I have a crush on an older coworker, my wife read her boss’s diary, and more

It’s five answers to five questions. Here we go…

1. I have a crush on an older coworker, and we’re hanging out outside of work

I am a 21-year-old male who has worked for the same men’s clothing company for four years now. I have worked at a few different locations. For three years I worked with an assistant manager who was 15 years older than me. We got along so well and would have deep intellectual conversations and agree with each other most of the time. I have always secretly had a crush on her but have been afraid to tell her because I felt it could potentially damage our relationship.

She recently got promoted to be manager at a different location closer to my house. I visit her frequently and lately we have been going on late night hikes twice per week. Keep in mind I am not your typical 21-year-old. People tell me frequently that they think I am in my late twenties or early thirties because I present myself in a more formal / structured manner.

How should I approach the situation? What should I tell her? It’s been eating away at me for three years.

Is she currently in your chain of command? If so, it’s a definite no-go; if she’s in your chain of command, she can’t be involved with you in that way, even if she’s not your direct manager.

But if she’s not in your chain of command and there would be no appearance of impropriety (or actual impropriety) … well, what kind of vibe are you getting from her? Especially when you’re colleagues, whether or not to declare yourself needs to be based not on how you feel but on your sense of how she feels. Is she being flirtatious / sending interested signals / making social overtures herself? I’d normally discourage you from pursuing anything, because women need to be able to exist at work without being hit on when they’re friendly and also because of the age difference, but those late night hikes sound like you’re certainly close. Of course maybe she just likes hiking.

But 21 and 36 is a big age difference. You’re not that far removed from being a teenager, and she’s closer to middle age than adolescence. Some people have made that kind of thing work, but being in such different life stages tends to mean different interests and priorities. (Although for all I know, maybe you’re both interested in a short-term fling where the age difference won’t matter as much. Still, I can’t not flag it.)

And of course, asking someone out is always a risk. You need to be prepared for the possibility that she’ll say no, and that it could make things awkward between you. You’ve also got to be resolved that you won’t be the one making it awkward if that happens — that you’ll go on being warm to her and not be weird or resentful. In theory, if you’ve got all these bases covered, you could simply say, “I enjoy spending time with you. Could I take you to dinner this Saturday, not as coworkers?” … and then see how it goes from there. But that age difference is a big one.

2. My wife read her manager’s negative thoughts about her

My wife was dropping mail on her manager’s desk. The manager’s diary was open and my wife read what was written. It was about my wife, saying that she was lazy and pissed around. My wife knows she shouldn’t have read it but now feels depressed that her manager thinks so poorly of her. What should she do?

Was this a diary in the British sense, meaning a calendar, or in the U.S. sense of a personal journal? It doesn’t change the advice, but I’m having trouble picturing “Jane was lazy and pissed around” on a calendar … and if it’s more of a journal, it’s an odd thing to keep out at work.

In any case, your wife now has the advantage of knowing what her manager thinks of her, when previously she didn’t, and that’s useful. Does she think there’s any truth to what the manager wrote? Does she know why her manager feels that way, or does it seem completely out of left field? If she understands why her boss has that impression … well, it’s a wake-up call to change that if she’s bothered by it.

But if she can’t imagine why her manager thinks that about her, one option is for her to ask to meet with her boss to talk about how her work is going. Without saying she saw the diary, she can ask for feedback and try to open a conversation about the manager’s assessment of her work. It’s possible your wife has info that would change her boss’s impressions (for example, “I’ve been finishing X on time every week but it’s getting hung up with accounting”), or it’s possible the boss has info that would change your wife’s thinking (like she needs to loop the boss in every time accounting delays something, or she should be prioritizing Y over Z, or so forth). But even if nothing concrete comes of the discussion, remind your wife that it’s better to know where she stands with her boss than to be oblivious to it.

3. What do you say when you had a horrible Christmas break?

While my Christmas was nowhere near as bad as I’m sure lots of people’s were, I’m still wondering if you have any advice about what to say if you didn’t have a good break. I’m very lucky to be in a stable, remote job and no one I know has been unwell this year, so I know how lucky I am. Nonetheless, I haven’t seen any of my family for over a year now (since last Christmas) and here in the UK the regulations changed at the very last minute, meaning that after looking forward to seeing them for months I was left at home alone with two days notice.

Most people at my work have been ignoring covid regulations in their personal lives so far and mixing anyway, or they live close enough to see each other, so they all had great christmases. What do I say when they ask about mine and I just want to burst into tears?

As a general rule, when you don’t want to get into a topic (especially one that people are often asking about simply to be polite / because it’s a social nicety), you can usually give a very short, vague response and then immediately ask about something in their life. So in this situation: “Oh, you know, 2020 … how was yours?” Or: “Well, I’m glad 2020 is over! How was your break?” Most people won’t press for a detailed accounting of how you spent your time, but if someone does (which is rude!), it’s fine to say, “Eh, nothing much to report! So tell me about (subject change).”

4. Unemployment says they overpaid me and wants repayment — but I can’t reach them

While at my last job, I had to get surgery to save my life and, due to the pandemic, had to move it a few times. I turned in two dates for the surgery; a week later I was fired. I filed for unemployment and have gone back and forth with Unemployment in my state. When I lost my job, HR refused to tell me why. It turned out, they originally told the unemployment office it was due to misconduct and later changed it to employee performance. I received a settlement for unemployment. However, now the state says that it was an overpayment and they’ve asked me to return the payment, plus extra. I can’t get in touch with the unemployment office because my calls have been unanswered. What are my options?

I’m scared because I may have to file for bankruptcy from these medical bills, and the unemployment insurance would cover the lawyer’s fees.

Lots of people don’t know this, but your elected representatives can help with things like this. Call one of your members of Congress, your state legislators, or your governor’s office. All of those offices have constituent services staff who will help when a constituent is having trouble with a government agency. Call and briefly explain the situation and that you haven’t been able to reach anyone, and they should be able to help, even if it’s just getting the unemployment office to call you back. They are often tremendously helpful! (There may be states that are exceptions to this, but I’ve recommended it to a lot of people recently who had had trouble getting through to unemployment and they’ve all gotten help.)

Also, please consider contacting a lawyer about the firing. Firing you right after you said you needed surgery and lying about the reasons is highly sketchy and a lawyer may be able to help you get some compensation from them. Lawyers will generally have an initial conversation for free, and in many cases if they’re confident about their ability to get a settlement, they won’t charge you for their work up-front. (This doesn’t even mean you’d need to sue; lawyers can often negotiate settlements in exchange for not suing, especially when it’s clear the employer messed up.)

5. Naming a high-profile client on your resume

I previously did some consulting for a big-name client. Let’s call him Will Yates. I would like to discuss this work, and name this client specifically, on my resume and CV. My thoughts are that it would show that I am accustomed to high-level work, often under high-pressure, with high-stakes and under the public eye.

However, is it indiscreet to use the client’s name? Does it also run the risk of seeming like name dropping?

There is nothing particularly sensitive or controversial about the work I did for this client, and as it was a couple of years ago, it has since all been made public; in fact, that was the intent of the work.

Nope, this is fine to do and people do it all the time. Just check with the client first, unless your name is already publicly associated with the work. The exception would be if a confidentiality or non-disclosure agreement prohibited it, but it doesn’t sound like that’s the case.

{ 445 comments… read them below }

  1. Heeryor Lunboks*

    Echoing the advice to LW 4 – I used to work at a state agency handling constituent affairs, and when we got a contact from a legislator, it went to the top of the pile and guaranteed an immediate call or email back. It shouldn’t work that way, but it does.

    Sorry you’re going through all that. Good luck!

    1. London Student*

      In your experience (and others who know about these things) does this have any impact on raising the profile of the agencies? I’m wondering if shifting calls to legislators makes it more ‘their problem’ and helps them realise more viserally how many people are using a service/waiting on a service….which in turn can help the service advocate for themselves re: funding/staffing?

      1. Green great dragon*

        It can do, yes. Not a straightforward numbers game, but you’re telling your elected representatives what matters to you, and when those reps have to choose what they’ll focus on/what issues they’ll raise, they’ll take account of what problems they’re hearing. And ideally they’ll be pushing for more funding for the agency, rather than taking up agency staff time demanding simple answers to complex issues. Ahem.

      2. LQ*

        No, this makes it worse. Legislators just get angry at the people who actually DO the work, threaten to cut funding, but also ignore the people who don’t call them. So they are full of anecdotes and don’t care about the real problems, the people waiting patiently in line, because no one is calling them now.

        I don’t want our agency to have a high profile. Unemployment isn’t a service. It’s a program that helps people but it’s not something that needs a public campaign, that’s how you get lots of people contacting unemployment about their stimulus checks, or just because they need help. Which overwhelmed offices are not equipped to handle. Unemployment is not a universal basic income, it’s got a lot of regulations about who is and is not eligible and those laws still need to be followed if the program will remain. But that’s not what legislators want. They want this one person who called them with a sad story to get help and they don’t know that sometimes unemployment isn’t the right help. They just pawn them off because the person on the phone said unemployment.

      3. Anne Elliot*

        In my experience, it does not raise the profile of the subject agency in any positive way, it’s more like, “Here’s something bad we’ve heard about your agency” or “Why haven’t you handled this?” It can be an effective way to get some movement in situations like this — where you can’t find a live person or get a call back — but the very fact that the person has been compelled to reach out to their representative for assistance does not look good for the agency.

        1. GreenDoor*

          Anne Elliot, I must disagree somewhat. I worked for an elected official and mnay times people called us simply because they had no idea who to call, not because they were mad at a particular agency. And that’s fine! It’s one of the jobs of elected officials to connect citizens with government services. REgular Joe’s aren’t expected to know all the ins and outs of government – that’s why they elect representatives.

          And it sure does raise an agencies profile. IN my home state, the public is becoming aware of just how outdated the software and systems are in our Unemployment office. We also take note of how our state legislature hasn’t met in session in over 9 months (!) to do anything about the pandemic – including allocating more resources to clear the unemployment backlog.
          So yes, OP, do call your elected official!

    2. Marillenbaum*

      I have worked at a federal agency, and we had a requirement to respond to all Congressional inquiries within three business days. Their constituent services number (for both their Washington and district offices) is typically easy to find on their website. When I was an intern in a Congressional office, being able to transfer people to our constituent services staff who could actually help was a joy–not least because it meant I wasn’t getting sworn at for my boss’s positions, or expected to listen to long and involved conspiracy theories.

      1. Anonapots*

        Haha! I’ve placed interns in the DO of an elected official and I have heard the tales of getting to know that one person who calls daily, to the point where when they do call, it immediately gets transferred to someone higher up who can nod, agree, and then politely hang up. This particular elected official does not have voicemail set up during the day and prides himself on every call being answered by a person during business hours.

    3. Policy Wonk*

      +1 on this. However, be sure you are calling the right level of government. Your Congressional rep helps with federal issues, like passports, the IRS, social security. Unemployment is likely a state function, so contact your state representative. (I used to work in a Congressional office, and we got calls from people for all kinds of issues – state, local, and things that weren’t government at all. People got really upset when we couldn’t help them – seemed to think their Congressional reps were all-powerful!)

      1. Dawbs*

        Yeah, I usually recommend starting at the state level. They can point you up the chain if you need.

        (And they tend to like non-crazycakes problems they can solve-it means you’re that much more likely to vote for them next term!

        And trust me (as someone who helped maintain the constituent database) if they can help with it and you’re not the unhinged conspiracy spouting person wanting to get the alien spaceship wreckage off their property, they’ll want to help

        1. Dawbs*

          (But also, I’m sorry. The situation is gut wrenching from here. Its awful and unfair and I hope it is resolved well)

    4. Ripley Jones*

      LW4 – I have no advice but damn, I am so sorry. I live in a country with universal health care and I can’t even imagine what it must be like to have to declare bankruptcy over a medical issue :(

        1. Jay*

          This is true. Many hospitals and some physicians will negotiate payment plans or reduce the total amount due if you ask, but that’s a daunting thing to do and can retraumatize people who already had a serious illness. The American medical system: more money for worse care than anywhere else in the industrialized world. (I’m an MD and thus complicit in this mess)

          1. 'Tis Me*

            That bit where insurance companies get to decide who gets what treatment, rather than the doctors being able to make the best decision for the individual given their circumstances, bothers me.

            Also the bits with people charged for much-needed ambulances, discouraged from seeking much-needed medical care, being put off preventative care by costs, unable to afford essential medicines… Also that bit where apparently medical billing can be really confusing with several invoices to pay for the same treatment, with some services potentially not covered by insurance even though others are and these all relate to the same stay. And the fact that worrying about sorting it all out does not help somebody rest, relax and recover. And the bit where people may well feel to get back to work before it’s recommended…

            I was under the impression that the very rich (and those with excellent insurance policies) do get amazing, cutting edge, worldwide first class treatment though?

            1. A*

              Maybe? You have to be in the 1% for that though. I work in “the greedy professions” (ie consulting, corporate law, etc) and have bachelors and masters degrees. I have “good” insurance. And I still have to fight to get stuff like broken bones and pneumonia covered with in-network insurance approved doctor. It’s a mess, and one I’m only able to get time to sort through because I’m lucky enough to have resources. Maybe Jeff Bezos can get cutting-edge cancer care or something if he needs it, but you don’t have to be poor in America to get bad health options, although it’s much worse for people who are

            2. many bells down*

              My daughter just recently had a huge ER bill, and when I looked into it I discovered the insurance hadn’t paid anything… because the hospital billed the wrong insurance. She has Company A and they billed Company B. Even the hospitals can’t get it right sometimes!

