turns out of the 30 emails from her in my Outlook, there was one from the VP of my most important vendor getting back to me about a very critical question. His email – very similar to my daughters so guess which one I hit “reply” to and send a scathing diatribe about conditioner and Pop-Tarts? Yeah. And I didn’t use her name, so he had no idea why I was demanding he cease and desist with the emails and was probably even more confused about the rest.

    Everyone has their stories.

      1. Not usually Anon*

        He called me and laughed for about 5 minutes before asking me what kind of Pop-Tarts I wanted him to bring to our next meeting.

        He is a very charming (and forgiving) guy.

        FTR – Cherry. He brought them and I did not share them with the little blonde emailing fiend at home.

        1. A Bug!*

          Man, that is just so not fair! You got Pop Tarts, her brother got Pop Tarts, she paid for Pop Tarts with her own money and didn’t get any at all! And anyway you wouldn’t have even had pop tarts if she hadn’t e-mailed you, so, like, basically those Pop Tarts should be hers!

          …Is it a bad thing that I can still put myself in the shoes of a tween fifteen years later?

          1. Not usually Anon*

            She was made whole – the Pop-Tarts were replaced by the offending party who wasn’t even her brother…but her step-dad who’d taken them to work (he didn’t know they were hers – that’s why we use post-it notes, people).

            And she had to apologize to her brother for unjust accusations and trying to get him put up for adoption.

            1. Former Teller*

              This is one of the funniest things I’ve read all day. This is why I love this blog and it’s followers.

    1. Bridgette*

      LOL Thank you for a great story. I’m glad it turned out alright. And this: her filter between having a thought and needing to email Mom immediately wasn’t working. Yes. I was a teenage girl once. I remember such life-altering devastating events as having the wrong conditioner.

    2. Chinook*

      I want to add mine. IT guy and I arranged for him to fix my computer. He sent me a meeting request, which I accepted and was then confused because it never showed up in my calendar. I went back to my outbox to see if I was imagining things and I noticed it was sent for 1AM.

      I followed up by saying that it work only if he brought the wine. He called me, confused. I pointed out the error and you could here his laughter through 2 floors. After that, he always offered me beer with every computer repair!

  4. Amouse*

    Aw, you sound like a very sweet boyfriend to be this concerned about it but I agree, it’s highly unlikely.

    The most cringeworthy (in a sweet way) thing that ever happened at my work was when our blind employee (this amazing man who is one of our IT systems analyst) accidentally sent an e-mail intended for his girlfriend to the whole company. It didn’t contain anything racy, it was just cringeworthy that it happened to him.

  5. Not Usually Anon 2*

    My best friend once texted a picture of herself in bed (it wasn’t “sexy” per se, there was no nudity, but still, bed is a bed) with her and her bf’s dog and wrote “Come snuggle, we miss you!” to a coworker with the same name as her boyfriend.

    She didn’t realize the mistake until he responded with “What’s your address? I’ll be right over.”

    Yeah. That was awkward. Luckily he was a mature guy (and, I think, a bit embarrassed himself) and they both pretended to forget it.

  6. oversharer*

    Granted, not an email story but oh so cringeworthy. I was at a small start up a few years back… it’s not unheard of to work on your own equipment (laptop), so obviously personal stuff is on there as well. We only used our own machines and 99% of my work was done really on the web, not “on” my machine, not sure if that’s clear. No MS Word or stuff like that…or saving to the actual computer, except…
    I had a Perl code execute-y question, not usually my area, and the much, older, industry icon of a gentleman assisted me. While he was driving, on my HD’s file list I noticed you could barely make out the name of a file with a big title something about a mildly sexual, very irreverent prenup. Ahem. You really had to look for it and know it was there, but I knew it was there and sufficiently mortified couldn’t get my question answered fast enough. And to this day won’t use Perl ;)

  7. businesslady*

    my two embarrassing mistaken-email-address stories:

    1) many years ago, I replied to my improv group (who I wasn’t particularly good friends with) instead of forwarding an email to my boyfriend/now-husband. fortunately the text was just “hey, oh, I forgot I had this show Saturday night, but maybe we could do XYZ before/after.” (fortunately XYZ was G-rated, & I hadn’t included any choice words about my castmates, but still.)