              1. KaciHall*

                My son’s insurance denied the claim for his broken foot because they aren’t his primary insurance. I told them that they are his ONLY insurance, and they told me someone told them he had other insurance. I would really like to know who else wants to pay for my son’s health insurance which is the only reason I’m working at the terrible job I currently have…

                1. Liz*

                  When I was injured in a car accident, they kept trying to bill my auto insurance company as primary. Every time I was in, I’d switch it back to health insurance primary, auto insurance as secondary. Is it possible something like that is happening?

            3. Indy Dem*

              This is my favorite meme about Insurance Prior Authorizations…
              My Doctor: You need this medication.
              MD to Pharmacy: She needs this medication
              Pharmacy to Insurance: Her doctor says she needs this medication.
              Insurance: Does she though? Let’s ask her MD.

          2. SometimesALurker*

            While the only real remedy for this is systemic change, one stopgap is the nonprofit organization RIP Medical Debt, which buys up and forgives people’s debt. There isn’t a way to apply to be a recipient, as it’s done in bulk batches, but it’s an excellent place to rage-donate if you have a little money to spare and are feeling overwhelmed by how awful the U.S. system is.

            1. Ophelia*

              Also, if I’m thinking of the right group, because they buy it up pennies on the dollar, a donation of, say $10 might forgive more like $100 of debt, which is pretty great.

              1. SometimesALurker*

                Yup! They buy it at the rates that debt collections companies charge each other, rather than at the rate the consumer pays to pay it off.

            2. MarfisaTheLibrarian*

              I’m so glad to find out about that company! I’ve been trying to decide where to donate this year, and I like donating to places that really have a permanent outsize impact, which this really does!

            3. nonegiven*

              From Wikipedia page for RIP Medical Debt:

              >The charity states that they pay about $1 for every $100 of debt that they purchase.

    5. Jessica Fletcher*

      Agreed. I think the best option is LW’S state representative. They help with this sort of thing a lot! LW, if your paperwork offers the opportunity to appeal the decision, do that right now. Unemployment offices are notoriously hard to reach by phone. And if you have an appeal right, they’ll tell you to do that anyway.

    6. Grits McGee*

      Another benefit of going through a legislator is that they probably have a point of contact they deal with all the time, and that person can get the OP a more direct method of getting in touch. I work a federal agency and we handle this kind of thing all the time.

      I’ll also say (at least for my agency) phone communication is iffy at the best of times, and almost impossible right now with the majority of the agency away from the office. That might be why the OP is having such a hard time getting in touch with someone. That’s another reason to bring in help!

    7. Sangamo Girl*

      Alas, this is an unprecedented time and even calls from state legislators won’t help you in my state. The state is large and between the unprecedented number of people seeking unemployment and the unimaginable amount of fraudulent claims, the system is near collapse. I’ll keep you in my thoughts LW 4 and hope for the best.

    8. Drago Cucina*

      I’ve had good outcome reaching out personally and professionally to my state and federal representative’s offices. Just getting a response back in a timely manner makes all the difference. I had an issue with my state retirement insisting on a military document that didn’t exist. It didn’t matter that I sent them a VA document stating that during X years the Army didn’t issue this document. I talked to my congressman’s staff, within a week the situation was taken care of. It shouldn’t work like that, but it does.

    9. H.C.*

      Agreed as a local gov’t agency employee; as soon as we get contacted by a deputy from city council or county board of supervisor office regarding a constituent issue, it’s basically “drop everything and work on this now!”

  2. Who Plays Backgammon?*

    LW 2 – My first thought was that your wife’s boss wanted her to read her comments about you. Do you normally carry in the mail and about the same time every day, or otherwise have access to your boss’s office? If so, leaving the book out could have been major carelessness, but it looks pretty sketchy to me. Like maybe the boss wanted your wife to have this unfavorable feedback but didn’t want to speak with her about performance issues.

    1. Who Plays Backgammon?*

      Sorry, I switched up my pronouns up above, I meant to refer to the wife, not the LW.

    2. allathian*

      Sounds more than likely to be the case to me. If that’s the case, I wonder what the manager’s trying to accomplish?

    3. Uranus Wars*

      Yes, so it jumped out at me that the notebook/diary was out in the open, and well, open.

      I keep a notebook where I write down notes from my employee meetings…BUT I don’t put opinions and I certainly don’t leave it out, or out and OPEN. My goodness. I try to write it factual and unbiased “employee did this, I said they, they responded this, this was our agreed resolution”…everyone might not do that neutral, but I still am blown away by it being open. Unless OP and manager just had a meeting and the manager got called away to an emergency. But I would still think she’d close it if she wanted it to remain secret.

    4. Tupac Coachella*

      My first thought was that this could be some kind of weird test (of Wife’s discretion? nosiness? honesty? WTH would Boss hope to achieve?). It would be paranoid and unlikely to do anything but freak Wife out, but we’ve seen bosses do a lot weirder.

    5. HR Exec Popping In*

      At my organization it is very normal for people to use a journal of sorts at work and write down to do lists, notes from conversations, project details, meeting notes and yes, performance notes. I think this is a cultural norm in some companies. Leaving it open and unattended would be a no-no but I do not think the manager left it open as a test or to intentionally have the employee to read the notes. This should be treated like anytime an employee accidently sees information on their own performance assessment – like when you find an email or a copy of your review form on a printer.

    6. Seashells*

      It does seem like it was intentionally left out and open. My sister used to do this with her ex-husband when he wouldn’t talk to her about something.

    7. Massmatt*

      Interesting, I had a very different take—that the boss had an expectation that underlings wouldn’t read things on her desk while ostensibly dropping off mail, and that the wife’s behavior kind of validates the boss’s negative evaluation of her. She’s supposed to be working, not reading the boss’s diary!

      I’m very surprised Alison did not spend one word talking about this violation of privacy. Yes, it was bad judgment for the boss to leave that out, it was worse judgment for the wife to read it.

      Alison seems to think this is an advantage for the wife, knowing what the boss really thinks. Maybe employees should snoop around their bosses more, seeing if they can read their diaries and email, and hold their mail up to the light to see if they “just happen” to be able to read through the envelope?

      1. LB*

        I don’t think that is what Alison is advocating for here, I think perhaps she took it on good faith that it was an accident.

      2. I Wrote This in the Bathroom*

        If it is open and on a desk that I am dropping off the mail on, I wouldn’t be able to avoid seeing what’s in it. It’s like driving past a billboard that says BETTER CALL SAUL!!! and then being accused of snooping because you weren’t supposed to read the Saul bit. It’s, like… right there in my face.

        1. GothicBee*

          This. If the handwriting is fairly legible and it’s just sitting out on the desk, it’s not that weird that she saw what it said. I wouldn’t go out of my way to read something open on a desk, but if I saw my own name or happened to catch a line or two that seemed questionable as I was passing by, I’d definitely stop to see what it is. It’s pretty hard to avoid catching stuff like that, especially if you’re a quick reader. I don’t think it indicates that the LW’s wife is the type to snoop.

      3. Yvette*

        I am not so sure it was deliberate snooping. Have you ever noticed how your name jumps out at you? Like if you are in a room with lots of people and different conversations happening even if you are not paying attention or can’t really hear the absolute second your name is mentioned it is clear as a bell and your ears perk up? It is the same thing visually. Your eyes are just taking in the entire scene and your name will jump out at you.

        1. Artemesia*

          And people who read a lot are sort of compulsive about reading what is sitting in front of them. Combine that with the name jumping out and most such people would have read it.

          If the boss didn’t lay it as a trap then it is useful intelligence as she thinks about her future there and Alison’s advice is helpful — to seek out feedback and carefully think about her own behavior. If it was a ‘trap’ then that is even scarier in terms of future at the company.

          I would be thinking about job options elsewhere and be getting ready to seriously job search while trying to make sure the description was not accurate or the result of misunderstanding something I did or habitually do on the job.

      4. Ask a Manager* Post author

        What on earth? No, I don’t think people should intentionally snoop to get an advantage — I can’t imagine anyone who has read me regularly would think that. But when you’re upset that you learned someone’s private thoughts about you, it’s far better to see the painful thing you learned as useful, not to stew about it.

        1. Massmatt*

          Ok my characterization there was a bit over the top, that would indeed not be in keeping with your history of advice.

          But while I agree it’s hard to ignore something about you/with your name on it, I still think it bears mentioning someone shouldn’t be reading stuff on other people’s desks, let alone a boss.

          And yes the boss was careless leaving this around. I doubt it was deliberate but it’s possible.

          1. It bears mentioning*

            You really shouldn’t have to be told that, so I’m not sure “it bears mentioning” should be the hill you die on.

          2. Autistic AF*

            Failing to store personal information appropriately is a bigger deal (at least from a legal perspective) than reading something left out in the open, in a space you’re expected to enter.

    8. RagingADHD*

      Or maybe the wife’s boss assumed grown-up employees know how to mind their own business, and not read documents on other people’s desks.

    9. Joan Rivers*

      And I’M picturing that boss was taking notes from someone else giving feedback. Because jotting down a couple quick quotes from a conversation on your desktop could happen. But I find it odd to jot down one’s own thoughts that way, there.

      Is there anyone else who could have said this about you?

  3. Aggretsuko*

    #3, nobody wanted to talk about their break much today, even the ones who HAVE their families in the house. One said she didn’t feel like she was out at all, really. Others may feel the same as you do this year.

    1. Super Admin*

      Yeah, I agree. My team chatted briefly yesterday about our Christmases on a social call, but it was subdued and we didn’t linger on the topic. Much like you, OP3, I’m in the UK and after not seeing my parents for a long time I was gutted when things changed last minute and it meant not seeing them at all, so I really empathise and hope you’re OK – especially after yesterday’s lockdown announcement. Fingers crossed we’ll see a downshift in restrictions in Feb/March and you can have a postponed Christmas.

      1. RebelwithMouseyHair*

        Yeah my son only made it home for NY, it was our first Christmas without him in 28 years. Had he told us he’d be going to his GF’s parents for Christmas, we’d have been prepared for that, nothing more normal when you’re in a long-term relationship. But the last-minute travel ban was really hard on everyone.
        I don’t have any colleagues but I wouldn’t have had any problem saying that it was rough. I won’t be crying on my clients’ shoulders, I just lie to them.

      2. OP3*

        Thanks Super Admin – I’ve been in tier 3 or 4 for almost the entirety of last year so a lockdown doesn’t make much difference to me! I think sometimes I forget that other people out there are trying to follow the rules as so many here aren’t. I had my first day back yesterday though and it seems you’re right, even people who had a great Christmas are being sensitive about it. :)

        1. Keymaster of Gozer*

          Tier 4 here, and the very few people who’ve asked how xmas/new year was for me got a standard “hope 2021 is better” response. I don’t want to talk about 2020 again if I can help it, I’ve suffered enough.

          (Will admit to looking forward to vaccines though if the person asking is friends with me, because that generally ends the conversation on a hope note)

          1. EvilQueenRegina*

            I’m in the local authority that went down to tier 1 right before the announcement of cancelling Christmas, then 2 on Boxing Day, 3 at New Year and now lockdown so have been through them all in the space of 2 and a half weeks. I pretty much answer that way and I definitely admit to looking forward to vaccines.

            1. Keymaster of Gozer*

              One of my favourite xmas gifts was dad asking me to explain the technology behind the various vaccines to the family. My former virologist self was v v happy :)

      3. So over it in Chicago*

        A lot of my coworkers traveled with impunity over the holidays and have great stories to tell this week. It makes me feel both resentful that they made those choices while I remained buckled down at home with my family as we’ve been much of the year; and frankly also jealous. Who wouldn’t want to go to some gorgeous beach to blow off steam after the year we all just had. Makes for internally irritating conversations but the advise here is on point – people just ask what you did to be polite; if you quickly respond “oh you know we kept it low key” or something like that they’ll quickly move on. If you’re like me then it’s really just your own feelings that you have to manage.

        1. Anon in the South*

          Same situation here. I followed the “celebrate with people that live in your house” for Thanksgiving, Christmas and NY’s. I see the pictures that others share on FB and Instagram, no masks, no social distancing, celebrating with grandmother’s BFF cousin’s daughter. I’m not jealous, I’m angry that people seem to not care. We have a C-level who says in our weekly meeting “You don’t want to be the reason the company has to shut down” and I just want to scream “It’s not me! I am doing what I’m suppose to! You should talk to the ones who aren’t”. I haven’t seen my mother who was diagnosed with dementia since January 2020. Her doctors said she has to have 24/7 care and we had to move her so that could happen.

          It’s so frustrating. I’m afraid we are headed for lockdown and those that were lucky to be able to reopen might not be so this time.

          1. pancakes*

            Why not unfollow these people? Continuing to silently follow them sends a pretty powerful message that their behavior is less harmful and more widely accepted than it in fact is. People who behave in an antisocial and/or destructive way in a deadly pandemic shouldn’t feel entitled to retain the respect of every acquaintance they have.

            1. Generic Name*

              I agree. Since 2016 really I’ve unfollowed anyone who regularly makes me feel annoyed or angry on social media. Sure, maybe my Facebook feed is now an echo chamber, but I’m really only on there to see pics of friends and family’s kids and pets etc. I don’t care to see folks’ hot takes on politics, regardless of which side they are on.

              1. pancakes*

                I don’t think it’s accurate to describe that as an echo chamber unless it’s your sole source of news or information about the world, which doesn’t seem to be the case at all.

            2. Anon in the South*

              I did. They asked why I wasn’t commenting or liking anything and I was honest with them. They said I shouldn’t “dictate” their life or tell them how to behave and I said I wasn’t, I just didn’t want to see pictures of them doing high-risk activities and was not going to like something I felt was an unnecessary risk. I was called a “Karen” and other things.