    2) recently I forwarded an Amazon suggestion email re: the availability of Van Halen’s For Unlawful Carnal Knowledge…to some random other person in my organization whose email address starts with the same three letters as my husband’s. the email only said “you don’t say…” but it would’ve been nice if the album hadn’t had a racy title. I sent an apology email, & the accidental recipient never responded, so we’ll assume that one was ultimately fine, too.

    …this isn’t QUITE the same as inputting the wrong address, but I also learned the hard way that if you forward an Outlook invite, the sender gets a copy of what you wrote. a coworker I didn’t particularly care for was having a BBQ, & I forwarded it to my husband with some commentary that was pretty ambiguous (THANK GOD) but not great either; something along the lines of “oh, hey, there’s this; I’m not sure you’re invited but I’ll have to go.” my coworker mentioned it, clearly choosing to interpret it as a neutral message (& saying that husband was definitely invited), & I responded in kind, pretending that I wasn’t mortified that he’d seen it. & honestly, it could’ve been SO MUCH WORSE given how much I disliked the guy.

    but let that be a lesson to anyone else who uses Outlook. (& of course, there’s also the old adage about never sending anything via work email that you wouldn’t want to go public, but my organization considers work email private, & sometimes that makes me less cautious to problematic effect.)

    1. Jamie*

      And anyone who would complain about a VH email is someone to be looked at with deep suspicion.

      If someone had done this to me they would have instantly become my new BFF. Unless my boss had tickets which were being given away – then they would be my mortal enemy.

    2. Bridgette*

      I’ve experienced the private commentary problem when emailing with coworkers/clients who then forwarded my comments to the person being commented on. Fortunately they weren’t bad, but I was mortified that something I said off-hand was then sent directly to that person. Usually it’s in the form of a context-free question from Coworker, and I don’t realize it was Client that asked them, and then Coworker forwards my comment.


      1. businesslady*

        @Jamie–haha, I was hoping you’d see this! :)

        @Bridgette–I’ve never done that (thankfully), but I’ve been on the receiving end (i.e., been copied toward the end of a long email conversation where there’s stuff in the thread that I probably wasn’t meant to see…)

        1. Anonymous*

          Once, having inherited the finalization of a troubled report that had been outsourced to us, I received an email from the client contact with a long thread including one that began with the instruction that we (the report writers) were not to see it. Either it was forwarded in error or someone was engaging in passive-aggressive troublemaking. The client’s unhappiness wasn’t new information – and the person writing the complaint had asked it not be shared – so I decided to see no evil and concentrate on doing what I could to address the concrete issues in the report. I’d either implicate an innocent though sloppy contact, which would make my work with them difficult, or I’d be gratifying a troublemaker, and we were all way too busy for drama.

          My personal moment of sexual mortification was realizing with a sinking feeling that I’d after I’d finished a late night work session that I’d left the VPN channel to work running while I . . . strayed. Nothing illegal, but not something you want showing up in your logs. I debated with myself for a moment, then sent a quick ‘oops, my mistake’ email to our IT guy, who emailed back – without comment – that it was fine.

      2. anon o*

        My manager has done this to me several times. One in particular – I had one supplier who was friends with my boss – she & I had a bad relationship but I was trying to work on it when he forwarded her an email I’d sent him complaining about some work she’d done and asking for his help since they were friends and he’d hired her for the job against my wishes. So much for trying to repair the relationship!

        He actually had the nerve a little later to complain to me that she didn’t like me! Incidentally, she & I have patched things up and we actually work together really well now.

        1. Jamie*

          Why do people DO this?? Stop forwarding things without deleting this stuff.