              1. tangerineRose*

                Do they have no other friends, or do they keep some kind of list to make sure that all of their friends like each of their posts? They seem oddly intense about this.

                Also, what’s up with calling you a Karen for not liking their posts? Do they even know what the term is supposed to mean? (Also I hate that a regular name is being used this way.)

                1. Seashells*

                  Unfortunately, I seem to work with some people who keep a list. I tried to not friend/follow coworkers because of drama like this, but almost everyone here does so I was trying to fit in.

                  Karen means someone who acts entitled and demanding, right? Like someone who gets mad about seemingly innocuous stuff and screams for a manager?

                  Overall, I like my job and most of my coworkers are pretty good. There is a small group of people who seem to love drama and they are the ones doing the things I think are high risk.

                2. Anon in the South*

                  Unfortunately, I think some of them keep a list. I tried not to friend/follow coworkers to avoid drama like this. Most of the people are do friend/follow each other, so I ended doing so to better fit in with the culture. It had been mostly fine until now.

                  Karen is used to describe overly demanding and entitled women, right? Like the type of person who would scream for a manager if the grocery store clerk told them their coupon had expired or you disagree with their political views and they go on a rant about why you are wrong.

                  I like my job and most of my coworkers are ok. There seems to be a few like the ones described above that keep tabs on things and report their life on FB/Instagram. It used be kind of amusing to see the posts of the person who posted about the food they cooked and their nails and hair, but I dared to say what I thought them taking risks in our current time and I’m “dictating their life” and being a “Karen”.

          2. Artemesia*

            They are not transporting people who appear unlikely to survive to the hospitals in California — really bad time to have a heart attack there. They are rationing oxygen and so people who would routinely have gotten it for COVID or other problems are not now even with relatively low blood O2.

            I am not jealous of people who travel and besport themselves; right now they are putting themselves and their families at huge risk. I hate being locked down but am lucky to be able to be so and hope the few necessary forays out to get supplies don’t kill me before I can get the vaccine.

            There are some dark days yet ahead (although meanwhile apparently rich country club members in Florida were able to waltz to the head of the line for vaccine (even flying from NYC to do so) when local 1%er David Mack who controls some nursing homes used the cover of nursing home priority to get rich country club members inoculated first.

        2. lemon*

          I’m with you on this. All of my coworkers have been travelling throughout the pandemic, so the holidays were no exception. I find myself quietly seething when they’re talking about their lake houses or how the kids got to see grandma and grandpa, and I haven’t had any non-digital human interaction for almost a year because I live alone. I just give a slightly pass-ag “Oh, my break was pretty quiet because I’m being pretty serious about social distancing,” and move on. It’s hard, but I’m also not trying to start any arguments.

          1. Mr. Shark*

            lemon, I just want to say I know how you feel. I live alone as well, and this has been extremely difficult. I also am away from my “home” city so I don’t have any friends in city even if I wanted to get together while socially distancing.
            I can only say hang in there, and hopefully this will get better for everyone, and we will be able to see loved ones soon!

      4. Ace in the Hole*

        I’m in the US, but one of the regions that (fortunately!) has much stricter safety precautions than much of the country. No one here is asking much about holiday plans, because the answers tend to range from forced-cheer “Oh, nothing much just a lovely quiet day at home” at best to “Terrible, someone close to me died/is in the hospital.”

        We all know what each other did for the holidays without even asking: everyone stayed home, maybe had a zoom call with family. What else is there to report?

    2. londonedit*

      Absolutely – I’m also in the UK and all the email/video conversations I had yesterday were along the lines of ‘Well, it is what it is, hope you were able to enjoy your time off even with everything going on’. No one was expecting anyone to have had a wonderful festive time. Personally I was fortunate to have been able to decamp to my parents’ house before Lockdown 2.0 in November, so I was able to spend Christmas with my family, but the flip side of that is that I haven’t been home for 9 weeks, am now looking at a further 6 weeks minimum away from my flat, and the admin side of that is starting to be a headache. Let alone the fact that I can’t see my partner or my friends back in London.

      1. UKDancer*

        Ditto. People in my company aren’t very talkative about Christmas and the general tenor of the conversation was “ok under the circumstances, let’s hope for better things in 2021.”

        1. Keymaster of Gozer*

          One of my friends described it as the most British response to a disappointing year ever. We shrug off the question, go ‘let’s hope for better’ and put the kettle on.

          ‘Least the tea didn’t run out’ was another I heard.

          1. 'Tis Me*

            I think ‘Least the tea didn’t run out’ is definitely the most British response!! :-D

            I’m glad I didn’t change my standard tea order in anticipation of a Christmas gift of teas (my husband’s family do an open Secret Santa where you give a wishlist to somebody) as my BIL missed the bit about “redbush/honeybush possibly white tea, but can’t tolerate caffeine” (but it’s nearly his fiancée’s mum’s birthday so they’ll pass it on to her and when things are better and we can do a proper “everybody get together” meet-up I will get a replacement)…

          2. UKDancer*

            I couldn’t see one of my cousins at Christmas but I had at least sent her a tea advent calendar with a different one every day, so I could be sure her tea wouldn’t run out.

    3. Cat Tree*

      I feel like this is the ideal situation for a polite white lie. I did very little over my break. I live alone. I’m in multiple high risk groups so I didn’t visit family. For a variety of reasons, I didn’t even Zoom with any of them. I’m dealing with so much drama with my elderly mother. I’m pregnant and my appetite is super weird, so I didn’t even cook myself a nice Christmas meal (protein shakes and easy mac are about all I can handle right now). I had intentions of doing something productive around my house during my two weeks off, but I ended up just catching up on sleep and tv shows.

      But when my well-intentioned coworkers ask me how my break was, I just lie and say it was nice, and ask them about theirs. It’s just a polite exchange and I don’t really need to get into all the details.

      1. Boop*

        @Cat Tree – I’m sorry you’re having a hard time. Sending internet hugs (the safest kind)!

        The current remote situation means that our office meetings often require that everyone give an individual response to these types of questions, instead of fading into the background. To keep the impression that I am participating and don’t want to hurl the computer out the window, I usually respond with an upbeat statement or funny incident: I started/worked on/finished a project/quilt/puzzle/book; the cat woke me up at 3:00 every morning to serenade the stars; all my plants bloomed at the same time; finally watched that show/movie I had been meaning to, etc. It allows others to share their own stories or discuss their love of terrible teen melodramas/pets/hobbies and keeps the energy of the conversation going. Even if the rest of the break sucked, you can usually find one little thing to mention.

        1. Seeking Second Childhood*

          An opposite answer can be used to the same effect: We had some teenager drama about not wanting to do homework and chores, but it all worked out. How about you?

        2. Cat Tree*

          It honestly wasn’t that terrible, at least no more than the rest of the pandemic. Since I didn’t travel, I didn’t have to plan things out and pack a suitcase, or arrange a pet sitter to feed my cat, or clean my house because the pet sitter would see it, or worry about my bored and lonely cat the whole time. I didn’t have to take a long drive, potentially in bad weather, and I didn’t have to stop at a rest stop to use the bathroom and pump gas in the cold. I didn’t have to sleep on my mom’s uncomfortable guest room bed, or have the same conversation 10 times because there’s only so much to talk about. I missed seeing my family, but I realized just how much I hate traveling and it was nice to have a break from it.

    4. Birdie*

      Yeah, my office has mostly been keeping things generic. Questions like, “Did you get some rest in over the break/Watch any good tv/Cook anything interesting?” The assumption seems to generally be that no one had the Christmas and/or New Year they ideally would’ve wanted.

    5. Toothless*

      I felt like this, too – my main line has been “Not the best Christmas ever, but [insert small positive thing]!” with things like getting a home improvement project done, making a really good food item, etc.

  4. Martha*

    I am staff to a state rep and have been responding to inquiries like LW4’s all year. People often assume that electeds have dozens of staffers and respond to everything by auto-reply, but there’s a good chance yours doesn’t. I’ve been able to give folks individualized attention from a human being at the very least and actually solved some problems at best. And I have become very knowledgeable about the UI system, which I was not anticipating at the start of 2020.

    1. MtnLaurel*

      From the constituent end, my Senator’s staff has been very helpful when I needed to cut through red tape quickly to get a passport renewed. That’s literally what they get paid for, and I still keep the staffer’s card in my wallet.

    2. Boopnash*

      From another state rep staffer, I hope you’re doing ok and hanging in there! It’s been a tough year to do constituent services and we don’t often get much credit!

  5. Seven hobbits are highly effective, people*

    #3: I picked one specific, bland-but-positive thing as my “go to” thing to share about my break (what I got my dog for a Christmas present and how much fun he had with it) so I could close the social circuit without getting into how miserable this holiday season has been for me. Seems to be working well – the dog people sometimes want dog details (which is fine in my case), and no one else asks for additional info. If you can similarly find a specific bland one-sentence thing to share that might be a good tactic.

    1. allathian*

      I agree, great tactic.
      I’ve been back at work (WFH) for a week, and so far I haven’t talked much about my break. It’s been mostly stuff like “how was your break?” followed by “OK, how was yours” and “so was mine”. Everybody knows that most people didn’t celebrate the holidays in the same way that they usually do.

      1. Uranus Wars*

        And I think some peoples “how was the holiday?” is really similar to “how’s the weather where you are?”…kinda feels like an opener but detail isn’t really warranted or wanted. A simple “nothing exciting to report” works even in the best years.

      2. Quill*

        My first conversation about it was “got snowed in, won online scrabble” and that was really it.

    2. Elenna*

      LW 3: Sorry your holidays sucked!
      I was coming down here to say basically this. Find one thing you did that sounds like it could have been fun, even if it wasn’t actually fun because you were missing your fsmily. Doesn’t even have to be truthful, necessarily, but it’s probably simpler if it is. Then say something like “Oh, I did some baking/caught up on TV/slept in a lot/whatever, how was yours?” Ideally you say this in a brisk, hopefully at least somewhat cheerful sounding way, so it kinda makes it sound like you enjoyed whatever it was, but doesn’t really leave room for questions.
      A lot of the time people just want a quick two-sentence conversation to acknowledge “you are a fellow human being and I care about your happiness” in which case you can probably pivot back to work after that fairly quickly. If they’re looking for an actual conversation, try to talk about how their Christmas was, most people like talking about themselves more anyways, especially if the had a good time.

    3. Lucy Day*

      And if you truly can’t think of a positive anecdote, “it was very relaxing!” in a cheerful tone works well! The majority of people will take that as closing the loop and move on.

    4. OP3*

      This is perfect, thank you and everyone else who has commented! I read a lot of books and my cat got a new laser toy so I can use those. I don’t know why I didn’t think of that.

      1. MK*

        I doubt a lot of people had a great holiday OP! I understand that if you didn’t get to see your family, it must seem that way for others who were able to, but it’s more a case of “not as bad as it could have been, others had it worse, let’s not complain” than “the most fun we had in years”.

        1. UKDancer*

          Definitely. I’d view anyone going on about having an amazingly fun Christmas as being decidedly tone deaf under the circumstances.

          Something muted along the lines of “ok” or “very quiet under the circumstances” or “could have been worse” is far more common judging from my post Christmas chats with colleagues. Sometimes people have expanded with things like “I finally watched Game of Thrones from start to finish” or “I spent the time toilet training the new puppy” but nobody has been full of a list of exciting activities. The lady with the new puppy had the most exciting news and we got to see the puppy in question who was v cute.

          1. Anne of Green Gables*

            I’ve also used “I didn’t think about work at all the whole time” which is true, and I use to illustrate the mental break.

          2. Rusty Shackelford*

            “I slept late almost every day. It was glorious.” I mean, the bar is set pretty low this year.

            1. 'Tis Me*

              Have small children. Hate mornings. Jealous.

              I mean in fairness they largely let me stay in bed til 9:30, 10 over the holiday – but this means that now the eldest is back at school as a keyworker’s child, mornings are painful! (They were painful before the holiday too… None of us are morning people!)

    5. Green Tea for Me*

      I’ve been doing something similar. When people ask how my holiday was o laugh and say ‘oh, the cat got more Christmas presents than anyone else. As always.’ And then move the conversation along.

      Sometimes it turns to talking about pets, sometimes the conversation goes somewhere else. But I’ve shared enough to not make it awkward.

  6. Beth*

    LW1: I would honestly advise you to continue enjoying your crush quietly and not try and manifest it into reality. I don’t see anything here that screams to me that she’s into you. It sounds to me like you’re solidly friends, but I’m not seeing you say that you mutually flirt, that you have emotionally intimate conversations, that you compliment each other frequently, or that there are any other clear signs that your feelings are returned. I suspect (both from your thorough description of your relationship and from my own experience with long-term crushes) that if those things were happening, you’d have noticed and mentioned them.

    That’s not to say that she definitely isn’t into you, of course. Lack of evidence isn’t the same as a solid “no,” and under normal circumstances, I’d say go ahead and ask; sometimes we need a solid answer to move on. But given the age gap, I don’t think your odds are good. Plus, this isn’t just anyone–it’s your superior at work! Even if she’s not in your direct chain of command anymore, you’d be taking a risk by asking her out. If you want to keep her as a mentor, or use her as a reference in the future, or possibly work under her again in the future, you don’t want the awkwardness of seriously misread signals between you.

    1. Bazza635*

      This! Particularly the last sentence, there are probably more benefits to your job and career, than to be putting the hard word on her! You may lose all this and friendship for a women who is nearly twice your age. Its great you have a friend at work that you also see out of work, don’t make it weird.

    2. Batgirl*

      I think the bar has to be really high for workplace romances. Like, I wouldn’t give into a crush unless I felt this person was the one, so much so that just the chance to be with them is more important than staying at this particular job. Since she’s at a different location that mitigates things a bit and I wouldn’t say never do it but I’d move very slowly and as you say, consider if there’s any real intimacy between us.

    3. Cat Tree*

      Even if she was interested I would advise against pursuing it. The age gap isn’t ideal, but is less concerning than being coworkers.

      I get where LW is coming from. It’s weird to transition from school where you are most likely to find someone to date, to working full time where dating usually isn’t a great idea. It’s also super common to have a crush on someone older for a variety of reasons. And at 21, it’s hard to let go of any potential relationship. But LW will meet plenty of other dating options and has plenty of time to keep looking for someone else. Also, LW and the coworker probably won’t work at this place forever. If they find themselves friends when they no longer work together, it might be ok to pursue something then, but I still might not advise it.

      In my mid 20s, I had a mutual flirtation with a (same age) coworker. When I left that job, I considered asking him out but I’m glad I didn’t. I eventually went back to that company and we’re coworkers again. Part of growing up is understanding that there can be a mutual interest but it’s still not always a good idea to pursue it. There are a million other options out there that won’t make your life so complicated. It’s also possible to stay friends even when there is a mutual attraction by just not acting on it.

    4. LTL*

      I’ve got to say that I’m not a big fan of Alison’s answer for this particular question.

      The age gap is definitely a big thing that’s important to flag. OP, pretty much everyone who gets into a relationship with someone significantly older thinks that they’re “different” than other people their age. They rarely are. In fact, people who flag that they’re mentally older or more mature tend to be the very opposite. Which isn’t to say that the age gap is a dealbreaker, but please be mindful.

      But I take issue with needing clear signs from someone to ask them out. It’s pretty much the opposite of most relationship advice. You don’t know how someone feels until you ask. Some people give signs and hints, and some people don’t (because well, the other person isn’t giving signs, right?). This kind of thing is very much a “use your words” scenario.

      I also take issue with this: “You’ve also got to be resolved that you won’t be the one making it awkward if that happens — that you’ll go on being warm to her and not be weird or resentful.”

      Of course the LW needs to continue to respect her, take no for an answer, and be kind. But if he wants to take a step back from their relationship post-rejection (e.g. no more nightly hikes, or seeing her outside of work), that’s a pretty natural response.

      In hindsight, I might be misreading what “be warm” means here. If it means to continue to be warm when you see her, I agree. But if it means that LW needs to continue having the same warm relationship with her outside of work, I don’t think that’s reasonable. Friendships are a choice, not an obligation.

      LW, the main thing here is that you have to weigh the chance of getting a yes against the risk of causing collateral damage at work.

      1. LOL*

        I think it’s more his age than the actual gap. The human brain doesn’t really stop developing until age 25, and I changed A LOT between 26 and 31. It’s definitely something to consider.

        1. Butterfly Counter*

          Yes to this and the one above. At 21, you may feel more mature and you may be truly an “old soul,” but being more formal than your peers isn’t actual maturity. At 21, I too was mature, smart, respectful and often felt I could relate to older people more than my peers. In my forties now, I realize how naive I was at 21, even more so than my peers. It’s just one of those things you can’t see until you’ve been through it.

          And the age gap is a bit of a hurdle for you, but it will be HUGE for her. Though things are changing, it’s still less socially acceptable for women to date a lot younger, especially someone younger than their mid twenties. Heck, I was thirty and made a wince face emoji at a friend whose 30-year-old ex husband was dating someone who was 20. Your friend opens herself up to a LOT of judgment if she decided to date you, which, even if she was attracted to you, might be enough to deter her from accepting. Not saying any of this judgment is correct, but it’s going to happen within her own peer group.

          Personally, I’d side with those saying to just let this be an innocent crush/friendship unless she gives you clear indications that she wants to date you.

          1. MCMonkeybean*

            I really agree. If he’s been feeling this way for 3 years then I’m sure the feelings are genuine but the truth is that to any outside observer a 36-year-old dating a 21-year-old at work doesn’t look great. I was just rereading the letter yesterday with the woman in her 40s flirting with the 18-year-old. The age gap here is less and he is a little bit older… but this is not that wildly far removed from that situation.

            If I were in her shoes, even if I returned his feelings, that would probably keep me from wanting to pursue anything. Chances are not small that a relationship between them could harm her professional reputation. So if he really feels like he can’t keep silent any longer and he has to ask her out, he needs to keep all of that in mind and be completely prepared to accept “no” gracefully if that’s how she responds. And if he can make it clear up front that he will respect whatever her answer is that is even better.

          2. voluptuousfire*

            Ehh…I get where you’re coming from but it may not be that huge for her. Speaking from personal experience, I’ve been in his coworker’s shoes. I briefly dated a young man of 22 when I was 34 (not a coworker) and it was a great thing. He was 22 but was very much like this OP–carried himself more maturely, looked older, had an “old soul, etc.” If anything, I looked younger than he did at the time.

            I knew he was younger and it was definitely a bit odd, but overall we really clicked as people and that’s just too rare to pass up. I’m really glad I dated him the brief time that I did because he turned out to become a really stellar man.

          3. Kuddel Daddeldu*

            A (literally) couple of good friends of mine have a significant age gap (9 years). They met when he was in his lower twenties and have been together for 25 years by now.
            So yes, it can work!
            But they have both somewhat unconventional shared interests. Having built a company from scratch to being the national market leader and later selling it to a well-known internet major (i.e. becoming independently wealthy in his thirties combined with a very frugal lifestyle) may also have contributed to the success.
            Did he feel more mature than his peers when they met? Not at all, although he was already in his second career by then.

      2. Mel_05*

        Yeah, I think continuing to be warm just means, “You can’t be cold towards this person at work, just because they didn’t want a relationship”

        But also, I think the reason she’s giving this advice, that might not be typical relationship advice, is because this is a work relationship first and if things don’t pan out they will still have that work relationship.

        Also. It’s a massive age gap. I am the age of the woman the OP has a crush on and I was turning down 21 year olds 10 years ago, because I felt the age difference between someone who was just out of college and someone who’d been out in the world for 5 years was too great.

        Now, if I had a friendship with someone that age, I would see them almost as a child. They’re younger than my youngest sibling, they’re the same age as the last class of junior highers I mentored in my 20s.

        It’s not impossible. People have relationships with a gap that big. It’s just so unlikely that I’d advise someone to exercise more caution that usual.

        1. Ask a Manager* Post author

          Yes, exactly. In a work context, you can’t be chilly to someone who rejects you. And in a work context, you do need to see cues someone is interested before you ask them out because you can’t treat work as a dating pool; you really can only make that overture when you see signs it would be welcomed.

      3. Not A Girl Boss*

        Eh, this generalization always drives me crazy. I started college at 16 and made great friends with other 18-year-old freshmen. I started dating my now-husband at 19 and he was 6 years older than me. To be perfectly honest, he was probably a little immature for his age when we met. We have been blissfully married for 9 years. There really are people who are old for their age out there, and it often comes with the very bad feeling of being trapped in the wrong body and not quite fitting in with anyone. And it sucks to hear about how you aren’t ‘really’ that mature because, while that is true, you also aren’t as immature as your age either.

        That said, there’s so much more to making a relationship work than maturity level, mutual connection, and good conversation. One problem that my husband and I faced early on was that he had already experiencing life stages I was just entering, and he wanted to offer sage advice and save me from myself but…. some things you just need to learn for yourself. It was frustrating for him to watch me learn the hard way, and frustrating for me to never get to be the subject matter expert of my own life. But with practice and communication, we worked out a good balance and the older I got the more we felt like true partners/equals.
        Timeline for kids is also a big one, and particularly huge with the specific 21M-36F age gap being discussed here.
        I would love to opine about how all that matters is love, but its just not true. Wanting your life to look the same is much more important. I have seen a few friends’ great loves fall apart because, while their really *liked* each other, they were both miserable in their day-to-day life. In one case that was a disagreement about country vs city lifestyle, in another it was about one partner wanting to be a 9-5 type worker with time together in the evenings and the other wanting to be on C-suite track, and the last one was the classic one wants kids and the other does not. If you don’t fundamentally agree on what life looks like, compromise just means you’ll like each other but not your life.

      4. Observer*

        In social situations, sure, if you are not sure just ask. But this is not a general social situation. It’s a work place situation with some built in complications. Given that reality, checking for some real signals is a good idea.

      5. EnfysNest*

        Oh, I very much disagree with the part about stepping back if she’s not interested in dating. If I thought I had a great hiking friend who I thought was just a friend and then they asked me out and then they stopped hiking with me because I wasn’t interested in dating them… I’d be really upset.

        If the LW’s only reason for hiking with this person was because of the crush and not because of a genuine friendship, then that would absolutely not be okay. If the supervisor isn’t interested in dating and then LW cut off their friendship and stopped hiking with her because of it, it would (to me, at least) feel very much like she was being punished for saying no and like the LW hadn’t ever been a genuine friend to begin with.

        LW, if you genuinely enjoy hiking with her as a friend and would be perfectly fine hearing that she wasn’t interested in being more than friends and could continue on their friendship completely unchanged if you’re told no, then sure, you could probably go ahead and gently broach the subject. Do not “declare your love” or make a grand speech about how you’ve always thought about her romantically while she thought you were just friends – just simply offer once the way Alison suggested and if she says no, then you get to continue to have a great friendship like you already have. If you are truly friends and if you care about her as a human being at all, there is no reason your friendship shouldn’t be able to remain the same if you’re told no.

        For anyone, if discovering that your friend is disinterested in dating you (for absolutely any reason) would mean that the status quo of your relationship would change for you, then in my opinion, you would need to examine if your friendship now was even genuine or if you were just using it as a way to try to get a romantic relationship from them. No more than if you asked a friend if they were interested in becoming business partners with you or to go on America’s Got Talent with you as duet singers or anything like that and then they weren’t interested – you wouldn’t (hopefully) stop being friends with someone because they weren’t interested in starting an entirely different kind of relationship with you, and dating should be treated the same way.

        “Friend” is not a lower level stepping stone to get to “girlfriend” or “boyfriend”. And “dating” isn’t a *promotion* from being “friends” – it’s a different category altogether.

    5. Generic Name*

      Agreed. The “conventional wisdom” for determining if an age gap in dating is “ok” is you halve the older person’s age and add 7. Doing the math (please correct me if I’m wrong) yields 25. I personally find this equation dubious at best, and seems to be used to justify middle aged men dating very young women, but even by this most generous guideline, I’d say the age gap is simply too big. In fact, your coworker may feel so comfortable around you due to this large age gap because she assumes there’s no way there could be anything romantic between you and is able to freely enjoy a purely platonic relationship.

      1. Beth*

        Yes, definitely! I’m 30 (so, several years younger than this woman, if I’m doing math correctly) and would absolutely not consider dating a 21 year old, no matter how mature they might be for their age. I interact with people around that age regularly (I’m a grad student, and TAing is part of my program), and while there are plenty of 18-22 year olds I can have good intellectual conversations with and many who are very mature and handling very adult things, that’s not the same thing as being compatible for dating. There’s a huge gap in life experience between the early 20s and even the mid-to-late 20s, much less the 30s.

        I try to stay warm and mentor-y with former students who want that kind of connection, but if one asked me out, I’d very quickly transition to a strictly professional attitude. This is probably partly because of the teacher/student power dynamics, but I suspect a supervisor in a non-academic work environment might react similarly.

        1. Julia*

          Yeah, I’m in my early 30s and have friends who are a decade younger, but I’m not sure I’d date any of them. They’re all lovely and smart and mature (more mature than I was at that age!), and maybe I’m the one making weird assumptions about life stages, but I’d just feel a little strange about it.

    6. MsClaw*

      Indeed. I try not to be overly grinchy about age gaps, but this woman is literally old enough to be his mother (a young mother, but still). I think it’s much more likely that she sees herself as a mentor who has taken him under her wing and they have a nice little friendship and she’s there to help him than that she is looking to date him. If he makes his feelings known, she’s unlikely to be pleased about it. I’m a bit older than his supervisor here, and if one of my 15-year-junior employees indicated an interest in me, I’d likely be some mix of mildly flattered, amused, and baffled — but mostly creeped out. There’s likely no way to not make this weird. If you can’t be her friend, then stop hanging out and find other ways to meet people and make new friends.

      1. UKDancer*

        Ditto. I am 40 and I view my 24 year old member of staff as a protege, someone I’m mentoring to achieve his potential and a nice lad. If he were ever to express interest in me I’d be very worried because that’s not how I think of him. I mean that just would be weird and offputting because he’s so young and would jeopardise the working relationship.

        There’s no evidence she’s actually interested in the OP beyond conversation and walking.

      2. armchairexpert*

        Especially since they first met and became friendly when she was 33 and he was 18. That’s a huge, HUGE difference, and it may well have cemented how she thinks of him now.

        1. MsClaw*

          Ooof. Yeah, I missed that part. I would certainly *hope* she wouldn’t consider a romantic relationship in that case.

          I would also caution the OP who says ‘People tell me frequently that they think I am in my late twenties or early thirties’ to consider how many 21yo those people actually know? One thing I’ve seen over the years is that many people are very very bad at estimating people’s ages. So take that whole ‘you seem older’ thing with a huge grain of salt. It most likely means ‘you seem older or more mature than my vague notion of what a 21yo is like’ rather than them actually comparing you with a real group of 21yos and determining that you must be 32 due to the contrast.

    7. ES*

      An important note here is that he’s says he’s being feeling this way for three years. He was a teenager when they met and she was in her thirties, I think that really changes the dynamic.