          So many people have slippery fingers with the forward button I make sure every email I send could be read in court without shame. Sometimes the snark builds up so much I just roll my eyes behind my monitors to get it out of my system.

          Someday someone will walk in and see me making faces at a screen and require me to undergo testing. That will be how my career ends – not with a bang but with a eyeroll and a ffs smirk.

          1. anon o*

            Well it was a good lesson – every email I send to him I think, “would I be OK with him forwarding this to anyone he knows?” I apply this policy to all emails I send to anyone. I save my snark and complaints for in person and on the phone.

            I’ve also worked for my supervisor for 10 years so our relationship is quite familiar and informal so often he’ll forward emails to people where he’s at the bottom cursing me out or saying things that don’t offend me in the slightest but make him look like a jerk. It’s a perpetual source of amusement.

          2. Ellie H.*

            There’s a lot of rancor between my office and people who used to be in my office before a restructuring and the main form this rancor takes is their forwarding any email from me that contains a basic request to their supervisor to “apprise” him of the fact that my office has made this request. I used to be (and we are still sort of pretending to be) good personal friends with all these former coworkers so my emails to them typically have a very friendly tone and I hate that they get forwarded. I HATE their supervisor and the whole thing drives me crazy.

  8. EngineerGirlUK*

    I had an issue with one of my works MFDs and after scanning my driving license accidentally sent it to some random in my company’s customer contact center rather than my own e-mail .
    Luckily the guy had deleted it and sent an e-mail saying so. Phew personal details safe once again.

    1. Elizabeth West*

      Not email, but I’m one digit different from the local Child Support Enforcement office, and until I changed my outgoing message, I used to get people calling me thinking I could help them with that. They would leave messages on the machine and I would delete them.

      One time a lady left her social security number on my machine, which is basically like handing your identity over to someone if the wrong person gets hold of it! I actually called that lady back and told her DON’T DO THAT!! What if I was a criminal type, or played the message where other people could hear it, not knowing?

      1. sophylou*

        At my old job we had onsite and remote patrons. Some older people preferred to communicate by snail mail. We had language on our website noting that patrons–meaning onsite–would have to show ID. One day I opened a letter from the UK and found that the patron had included some kind of official government ID (maybe the UK equivalent of a driver’s license?) Both my boss and I literally gasped out loud when we saw it. She got bumped to the top of the queue so that we could mail it back to her IMMEDIATELY. Really didn’t want to have that lying around anywhere.

  9. Construction HR*

    Back in the early days when we still had dial-up, we had a sales employee send a quote to the right last name / wrong first name. Both were purchasing managers and the right one’s company was a much smaller customer than the wrong one’s. Big problem was that the smaller company was getting better pricing than the big company ended up costing us millions of $$.

  10. Amouse*

    So long as we’re talking e-mail mistake stories…
    My worst gaffe with e-mails was a few months ago when my best friend e-mailed me and our two other best friends that she was pregnant. I immediately e-mailed a congratulations to her. Then in my excitement I e-mailed what I thought were my other two friends the idea of a “surprise” baby shower to one of my other friends–and the friend having the baby! This was pretty dumb of me. Either way it worked out because she thought it was thoughtful of me lol

    1. Anon*

      That’s not so bad – when I was reading your comment, I was worried you had e-mailed you friends some comment about the paternity or her failure to use birth control or something!

        1. Jamie*

          Get out of my head – I was just typing Maury Povich in a reply to Anon!

          And if your friends don’t want you to get excited and do fun things for them like throw showers then they shouldn’t do exciting things like get pregnant – she has only herself to blame.

          1. Amouse*

            haha! You were seriously thinking Maury? I almost typed Jerry Springer and then changed my mind. Maybe it was telepathy :P I know! It’s her fault really. But man I felt so dumb. The plus side is we totally changed the date of the shower from what I suggested and we totally changed it from a shower to a surprise spa day for her cause her sister’s already throwing her a shower so she’ll have no idea what’s up ahead :-)

            1. Jamie*

              Someone mentioned something about the Borg on another thread here the other day, so I asked my Trekkie husband about it and from what I could gather it’s some kind of mental collective? Different entities, one brain?