      1. MsSolo*

        The age gap and the power dynamic and the fact op things he’s old for his years all scream ‘vulnerable’ to me – I would love to think she’s just mentoring him, but there’s also a possibility she’s grooming him. She should be maintaining professional boundaries, and night hikes with colleague who almost certainly isn’t hiding his crush as well as he hopes doesn’t feel like a strong boundary to me.

  7. BakerBaker*

    With regards to LW#2, excuse my ignorance, but can someone explain what “pissed around” means in this context? It isn’t making sense to me in American or British vernacular.

    1. Cheerfully Polite Grey Rock*

      In my experience it’s roughly equivalent to “messed around”, or generally wasted time. As in, “she was supposed to have the reports done by 10am but she spent so much time pissing around that I didn’t get them until 2pm!”

      1. BakerBaker*

        Ah, I was reading it as an adjective and not as a verb with the way the sentence was written (I couldn’t understand how one could BE “pissed around”!). Thanks!

    2. WS*

      It may be Australian – you can say “pissed around”, “farted around” or “pissfarted around”! All of them mean that the person wasted time and did nothing useful.

      1. English, not American*

        My English brain wants to replace all the “arounds” with “abouts”, but the rest is the same.

    3. TiersandTiers*

      Yep, agree with all the other comments here, and to add some more British phrases, you’d also talk about ‘dicking about’, ‘faffing around’, ‘faffing about’.

      I’d also slightly disagree with Alison’s description of a diary English. It can mean a calendar, but it also refers to the notepad where you write down personal private thoughts about the world and his wife. I’d call that my diary, don’t feel we (Brits) use the word ‘journal’ as much. I don’t see why a boss would have something that personal out, or any comments about staff – pretty unprofessional!

      1. londonedit*

        I agree. I’d use ‘diary’ to mean a book with days of the week where I’d write in my appointments, birthdays etc, but I’d also use ‘diary’ to mean ‘personal and private journal’. As in, ‘OMG my sister read my diary, I can’t believe it’, as well as ‘Let me put that in the diary for next Tuesday’.

          1. Insert Clever Name Here*

            Most US folks know “diary” as “some type of calendar” because of reading British literature and watching Acorn. But TIL it can be both something you leave out and open on your desk (some type of calendar) and something you hide in your sock drawer. Maybe we’ve all bought the stereotype that Brits have nothing personal and private to say ;)

            1. Another British poster*

              What is “Acorn”?

              Personally I’d call a private journal “a diary” and an appointment book “a calendar” though I wouldn’t blink at people calling both of them diaries.

              1. Mynona*

                Acorn is a streaming service for British television shows for Americans, cf Britbox. What confused me is why anyone would keep a diary of deepest thoughts at work. Normally that’s a personal activity. Anyway, it seems like a bad idea to keep a work diary where you complain about coworkers and then leave it open on your desk?

              2. Rebecca Stewart*

                There’s a difference between a diary and a journal and a calendar.

                If I keep a journal, I might write that I received a Christmas card from Estranged Relative, along with mentioning that it was 25 and lightly snowing that day, and that I had a doctor’s appointment to see about that lump on my wrist.

                But I talk about all the feelings that came up about seeing their handwriting, and my worry that the lump on my wrist is Something Serious in my diary.

                I put “See Dr. Smith re wrist 12:30 pm 123 Main Street” on the calendar.

                But that’s me.

        1. Ask a Manager* Post author

          ” I’d use ‘diary’ to mean a book with days of the week where I’d write in my appointments, birthdays etc, but I’d also use ‘diary’ to mean ‘personal and private journal’. ”

          Right — in the U.S., “book with days of the week where I’d write in my appointments, birthdays etc” = calendar.

      2. UK reader*

        I agree, I don’t recognise Alison’s ‘British’ description at all and checked the comments just to see if anyone else picked up on it!

        1. UKDancer*

          Me too. A diary is either something you write your secret thoughts in (like the diary of Anne Frank) or something you write your appointments in. The context indicates which in my experience.

          1. fhqwhgads*

            The distinction is in the US, “diary” is only used to mean the former, not the latter.

        2. micklethwaite*

          Yeah, Brit here and I agree – a diary can be a calendar OR where you write down your personal thoughts and what you’ve been doing. I would always say diary rather than journal for the latter.

          1. Pop*

            In the US, diary is typically only used for where you write down your personal thoughts, not a calendar. So as far as Americans are concerned, using diary to mean calendar IS a British term. I think that’s was Alison was getting at.

          1. Reba*

            We would call that kind of diary either diary or journal. We would never call a calendar or planner or appointment book a diary!

            Sounds like the word has dual usage in British English, but it needed to be clarified for US and other readers who don’t have both meanings for it.

            1. nonegiven*

              I think calendar would where I put an appointment to talk to HR about something or any other meetings.

              A journal would be where I keep work notes or maybe a list of things, just the facts, that happened that I want to take to HR.

              Diary would be where I put my emotions about what I was taking to HR. It would never leave my house.

          2. Archaeopteryx*

            The thing you write your thoughts and emotions in would be a diary or a journal in the US; some people just associate ‘diary’ with middle school girls so a lot more guys and adults tend to refer to it as a journal. The thing you write appointments and to do lists and what not in would be either your planner or your calendar.

          3. Carlie*

            I’m American, and I’ve only ever heard a diary as where your personal thoughts go. (a calendar is where the appointments go).
            To me personally, a journal is more for a specific purpose – such as an exercise journal, or a creative writing journal.

            1. londonedit*

              To me a calendar is a thing you hang on the wall, or maybe have on your desk (like one of those triangular cardboard desk calendars that stationery suppliers used to send out in ye olde days). You might write things on it, but it’s not a book. A diary is a book, where you’d write in your appointments and tasks and reminders for each day. You might talk of an assistant ‘managing the boss’s diary’ – meaning they manage her meetings and appointments. The other meaning of ‘diary’ is ‘personal journal’ but you wouldn’t have one of those at work.

              1. GothicBee*

                In the US most people would call that a planner. I think that’s what Alison meant, that if the LW was using “diary” to mean a planner/appointment book, then it’s not that weird for the boss to have it at work. But if the LW was using “diary” in the US sense to mean journal (i.e., place to write your personal thoughts, secrets, etc.) then it would be really weird to have that sitting out at work.

              2. Ask a Manager* Post author

                This seems to be the crux of the confusion (from all of us). In the U.S., calendar can hang on the wall or it can be a book you write appointments, etc. in.

        3. Chilipepper*

          I am confused because what all the Brits are saying here (a diary is place you write appointments or a record of private thoughts) is the same to me as what Alison wrote. Did she change it?

          She referred to the place you write appointments as a calendar and the place you write private thoughts as a journal. Is a calendar not what Brits use to write appointments in? Or is that kind of diary more like just a blank notebook with a list of appointments? I think her use of calendar and what I see y’all saying about a place to write appointments as consistent but if not, I likely need more details!

          1. londonedit*

            A calendar hangs on the wall. A diary is a book with space for each day of the week/month/year where you keep your appointments. It can also mean a personal journal.

            1. Formerly Ella Vader*

              And just to confuse things, nowadays schoolchildren in Canada (and maybe the USA?) are taught to fill in the dates their assignments are due in what I would call a datebook or planner and the schools call an agenda.

              To me, agenda is a one-page description of what’s going to happen in a meeting.

            2. Chilipepper*

              Ah, thank you. I could not grasp the nuance of a calendar hangs on the wall.
              I think it is fair to say that in the US, anything with dates on it is a calendar whether it hangs on the wall, sits flat in a desk blotter, sits in a sort of stand on the desk, is a notebook type thing you carry, or is in your computer, they are all calendars.
              A diary has dates but mostly has lined pages intended for writing lots of text and not so much for organizing your day.

              The Oxford dictionary shows the US and UK definitions:
              noun [ C ]
              /ˈkæl.ən.dɚ/ uk
              a printed table showing all the days, weeks, and months of the year:
              An old calendar for 2012 was still hanging on the wall of her office.
              a book with a separate space or page for each day, in which you write down your future arrangements, meetings, etc.:
              He wrote the date of the meeting in his calendar.

      3. Keymaster of Gozer*

        UK here and got a boss who’ll tell you to put a meeting in your diary (means Outlook calendar) and I also have a diary at home where I scrawl my general thoughts etc. (Not updated since January 2020). It’s one of those multiple use words we have here like ‘boot’ being: item of footwear, back bit of the car you keep stuff in and a way to remove some or something.

        Had a boss who only kept a written diary at work, refused to use Outlook to book meetings etc. He’d never had put personal notes about people in it though, that’s unprofessional.

      4. doreen*

        American here- and although I don’t use “diary” to mean a book with days of the week (I’d use “calendar” or “appointment book” , I’ve heard/read it often enough in the US that I’ve never thought the “calendar” meaning was a British usage. Although it could be a regional/occupational thing.

        1. WellRed*

          I just finished a British mystery and there was a desk diary of some importance. I definitely understood it to mean appointment book rather than personal journal.

          1. UKDancer*

            Was it a book set in the pre-digital era by any chance?

            A desk diary is a large diary / appointment book and in a classic crime novel it would probably be bound in leather and fairly weighty. They’re the sort of thing people used to use to record their appointments in. Very few people have them now I think because most of us use an online calendar instead. I have a Royal Ballet calendar hanging on the wall but that’s more because I like the pictures in it. I don’t know many people nowadays who use a desk diary rather than outlook calendar but some older people might.

            The type of diary people write their secret thoughts in is likely to be more like a notebook allowing for longer entries.

            1. 'Tis Me*

              I’ve used that sort of thing for task lists and deadlines? A bit like a homework diary but as an adult.

              Trello and Outlook do the same though and I’ve been digital a while :)

        2. Batgirl*

          British newsrooms very consistently call the appointment book “the diary”, as in “Put it in the diary” while most other nearby offices would say “put it on the calendar” or “book an appointment”. It might be an older term because newsrooms love to protect those.

    4. Caroline Bowman*

      Pissing about is very British! It’s a ruder version of ”let’s stop FANNYING ABAHT!” as immortalised in the Thin Blue Line.

      1. londonedit*

        I just want to say, on this most Tuesdayish of all January Tuesdays, thank you for putting the image of David Haig shouting ‘Stop FANNYING ABAHT’ into my head and raising a much-needed smile!

      2. BakerBaker*

        I was misreading the sentence due to confusing grammar/syntax–it read to me like the boss thought “she was pissed around,” of which I couldn’t begin to make heads or tails! No part of my brain could understand what it could mean to describe someone as “pissed around.”

        Once I realized it wasn’t an adjective, but a separate clause and verb, it finally made sense.

  8. SomehowIManage*

    5. In consulting it’s a common practice to check with clients before using their name, but many will be happy to allow it.

    1. Amlan Gupta*

      I would second this. I have done consulting for many years and I would never use a client name (even if public) without confirming with said client first.

      1. General von Klinkerhoffen*

        The very nicest clients will authorise a useful soundbite that you can use on your website/advertising materials.

    2. pleaset cheap rolls*

      I was going to say the same thing. The work products may be public, but the client being it OK with it being known that an outsider helped produce it is not the same thing. So if that’s not clear in the contract and you care about an ongoing relationship with the client, consider checking.

  9. MollyG*

    #4 Every state unemployment system had an appeals process, but the timeline is quite short. You need to quickly find when that deadline is and not miss it. In some states you don’t need to provide any more reason then “I don’t agree.” Then find a lawyer. Also check for non-profits that could help. I had an issue with unemployment and a local legal aid helped.

    1. Anon Today*

      This is true. However, due to “unprecedented times/volume”, that may not necessarily apply, depending on the state. But also, a legislative inquiry, again depending on the state, isn’t a guarantee of speed, although it definitely SHOULD get you some results. The unemployment system is not very efficient in many states, and was definitely not meant for this volume in ANY state. I promise we’re doing our best, but yep, it’s a mess.

        1. Anonapots*

          That’s not necessarily true due to the backlog. People in my state were getting denial letters after the window had closed and the Unemployment Agency was being a bit more flexible because the delays were their fault, not the fault of the people applying. 2020 was not a normal year so a lot of the normal rules do not apply. Better to explore with the agency rather than just assume it’s too late.

    2. BlueWolf*

      When my fiancé had an issue with his monetary determination in Virginia he tried to file an appeal through their online system but the document attachment part wasn’t working. He submitted online anyways, but also sent a written appeal by certified mail so that he had proof they received it by the deadline. Of course they took about two months to process it, but they did eventually get to it. It wasn’t clear from the letter if there is an appeal option, but I would think there should be, especially when they are demanding repayment of thousands of dollars.

  10. Zoe*

    OP #1 you just have to gauge whether the risk is worth it. If the worst happened, she was aghast/offended/embarassed and you weren’t friends anymore, is that worth the risk to you? Three years is a long time to have a “crush” so if it was me, I’d probably give in at some point just to know. Does she date?

    1. Roci*

      Yeah, that’s the problem with long crushes. Is this the kind of thing where, after one of your night hikes, you can say, “Hey, I really like spending time with you. Would you be interested in going on a date?” and if she says no or seems uncomfortable, you can say, “If not, no worries, I’m happy to just be friends with you” and otherwise treat her warmly and respectfully? If you’re in too deep to brush it off, then you’ll have to decide whether you’re willing to risk it all–that’s an age-old question.

      Not knowing anything about the two people involved, I have to say that in my early 30s I would be very cautious about flirting/encouraging a minor or someone barely a legal adult. So it’s possible that she may return your feelings now, but it would be inappropriate-to-iffy for her to have liked you as long as you have liked her. No matter how mature and intelligent you are/were, she should be and should have been aware of that dynamic.

      1. Mx*

        But the fact is he’s not a minor. He could have started this relationship 3 years ago. If 21 years old was too young to have a relationship, then majority would be later.
        One of my most beautiful love story was when I was 19 and my partner was 42. It’s a great memory.
        The only bad memories were people around criticising, but since I was female and he was male it wasn’t as intense as the reverse.

        1. Richard Hershberger*

          I had a thing with about the same ages as in the LW’s case, with me the younger half. In retrospect, I am surprised that she was interested in an awkward and geeky kid, but at the time I was delighted. It was very educational, and this education has served me well. But probably the key fact is that neither of us saw this as a permanent thing, and we were both open about this.

        2. Blisskrieg*

          I was hoping someone would share some age-difference success stories! I wanted to chime in with mine. 20 to 21 year difference (depending on time of the year) between me and my husband. We are near our 24th anniversary, and closer than ever.

          I was blessed that upon meeting him, my parents only expressed that we were very well suited, and welcomed him with open arms. I will always remember that they withheld their judgment as a measure of trust in my decisions, and the difference that made to our family. However, I do remember raised eyebrows sometimes for several years when we were out socially.

          I agree with Mx. I am female and he is male, and that makes things easier. It does seem like that is changing as well–more couples with the woman being older, so hopefully the way is easier for the OP than several years ago.

          1. Chinook*

            I have 9 year age difference with DH and we met when he turned 21, but we are from two two distinct generations when it comes to cultural experience. Sometimes I have more in common with my MIL than him, which is weird.

            What I have learned is that 21 is an age where there is still a little more maturation than can take place that can lead to change in what you want. DH is also an old soul too but he did change from 21 to late twenties, hich caused us major problems that led to a couple of separations. At 21, he was convinced we were what he eanted and in his mid-30’s he feels that way again, but in between there were times when he saw what his peers were doing and he felt like he was missing out.

            That being said, you have to ask yourself if risking your friendship and job mentor is worth the risk. There is no going back when you cross the line to expressing romantic feelings. I recommend caution only becuse good friends are hard to find. And, if you do play it safe and she has similar feelings, there is nothing stopping her from letting you know.

          2. Lilliputin*

            I have a 27 year difference with my wife (I’m female) and we are now going on 21 years together. She took me out for my 21st birthday!

            We were both on the rebound from breakups (my 3 years, hers 13) and called it a summer fling. We got along like a house on fire and enjoyed each others company, so why not! We were having fun and didn’t take it all too seriously.

            The age was only an issue because we were never prepared to commit, because it couldn’t possibly last, and as years went by we kept waiting for something to happen. A few years ago we gave in and got married. We’re still as happy as ever.

            Take it one day at a time and if it makes you happy and isn’t hurting anyone, who cares! It’s no one else’s business and sometimes, things just work.

        3. LTL*

          Just because an age gap wasn’t an issue for some people, and some were unfairly criticized (at a certain point, you have to realized that your loved one has made their own choice, and if you don’t even know them, don’t comment in the first place), it doesn’t mean that it’s not a yellow flag. It’s just not a red one.

          I’m very happy that you found your partner and that you’re happy together. But the fact is that in many relationships between a teenager and someone who is middle aged, the older party is with the younger one for a reason. And “but they’re not a minor” is a common argument made by people with bad intentions. There are ways to tell the dangerous relationships from the healthy ones, but let’s please not pretend that we shouldn’t flag the age gap because he’s not a minor.

          “There are some very happy relationships with large age gaps” and “be very mindful of large age gaps in relationships” are two statements that can coexist. It seems that whenever someone brings up the latter, people come out to say the former.

          Roci is correct that the woman in the letter should be aware of the dynamic and cautious at the very least. That’s different from saying it’s an absolute no-go.

          1. Blisskrieg*


            I agree with your statement: “There are some very happy relationships with large age gaps” and “be very mindful of large age gaps in relationships” are two statements that can coexist. It seems that whenever someone brings up the latter, people come out to say the former.” However, people typically come out to say the former because any discussion difference in age groups often comes from a highly critical perspective. It is reasonable for people to share their positive experiences in response. I don’t believe pointing out that there are positive outcomes means that the issue shouldn’t be flagged as a consideration or concern. Anyone entering a relationship needs to explore their motivations and the potential motivations of their partner, and when there is an age difference, that certainly is one of the aspects that should be explored. We agree that the two statements can coexist.

            1. Paris Geller*

              Agreed. Those two statements definitely can coexist, and I agree that age gaps can be a yellow or red flag, depending on the ages involved. I just think those of us in larger age gap relationships (which. . . what even is considered a large age gap? There are 11 years between my partner and I. I consider that a large age gap, but I’ve had people who think it isn’t and people who think it is. I think we can all agree 21 and 36 is a large age gap, but anything around the 9-12 year mark often seems to be iffy territory. A medium age gap?) do tend to want to point out the former because like Blisskrieg said, many people are very critical.

              I do think most people agree that age gaps matter less as you get older. At 29, I can’t imagine dating a 21 year old, but my partner is 40. However, we’re both basically in the same stage of life–never married, no kids working professionals who have similar professional and personal goals and values. And it is odd how some age gaps are perceived. Being 29 and dating a 40 year old sounds like a much larger age gap because I’m still in the my 20’s and my partner his entered his 40’s, but we both will have birthdays in May and I’ll turn 30 an he’ll turn 41. Same gap, but I feel it won’t be perceived nearly the same way it is now.

        4. Roci*

          I would have said the same thing to you and your partner, and anyone in a similar situation where one is barely a legal adult and one is over 35. There are many people who date younger people for predatory or inappropriate reasons, and the young people don’t always have the life experience to identify the warning signs. I do not doubt that many people–like you who have shared here–have a wonderful love story with a large age gap, but it is necessary to keep the power dynamics in mind.

          3 years ago OP may have been legally a minor at 17 years 10 months or something. Or where I live the age of majority is 20. Either way “technically it’s not illegal!” is not a convincing excuse for a grown man or woman to date a younger person. And “well I’m mature so it’s OK!” is not convincing to hear from OP either.

      2. RebelwithMouseyHair*

        This is a blog about work, not personal relationships, so I don’t know that we should be commenting on the age gap at all. Asking a woman out that you work with can be fraught enough without that aspect. The difference in seniority could exist without the age gap after all.
        And hey, this woman goes on night hikes with him… how many people (let alone colleagues) would anyone night hike with while having zero romantic interest in them? As a het woman I’m pretty sure I’d never night-hike alone with a man unless I was interested in him.
        And at 21, this guy is not necessarily looking for a long-term relationship. He might be happy with just a fling, before realising that they do have incompatibility problems (which would not necessarily be related to the age gap either).

        1. Blarg*

          I think the age matters for context of their relationship. It seems she’s always been in a managerial/supervisory role since he’s been with the company. She hired and worked with him essentially as a kid. She may well see him as a quasi-mentee/little brother.

          Night hiking is quite common in some places so not sure that is an indicator of much beyond shared interest and weird retail hours.

          Lastly, though: young people, even those who say they are mature, are rarely subtle. The likelihood that a woman in her 30s doesn’t know that a man in his early 20s has been into her for three years is …. small. See also: everyone who works at her current location, where he just hangs out off the clock during a pandemic to see her.

        2. MK*

          Hmm, I don’t think it’s safe to draw conclusions from the night hikes, different people have different boundaries. Also, in this year of the plague, I would be even more hesitant to put much importance to… well, anything really. People are starved for human interaction, they reach out to people they haven’t spoken to in years,etc..

        3. Catherine*

          I’d never night hike with someone unless I was sure our relationship was platonic! The last thing I want is to be out alone in the dark woods with someone who’s going to throw feelings at me.

          1. Quill*

            Ergh yes! I’ve had enough awkward encounters in the daylight that having one in the woods at night holds no appeal.

        4. Middle Aged Woman*

          I would ONLY night hike with people I felt confident were not romantically or sexually interested in me! I’m not going out there with anyone who I think could potentially have reasons to hit on me while I’m in a remote location when I have no idea how they will take rejection! Hell no!

          I would think it more likely that the older colleague views the OP as a nice kid with a common interest who she’s happy to hang out with, but who she thinks is clearly not a romantic prospect and thus she is comfortable with these interactions in a way that she would probably not be if she considered he was likely to think of her that way.

              1. Anonapots*

                I don’t get this comment. Single people hook up. Night hikes with someone you’re romantically interested in are not…weird. They’re also normal for people you aren’t romantically interested in, or people you’re already romantically interested in. In other words, night hikes don’t really indicate anything as far as feelings go.

          1. a sound engineer*

            I wouldn’t read much into the night hikes, personally – I spend one-on-one time with lots of male friends/coworkers (at all times of day) with absolutely no romantic interest on either side.

        5. Batgirl*

          It’s pertinent because asking out someone older and senior at his age could reflect on her opinion of his judgement. We do get judged by our soft skills at work and this is something that could unfairly look like naivety about life stages and reading others even if it’s just a reasonable miscalculation. Personally, the night hikes would be a clear ‘go ahead’ signal if it was coming from me. Yet there’re lots of women who would be stunned that a friendly activity would be misread that way. There are people who think dating a 21 year old is nuts when you’re in your mid thirties/A 21 year old wouldn’t be interested anyway, so clearly all activities are platonic! Other people think: “Why not? Let’s date?” The only way the OP can know which reaction he’ll get is to ask and unfortunately, it’s a risk. Getting to know her and her thoughts on things in general, very well may help.

        6. Elspeth McGillicuddy*

          I don’t think the night hikes say much about the possibility of romantic interest. However, they do say a lot about how much she trusts and is comfortable with him. As a woman, you don’t go off alone in the woods at night with someone unless you are sure they aren’t going to harm you. That trust and comfort might not be quite so strong after he hits on her.

          Something to think about when measuring the pros and cons.

          1. Anonapots*

            This is really the key. She feels comfortable enough with him to go on these hikes and that can shift if she isn’t reciprocating romantic feelings. OP should ponder if he’s willing to give up the relationship entirely if she doesn’t feel the same way.

        7. Blisskrieg*

          I agree with RebelwithMouseyHair that today took a detour into personal-relationship advice, rather than just work advice. I think the age difference needed to be explored because it was brought up by the OP, and it can play into the power dynamics, but the advice itself became more about relationships than work. I shared my age-difference relationship success story above to provide a counterbalance, but I agree that in general, the column took a a detour today that took us out of the work realm.

        8. Delta Delta*

          I used to go on night hikes with people from work. It worked out that way for a couple reasons: 1. Night was when we weren’t at work and had time for exercise; 2. There was an excellent park with trails very close by, which was safe and available for hiking; 3. We all lived in the same general geographic area; 4. The hikes often ended up being about an hour long and were a good way to stretch legs and gab about work and the world. Because of my personal night-hike-with-coworkers background, this doesn’t feel especially off for me, since it’s possible these folks have a similar situation.

          I’d also say let the crush go and enjoy the hikes and conversations.

        9. Ed Anon*

          Huh! It’s interesting to me to hear that there are so many cultural differences with the reading of “late night hikes.” Also, to me, late night = midnight or later, so I was reading this as her going for hikes with him at 12/1 in the morning.

          It’s also interesting to me that the fact that she’s a woman seems to override the fact that she’s older with institutional authority over him — i.e., she’s going for late night hikes with him because maybe she feels safe with him, whereas I absolutely could not picture commenters feeling the same way about a 36-year-old man doing this to a 21-year-old woman.

          1. Clisby*

            Heck, I worked for years at newspapers, where I didn’t get off work until midnight. If I wanted to take an after-work hike with somebody, it would have been around midnight or 1. When you’re used to working 2nd shift, there’s nothing special about going out to do things (go to a bar, go out to eat, go on a hike …) after midnight.

          2. Filosofickle*

            I agree! To me night also means something like midnight, or at least after 9p because before that would be “evening hike”. Or it means “after dark”.

            I’m weirdly hung up on the logistics of what’s meant by night hikes in this convo! We hike lots here in California , but only in daylight and pretty much all our trails and parks close when the sun goes down.

        10. 'Tis Me*

          It would be possible to be interested in potentially dating somebody and being open to romance with them but wanting to explore that transition really slowly. Not go from friends to them potentially (and I’m not saying the LW would) suddenly turning into a grabby handsy octopus in a deserted area alone with them at night (“but you said you were interested! What do you mean ‘no’? This is what we were talking about and we both know it so there’s no reason to be coy now!”).

          Definitely a phonecall/text discussion rather than one to spring in a “romantic” (isolated) spot!

    2. Grits McGee*

      Another risk of asking is that she could scale the friendship waaay back out of concern for optics and professional reputation. Knowing that OP has romantic interest might make change her perception of their working and non-working relationship, and what it might look like from the outside. (Even if she returns OPs feelings)

    3. RagingADHD*

      Or if she just says “no thank you” and LW just feels too awkward or hurt to continue being friends.

      Unless they are both extremely good at compartmentalizing, making the attempt is pretty likely to irrevocably change or end the friendship, so it’s best to be prepared for that.

  11. Ed Anon*

    Does no one else feel that the authority and age differential in LW1 is problematic at all? If I’m reading correctly, she started out in a position of authority over him – and that influence can carry over even if he technically doesn’t report to her anymore. And given that, especially if he is still in her chain of command, I can’t help but side eye the fact that a 36-year-old woman would be regularly going on late night hikes with a 21-year-old that they’ve developed such an involved friendship with without considering at least the optics of that.

    I can’t help but feel that if the genders were reversed, I would be sketched out by this. And yes, statistically that would be much more well-founded — but it still remains that it can be hard to identify when you’re young how much of your feelings come from a power/influence differential (whereas the one with more influence should be well aware of that).

    1. Chriama*

      I agree. Alison flagged the age difference but honestly I’m reminded of one of our old letters where the OP was in HR and flirting with a student intern. At 21, you’re flattered by the attention. At 36, you should know better.