              Something like that – I kind of stopped listening because I plainly said if you can’t explain it to me in under two paragraphs I’ll just go to Wikipedia – because I didn’t want to dance all the way down the Enterprise road …but no…that was about 15 minutes of my life I won’t get back. It wasn’t so bad after I dozed off.

              Anyway, my point is I think Alison has some kind of alien code embedded in the site and we’re becoming a Borg.

              Unless I’m using the reference incorrectly, then I have no point. Seriously, my brain stopped working a while ago. Time to go home yet?

              1. Amouse*

                “We are the Borg. You will be assimilated. Resistance is futile” I love Star Trek very much and Buffy and now Big Bang Theory which I just began watching. Regardless, I think your theory is entirely plausible. It would explain a lot of things :-)

                And no it’s not time to go home but I do get a cupcake in 10 minutes!! woo!

                1. Jamie*

                  If you like Buffy please give Grimm a shot. It’s by some of the same creators and has the COTW and arc thing happening and it’s super awesome and I don’t have nearly enough people in my life to talk to about it.

                  I want a cupcake. Does yours have rainbow sprinkles?

                  I feel so guilty right now because the OP is an awesome employee who just wants to be more productive and I hit the wall over an hour ago and I can’t look at this code anymore and I’m very whiny about working tomorrow although it’s my own stupid fault for not getting more done today.

                  Seriously, I’m working on this problem that I know the answer to. I’ve run data like this before – I know this…but it’s eluding me. It’s like the answer keeps flitting away to another corner of my brain just out of reach.

                  Thing is I know that it will come to me just as I’m drifting off tonight and I’ll finish this project in a hail of victory. Why can’t I pull knowledge in my head on my time table…it’s like my brain is working at cross-purposes with the rest of me.

                2. Amouse*

                  Cool! I’ve heard about Grimm. Perhaps I shall. Do you watch Once Upon a Time? It’s got Jane Espensen who worked on Buffy as a producer.

                  I got a mini pumpkin spice pumpkin with cream cheese icing. It was small but so delicious. Ever since I learned the big ones have 600 cal I’ve been veering in the direction of the minis (about 200 cal) I know calories shouldn’t matter but I cannot just eat whatever I want without consequence so some compromises must be made.

                  You’ll figure out your work problem when you aren’t thinking about it but i know how frustrating that is in the moment. I hope the day’s almost over for you and you can go home soon :-)

                3. Diane*

                  I should be writing and rewriting something now so I don’t have to work on it this weekend, but I’m reading about hitting walls and cupcakes and realizing I really must tell you all my amazing invention:

                  Pumpkin coffee cake with nutella swirls. I know, right?

                  My version is also gluten-free. Next time, I’ll write things down and make a proper recipe.

                4. Job seeker*

                  Alison, I am impressed. About your repairing a closet door just from watching a video on how to. Is there anything you can’t do? I wish I was just half as knowledgeable as you are. I really mean this. You are someone I wish I was more like. I don’t think I could repair anything and it look right.

                5. Ask a Manager* Post author

                  Ha, there is MUCH I cannot do, believe me :)

                  YouTube is pretty amazing for figuring out how to do stuff though — from applying eyeliner to fixing closet doors!

              2. Rana*

                Short version: The Borg are a hive mind. When they meet new people, they attempt to assimilate them into the hive mind by turning them into cyborgs. Their catch phrase is “Resistance is futile.”

                You’re welcome. ;)

                1. Rana*

                  (I have a husband who is also prone to giving me mini TED talks in response to idle questions rather than the two-sentence short answers I really want. Oh, well, sometimes I learn interesting things…)

                2. Jamie*

                  Mini-TED talks! Awesome word smithing. I’ve got one coming up n about 10 minutes since I asked a question about part of the fence he’s repairing and he went to go make a pot of coffee so we can talk about it when he gets back…

                  I’ll just look at it as a learning opportunity and not just sit there silently frustrated wondering when hes going to answer my nly question which was “when are you going to Lowes.”