      1. Ed Anon*

        Yes, thank you. I should also add to my comment that the implications for advice for the OP are that – I don’t think what the assistant manager is doing is entirely appropriate, ESPECIALLY if he is still in her chain of command.

        Realizing that what the OP welcomes as close friendship / possible flirtatious behavior (the late night walks) might actually be inappropriate behavior on the part of someone who has enough influence and authority to know better should most definitely change the situation and whether they consider acting on their crush or not. (As well as fine tuning how they evaluate similar situations in the future!)

        But if I’m off base and what the 36-year-old is doing is totally appropriate, then don’t mind me.

      2. Clisby*

        But there’s no indication (that I see) that this woman is flirting with the LW. As Alison notes, he’s said nothing that indicates that she has any romantic interest in him. At least based on what LW1 has said, this is way different from the situation with the 18-year-old intern and the 40ish woman.

    2. Jenny*

      I flagged the statement in detail below, but what really bothered me was also that the LW was using language that’s typical for an exploitative relationship (roughly, “but it’s different because I’m mature for my age”).

      1. Emmanuel Macron*

        Quinze ans n’est rien!

        Though I’ve never actually heard someone say “I’m mature for my age” and actually be mature.

        1. General von Klinkerhoffen*

          The way I look at age gap relationships is to start counting from adulthood. LW is therefore 3 and NightHiker is 18. She has six times as much experience of adulthood as he has.

          I’m basically her age and have friends his age but if any of them declared a romantic interest I’d be squicked out immediately. It’s a completely different context.

          1. Richard Hershberger*

            Back in the day, the rule I learned was take the older person, halve their age and add seven. This gave the minimum age for the younger than would not raise eyebrows. So at 36, the younger limit is 25. That being said, that was more for serious relationships than for flings. Also the question about the relevance of raised eyebrows.

        2. Keymaster of Gozer*

          I used to say I’m mature for my age at 20. Now I’m in my 40s, realise I know absolutely bugger all in general and have an exceptionally immature sense of humour.

          So if I’d wanted, back then, to claim I was mature I should have been a lot less arrogant (gods was I obnoxious), a lot more willing to laugh and a lot less sure that I was grown up. Because I’m still giggling over my nephew’s fart jokes 6 days later…

          1. Batgirl*

            This does not apply to OP, who is an established adult, but I used to teach newly adult students, (18) some of whom I’d taught at an earlier stage. They’d say they could date more established adults because they were mature. Because a lot if them were high achieving types, I’d say “Big deal. You were mature when you 12! You’re delightful company, responsible and emotionally intelligent. That doesn’t make any difference though.”
            They’d splutter something like ‘what else is there?’ because their focus had always been on this.
            I’d say “Experience and power. Who has more money and resources? Who’s been paying rent longer? Who has a car? Who’s lived with someone before? Severed ties with an ex who wouldn’t go away? Had their heart broken multiple times?, Who’s more likely to take the lead in a crisis or overrule the other?” It’s navigating the messy stuff that only experience teaches you; maturity and common sense can only teach you how things should be.

            1. Shirley Keeldar*

              Very wise comment! OP, do please read and take note. And the supervisor/employee angle adds yet another layer of power dynamics.

            2. 'Tis Me*

              I think this may be the best summary of the pertinent issues I’ve ever seen! And what a great explanation that totally encompasses that this isn’t anything about *them personally* – you agree that they are lovely, but that’s completely beside the issue: they are not on your radar “like that” and don’t belong there <3

        1. Quill*

          Academically? Sure I was. In terms of handling childhood responsibilities? Yep, because oldest child.

          Was I mature for my age in ways that had anything to do with adult responsibilities? Duck no.

      2. Batgirl*

        I didn’t like that either. The focus was on “how I present to others” which is a pretty typical and natural priority when you’re young and wanting to make an impression.
        But when you’re making romantic decisions you need to park public opinion and think about what’s good for you. I would never dream of dating someone younger and junior because the power differential would put them at such a disadvantage.

      3. merp*

        This is also what jumps out to me. Without more information, I don’t know whether or not the older coworker is deliberately making him feel that way or not, but regardless, it doesn’t seem like he has the healthiest viewpoint toward this relationship (in the sense of what’s best for him). That’s not workplace advice anymore really, but between that and the fact that she is his superior at work, I don’t think he shouldn’t say anything.

    3. Purple State*

      This is absolutely a case where, if the genders were reversed, the commenters would be up in arms. Everyone seems to be pointing out that LW is 21. But this started when he was 17 – a minor, likely still in high school, and the other party was his manager at the time. While she may no longer be his manager, she is a manager in the same organization that employs the LW. Frankly, she sounds rather predatory to me.

      1. Colette*

        She has done nothing, though (except treat the OP like a friend) – why would she be predatory?

        1. UKDancer*

          I can’t see anything predatory. They’ve gone for walks and chatted. I don’t consider that predatory. If anything it strikes me she’d view the OP as more of a kid brother because it’s the sort of thing one does with platonic friends in my experience. If it were a romantic candlelit dinner, that would be romantic. A walk at night is more something you do with people who are “safe.”

        2. Purple State*

          But she wasn’t his friend, she was his manager. He was a seventeen year old kid working in a retail clothing store. Why would she be having “deep, intellectual conversations” with him? Why would their conversation go beyond “put the red shirts next to the blue shirts”? She likely saw him as a young kid, slightly full of himself (“I’m not your typical . . .”) and took advantage of the situation.

          1. EventPlannerGal*

            Given that this is all coming through the lens of a 21yo with a crush who thinks he’s ‘mature for his age’ I am pretty certain that these conversations were probably not Plato’s Symposium. In retail there are often quiet periods where you end up chatting total crap with your coworkers for something to do while stacking shirts. I agree that it’s totally possible that someone could take advantage of that dynamic but I don’t really see how she has at this stage – to me this just really reads like a very young person with a crush hyping up normal interactions.

            1. There’s probably a cat meme to describe it*

              This. What you consider “deep intellectual conversation” is usually very different at 36 versus 21.

              I am also struggling with the insinuation that every conversation a female colleague has with a male coworker beyond shirt-stacking instructions could somehow be misread as sexual interest.

              1. Clisby*

                Or even if the genders were reversed – surely 21-year-olds and 36-year-olds can have interesting conversations. When I was 21, I thoroughly enjoyed talking to older people – they were often were talking about something I had no experience with. (And for all I know, they were entertained by talking to me, since my lived experience was way different from what they experienced growing up.)

                1. UKDancer*

                  Definitely. When I was a student I worked as a tour guide at a castle and was often on duty with a much older chap who had been in the navy. I really enjoyed chatting to him as he had some amazing stories about his experiences in the military. He seemed to like my stories of student life. Being a tour guide involved quite a bit of waiting around between tours and so we had some nice conversations. There was no romantic interest on either side, we just enjoyed talking together.

            2. I Wrote This in the Bathroom*

              Probably something about a book, a movie, or a board game they both liked, as opposed to the “I got sooo high last night, herp derp” he was possibly getting from his age peers.

            3. 'Tis Me*

              Yeah, when I was 16 or 17 the assistant manager (probably mid-20s, maybe later 20s? Male) and I had been chatting in a quiet time and I’d ended up doubled over laughing, then a customer came in so I tried to get myself under control. I nearly managed, but half-way through serving him, the giggles came back and I ended up collapsed on the counter HOWLING and the assistant manager needed to take over.

              But, y’know, retail. It was fine.

              Also completely platonic and I would have been horrified and disturbed had he indicated he saw it as more than a colleagues who get on thing.

          2. Colette*

            People talk to their coworkers, and not always about work. That doesn’t mean anything more than that they are stuck in the same place on a regular basis.

          3. Littorally*

            Now that’s silly. Are you one of those people who thinks that minors should never speak to an adult that’s not related to them? She did not do anything wrong by talking with her coworker.

            I had some fascinating discussions with my older coworkers when I worked retail. Most of the shop employees were retired — if I had only been able to have conversations beyond the immediate need with people in my own age bracket, there would have only been one other person I could have conversed with! Instead, I got to hear cool stories about how my boss had run away to join the circus as a teenager, some fantastic historical discussions with a guy who traveled all over the region to do historical reenactments, and so forth. Were they being predatory or taking advantage of the situation because I was interested in their life experiences?

            1. Chinook*

              This. Friendships happen regardless of age. In fact, it is healthy to interact with people across generations and it exposes both parties to different experiences and ideas. And friendships evolve naturally. Least worrisome part of this is the friendship that evolved over 3 years of working together, especially in retail, where there is a lot of turnover and downtime, so the familiarity can create friends.

            2. Something Something Whomp Whomp*

              Yes. That sentiment was confusing and odd – even if their age gap is potentially awkward from a romantic perspective, that wouldn’t necessarily mean that they wouldn’t have anything to talk about beyond small talk. People’s lives don’t need to be in lockstep for them to be able to develop friendships.

            3. Jennifer*

              This I agree with. I think having friends of varying ages is healthy and it’s perfectly normal to talk to your coworkers during downtime at work, regardless of how old they are. Those aren’t the things weirding me out about this friendship.

          4. tinybutfierce*

            Do you never have non-work conversations with your coworkers you’re stuck with 8+ hours a day? Retail throws all sorts of folks who might otherwise never interact together, there will be times the store is dead and there’s nothing work related to talk about, so you talk about other stuff (which might include whatever a 17-21 year old considers “deep, intellectual” talk). There’s nothing in this two-paragraph letter to indicate she’s somehow taking advantage of him.

          5. Yorick*

            Maybe she likes to have conversations with young coworkers to help them develop professionally. It sounds to me like she’s modeling work friendships. I’m not sure about the night hikes, but that could be perfectly appropriate too.

            If a woman had written in about a male manager, I wouldn’t assume he was a creep, because I don’t see any grooming behavior in the letter – just friendly behavior between a manager and their employee.

          6. annalisakarenina*

            To be fair, when I ended things with a romantic interest, he said he thought we were great together because we had “deep and intellectual conversation”. Really, we just had easy rapport and he interpreted it as more.

            I really think LW1 is viewing all of their interactions through crush goggles and making more of what is there.

      2. I Wrote This in the Bathroom*

        This is absolutely a case where, if the genders were reversed, the commenters would be up in arms.

        And if she was 85 and a billionaire, the commenters would think he is after her inheritance. But she is not, and the genders are not reversed.

        But this started when he was 17

        What’s “this”? Them talking?

        1. LTL*

          There are cases where reversed gender matters because of the dynamics in our society. Potential abuse and exploitation isn’t one of them.

          I don’t think that LW’s coworker is predatory. IMO we don’t have enough information to make a judgement on that, though I’m glad that some commentators flagged some of the language in the letter. But this particular case isn’t one where gender matters.

        2. Clisby*

          Even if the genders were reversed, the story would be:

          1) 21-year-old woman has crush on 36-year-old man.
          2) They’ve known each other, as colleagues, for 3 years and apparently have a warm, friendly relationship.
          3) No evidence whatsoever that this man has anything other than a platonic interest in her.
          4) Even so, she wants to ask him out.

        3. a sound engineer*

          Even with genders reversed, it doesn’t automatically mean anything shady is going on. I work in an extremely male-dominated environment, I started in the industry before leaving high school. Pretty much everyone I worked with minimum 10 years older than me and it was a rare day if there was another woman working with me. We still had non-work related conversations when not much was going on and they were just…normal conversations about our lives, or whatever else was going on at the time.

          From what was said in the letter, I don’t think any of the behavior has crossed over into predatory. I get why the wording of the letter-writer is a flag, but I also knew a lot of people in college with the same attitude of “I am more mature/deep/intellectual than my peers”, and often they were conflating academic maturity or just how they came across in conversation with truly being mature across the board (emotionally, in relationships, etc)

      3. Georgina Fredrika*

        Your math is off – 21 minus 3 is 18.

        I also think retail is a context that DOES matter here. Considering everything they’ve done is platonic – it’s way more common in retail (and restaurants) than in an office for people to be friendlier with their co-workers. My retail/restaurant friends frequently make a lot of friends in their industry because they do activities together all the time- often b/c they’re not on the same 9/5 sched. as the rest of us. And when I worked in food service I talked WAY more to my coworkers than I do in an office.

        Nothing she’s done is predatory unless the OP is withholding info. I guess I could see why you’re red-flagging “deep, intellectual discussions” but that’s OP’s wording, and OP is a very young adult. I think what could be a normal convo for her is potentially impressive to someone whose peers are still at a different mentality/life stage.

      4. Beth*

        I think this is an over-read. All we know about her is that she’s 15 years older than him, that they have had intellectual conversations over the 3+ years they’ve known each other through work, and that now that they’re in the same area and she’s no longer his supervisor, they’re friendly enough to go for walks together sometimes. None of those are inappropriate. OP has a crush, but I don’t see anything to suggest she’s manipulated him into it, encouraged it, or even been aware of it.

    4. Cat Tree*

      The age difference isn’t ideal, but honestly I didn’t get the sense that the older coworker is interested at all. The young person is the one who wrote in, and it’s super common for people of any gender at that age to have a crush on an older, more mature role model. These crushes usually aren’t reciprocated. So if a 21 year old woman wrote in about a crush on an older man I wouldn’t automatically be bothered by that, unless there was some indication that he was flirting back.

      Now, if the older coworker wrote in my feelings would be different. But I’ve been reading through the archives and the advice is what you would expect even for women. There was one about a woman in HR flirting Auth a young-but-legal male student working, and everyone was rightly horrified.