                3. Ask a Manager* Post author

                  “So we can talk about it when he gets back.”


                  This morning I repaired a bifold closet door (thanks to a repairman’s video on YouTube) and can totally imagine buttonholing someone over coffee and telling them all about it. I have a feeling of triumph.

  11. Lawyerlee*

    Funny thread! I can’t claim this one as having happened to me, but rather to a secretary in our law firm. We have a boss who is rude and a notorious tyrant, especially to her. She coped by occasionally sending emails to other employees detailing his latest offense. In this particular email she accidentally added him as a recipient. Her complaint regarded his habit of dictating letters into his dictaphone while on the toilet. Apparently much more than the contents of the letters were recorded. He did mention it to her but she didn’t get fired and he never did it again!

  12. Catherine*

    Ahh human error. My real name is rather common, and it serves as my personal email address, so I get random emails with some very personal details all the time. Once I was sent a car insurance quote with SS numbers, another time I was added to a football booster club mailing list, I keep getting reminders for someone else’s student loans, etc. I try to email these people and let them know their mistake but many times they don’t take my email off their list or correct it and I eventually block them (I’m looking at you, football booster club!!).

    1. businesslady*

      ugh, that sucks. I have the same thing, & my first initial/last name aren’t common at all. yet at least one person–possibly several–clearly THINKS their email address is actually one of my gmail addresses. & of course, I have no way to contact them & let them know.

      I’ve gotten all kinds of weird subscription-only emails, a confirmation for tickets to the Avengers purchased through Fandango (in another state, sadly, or I would’ve considered going…), & once, a huge PDF of legal documents related to the sale of some business thing…? in the latter case, I responded to explain that nope, wrong person, but seriously–how hard is it to know your own email address?!

      1. Jen in RO*

        That’s so weird, I thought it was only happening to me! I get the weirdest stuff in my inbox. You’d think people would realize that they’re using the wrong email address! I’ve also replied to the senders sometimes, but I haven’t heard anything back… I hope they did say something to the “real” Jen who thinks my address is hers.

    2. Elizabeth*

      I’ve been on gmail since almost the beginning (a friend works at Google and got us into the beta test before it officially went outside the company), so I have an email address that is first initial, middle initial, last name. Since the FI/MI combo is the single most common in the US for my first name, there are a LOT of women who have it, but a relatively small number with the same last name.

      So far, I’ve received an elderly woman’s Power of Attorney forms from her daughter-in-law that were being sent to a nursing home, all of the payroll information for several small business in the Los Angeles area, and the bills for a Kohl’s charge account. The last one, based on the zip code & street address listed, I was able to track down to a specific person who is a professor at a university and got her set up to get her bills.

  13. Anonymous*

    The other day I received a response to an email someone had sent to a opiates rehab center, complete with information on the cost of the treatment and what it entailed. It didn’t have any personal info on the person, but what this treatment would cost was insane! I replied back to let the writer know it it was mis-sent.

  14. Lilybell*

    Oh, I know you are mortified but absolutely nothing bad will likely happen. A woman at my office accidentally started “sexting” me from her work bberry a few months ago. She was dating another coworker and accidentally sent the messages to me. Awkward! We get along well so I wasn’t that embarrassed to let her know what happened. She took it way better than I would have. And she just married the coworker for whom the texts were meant!

  15. Melissa*

    My turn for an embarrassing story!

    Back when I participated in an online role-playing game (a MUSH) I sent details for an upcoming event to the shell account for my office so I could print it at work and make sure all the coding was correct. Or so I thought. Turns out I sent it to a national listserv for people in my profession, and didn’t realize it until I saw it on the day’s digest.

    I sent an apology to the list, and luckily several people responded that it was okay. Two even asked if they could come to the event! :) Ever since then I’ve avoided using nicknames for email accounts just to be on the safe side.

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