      This letter feels more like a mentoring thing or just a friendship. I would hate to discourage mentoring or friendship based on gender just because the younger person develops a perfectly normal crush sometimes. As long as the older person handles it appropriately (which is usually the case) it’s a good chance for the younger person to learn that you can have feelings but not act on them. Let’s give people some credit until we have a reason not to.

      1. Yorick*

        LW might just be experiencing a version of transference, where you start to have romantic feelings toward a supportive mentor.

    5. I Wrote This in the Bathroom*

      For all we know, she’s going on late-night hikes with OP because she likes hikes, cannot go during the day, is not feeling safe to go alone at night (as would I), and thinks that OP is the safest male companion she can come up with, because what are the odds of anything romantic happening between her and a 21-year-old? I fail to see it as a predatory move on her part.

      1. Clisby*

        That’s pretty much how I saw it. When I was 36, 21-year-olds were kids. It would have taken a truly extraordinary 21-year-old to pique my interest in anything beyond a platonic relationship.

        1. Quill*

          Heck I’m 28 and 21 year olds are kids. Made a joking remark the other day to an aquaintance about how they’re too young to remember (insert historical event here) and was rewarded with a “i HAVE PAID TAXES FOR FOUR WHOLE YEARS”

        2. UKDancer*

          Goodness yes. I am about 40 and have colleagues in their 20s and there’s no way I’d consider them possible romantic attachments. They’re so young.

        3. Yorick*

          I’m 36 and I would have zero interest in dating the vast majority of 21-year-olds. They even still kinda look like teenagers, not to mention the difference in maturity and life experience.

      2. There’s probably a cat meme to describe it*

        As a 30’s woman, this explanation was the first obvious thing I thought of too. She clearly sees him as “safe”, but that could be very independent to sexual interest.
        And OP, if you do decide to ask her out, for the love of crème brûlée, do not do it during one of these night hikes. If she’s hiking with you platonically because feels vulnerable out there but safe with you, and then you unexpectedly pull a move out there, away from people, in the dark? Eeeesh, don’t.

      3. Jennifer*

        But I asked myself if I would feel the same way if it was a male 36-year-old manager asking a 21 year old entry level employee to go on a late night hike, and honestly I wouldn’t. I would tell the younger employee to stop going hiking. It’s fine for them to have a friendly working relationship, but I’m getting the icks from this.

        1. Yorick*

          I might give that advice if the manager seemed to be interested or otherwise off, but not necessarily.

        2. Clisby*

          What would be your advice if the 21-year-old asked the 36-year-old to go on a hike? LW says nothing to indicate who suggested night hikes.

          1. Jennifer*

            The same as it would be if a student asked their teacher to go on a night hike. Just because the younger person initiates the relationship doesn’t mean that the older person shouldn’t set boundaries.

            1. TechWorker*

              Student – teacher is not quite the same as employees of different ages though, not sure that’s a helpful comparison.

    6. Mel_05*

      Yeah, I would definitely be giving this more of a side eye if the genders were reversed. I honestly do still kinda question this woman’s judgement.

  12. JM in England*

    Re #3

    At OldJob quite a few years ago, the director’s 9 y o son died suddenly on Christmas day. When I returned from the Christmas break that year, my line manager told myself and the rest of the team about this and we told not to ask the director about how his Christmas went.

    1. EvilQueenRegina*

      Christmas 2012 when I was in my previous job, my aunt had surgery for a brain tumour right before Christmas and at about the same time my grandad (who was effectively the father figure in my life since about 1992 as my dad wasn’t really around) had been taken very ill and was in hospital, getting a dementia diagnosis and there were other serious medical issues at the time.

      This had been going on pretty much throughout December, and my immediate team knew the situation and so didn’t word any questions about Christmas in quite that way (the closest friend I had in that job, who is still a close friend now, did tell me that it was okay to just be honest with her and say if things were crap). It did come up where people from other teams who I knew less well and who didn’t know the situation would ask me how my Christmas went, but I knew it was just a being polite thing so pretty much followed the equivalent of Alison’s script and basically said it was okay and then changed the subject.

    2. DinoGirl*

      This is along what the letter raised for me. My mother was hospitalized due to a recent severe cancer diagnosis over Christmas. I don’t want to over share with my boss or co-workers, but it also seems relevant for people to be aware when you’re experiencing something devastating in your home life, no? But I’ve erred on the side of being vague/deflecting “how was Christmas?” Questions for now.

  13. Dennis Feinstein*

    It’s Aussie or British.
    It basically means the boss thinks she just messes around at work doing not much or pretending to seem busy.

    1. Dennis Feinstein*

      Sorry this was meant to be a reply to the commenter who wasn’t sure what “pissed around” meant.

  14. justcourt*

    LW#4: (I’m assuming you live in the US)

    I used to work at a state agency that handled state and federal complaints of employment discrimination (whether your state is authorized to handle federal complaints will depend on your state discrimination laws and whether the EEOC has allowed it), and I saw so many people with discrimination complaints being handled by attorneys when the complainant was perfectly capable of handling his or her own complaint. Most cases of employment discrimination aren’t that complicated, settle out of court, and aren’t worth very much money. And a lawyer is going to take a cut of whatever settlement or judgment you receive.

    If you believe you’ve been discriminated against on the basis of a disability or perceived disability, I recommend contacting your state agency (state agencies generally process complaints a lot faster than the EEOC). The name will probably be something like [State] Human Rights Commission or [State] Commission on Human Rights. They will be able to answer questions about the complaint process, whether they are authorized to handle EEOC complaints, whether your employer is covered by state (or federal) discrimination laws, etc. They can also help you file a complaint. What they can’t do is represent you or give you actual legal advice.

    If you decided your case is too complicated or it goes to court (laws generally require complaints to first be investigated or adjudicated by an administrative agency before going to court), you can always hire or consult with an attorney.

    If this doesn’t apply to you, good luck and I hope someone might find this useful. I am also happy to answer general questions about the process and direct you to your state agency. I just can’t answer questions about your specific case.

    1. MK*

      Consider the fact that if you are someone working in an agency handling employment complaints, your perception of what the average person is “perfectly capable” to handle is likely not accurate. It’s very possible that handling such a case doesn’t really require a law degree, but it highly improbable that the average person is equipped to deal with it easily, at least without doing a ton of work to educate themselves about regulations and procedures.

      1. Insert Clever Name Here*

        And on top of that, there are many things that I’m perfectly capable of handling but that I decide to leave to other people when the stakes are high. In something like LW’s scenario, I would absolutely use a lawyer because if I’m denied, I’ll spend the rest of my life going “was it something I missed that a lawyer who’s done this 78 times wouldn’t have missed?”

      2. justcourt*

        I can’t speak to every state, but administrative complaints, investigations, hearings, etc. are very different from court. It isn’t necessary for a complainant to have in depth knowledge of rules and procedure.

        Here’s a general overview of the process:

        – The complainant submits a complaint either through an attorney, on their own, or with the help of agency staff.
        – The complaint is sent to the defendant, who has a certain amount of time to respond to the complaint.
        – agency staff conduct an investigation, including speaking to the complainant, the defendant, witnesses, employment records, etc.
        *Legal challenges to the complaint (e.g. a motion to dismiss based on lack of jurisdiction because of the number of employees) is handled by the agency.
        -during the course of the investigation, the parties are encouraged to reach a settlement (e.g. through mediation, settlement conference, etc.), and the agency can even help facilitate a settlement
        – the agency issues a report finding probable cause or no probable cause
        -depending on the outcome of the report and state law, the complaint can be heard by the agency (essentially a trial within the agency); be settled; proceed to an actual court; be dropped by the complainant

        *the order might vary slightly from state to state or from the EEOC. For example, I believe the EEOC conducts an investigation before taking a complaint, but my state filed the complaint first.

        There can be benefits to having an attorney (e.g. an attorney is going to have a lot more experience with settlement negotiations), and they are pretty much required for an actual court trial. However, a complaint with an administrative agency is much more user friendly and a lot of complainants didn’t have representation, particularly when they worked lower paying jobs where any settlement or judgment was unlikely to exceed a few thousand dollars.

        1. L.H. Puttgrass*

          I think you underestimate how much that process can be intimidating to someone who is not familiar with it.

          It’s been ages since I did anything UI related (mumblemumble years ago, in a law school), but it’s not at all easy fighting an employer who has lied about the reason for a termination. Even if it never gets to court or a hearing, just having someone to guide them through the process can be tremendously helpful.

          1. justcourt*

            I’m not talking about UI. I’m talking about a discrimination claim. LW said he/she was fired after submitting requests off for life-saving surgery, and his/her employer gave multiple reasons for the firing.

            I don’t know about LW’s medical condition, but I think it might be worth it for him/her to consider whether their medical condition constitutes a disability (or whether their employer perceived it as a disability) and if the firing was due to discrimination. I thought that was what AAM was suggesting when she recommended consulting with an attorney (in addition to possible UI issues).

            I just wanted to give my perspective on whether attorney representation is necessary if there’s a discrimination claim.

            1. L.H. Puttgrass*

              All the more reason to get an attorney! An administrative agency is unlikely to tell someone, “Oh, BTW, you may have a discrimination claim.”

              1. justcourt*

                That is really not the way a human rights commission works, though.

                Going into the purpose of a human rights commission and the type of people who work there seems unlikely to make a difference at this point, so I will only repeat:

                1) I have actual experience with HRCs. I worked at one in one state and with several from other states
                2) the majority of complaints involved low wage jobs (because most jobs are low way jobs) and a significant number of those had no representation
                3) someone can get an attorney at any point

        2. MK*

          Eh, that kind of proves my point. The process you describe above might seem simple to you, but is very likely to be overwhelming to someone who is not accustomed to dealing with things like that (and depending on the level/quality of their education). The first step alone “submitting the complaint” is very easy to mess up, when you aren’t familiar with what is relevant, what is important to include and what is better not said, and stating your case in a clear manner is not a common skill. Many people, even those with university degrees, would either leave very relevant information out or harp on a fact that seems important to them but doesn’t actually affect the matter or write a too-long and difficult to read complaint etc. You keep mentioning “help of agency staff” and I would agree that if the agence is staffed by compentent people trained and willing to help and who have time to do so, one will probably be just fine without a lawyer, but unfortunately that is not a universal situation, and covid has made things worse. In this particular case, when the agency isn’t even answering the phones, I doubt the OP will get much help from them.

          1. justcourt*

            First, I am talking about a discrimination claim which falls under a different agency from UI. Unless I’m missing something, LW has only contacted UI, not his/her state’s human rights commission.

            And when I say staff help with the complaint, I mean they can listen to the complainant’s story, ask relevant questions, write the complaint, and serve the defendant. It’s a completely different process than UI and a traditional court system.

    2. WellRed*

      I think the bigger issue here is OP can’t get in touch with anyone. Our UI office is like that. I was overpaid about 3 weeks worth and am being careful not to touch it as I know they will come looking for it eventually.

      1. justcourt*

        LW mentioned not getting ahold of UI. LW didn’t mention contacting a human rights commission.

    3. Delta Delta*

      As a lawyer I’m going to take a different approach. While it’s true that there are actions that happen which don’t *require* a lawyer, there are lots of people who find the situation and the system too fraught to navigate on their own. Unemployment likely has its own system, deadlines, steps, and lingo – and a regular person who doesn’t deal with it day in and day out may feel overwhelmed by the system itself. Add that to the fact that they’ve lost a job and have no income – it’s layers of stress. Sometimes what someone needs is another person who can efficiently and effectively speak the language (so to speak) and get them through to the other side.

      I’m also going to ask Allison to modify her answer a touch. Not every lawyer will consult for free. Some will and some won’t. It’s always best to ask about fees up front.

      1. justcourt*

        That’s why I only mentioned a discrimination complaint. I’m not sure if you’re familiar with how discrimination complaints are handled by agencies, but the agency generally conducts its own investigation (no need to go through discovery) and handles defendant motions. The agency can’t offer legal advice, but the staff do most of the work that a plaintiff’s attorney would do.

      2. yep*

        Seconding the last part of this. For some lawyers, free consultation is a great business model. This is definitely not universally the case. My father is a lawyer in his 70s who has a great reputation in his area, and he’s often referring out clients and cases to other attorneys because he has more work than he needs. It doesn’t make financial sense for him to take time away from his busy caseload of paying clients to give out free advice. He bills for consultations as he would for anything else. This has occasionally led to anger from people who assumed there would be no charge but never actually confirmed that. It is absolutely worth discussing this point in advance.

  15. Grumpy Crustacean*

    Re: #3, my issue isn’t that I have nothing to report (though I don’t), but that I am getting increasingly angry over people sharing their perfectly normal holidays that flagrantly flouted public health guidelines, when their utter selfishness is a big part of the reason I’ve had to be locked down for nearly a year and am losing my mental health. I just want to say “I did NOTHING. Because there’s a PANDEMIC” very pointedly and loudly which isn’t a good idea.

    If it were just a case of having had a bad holiday myself, I’d be able to handle it in stride.

    1. OP3*

      Lol – same! I got locked down for christmas because people weren’t following the rules – but then they all just went home anyway! Seems very unfair but I try not to get caught up in that and focus on myself. I don’t know what people are dealing with after all. Hugs!

      1. Keymaster of Gozer*

        Here’s one thing I’ve learnt during this horrible time: if I get to the end of a day and I’ve not ended up back in the psychiatric ward it’s a victory for me. My achievement of say, getting dressed and finding my masks in the morning over the season is just as important as someone else spending the season getting hammered with their mates.

        Well, I’d add ‘getting to the end of the day without random cat attack’ to that but kitty is I think getting annoyed with the house being occupied 24/7. Cats, the ultimate coworkers…

        1. Chilipepper*

          Cats, the ultimate coworkers…
          OMG, now I am picturing all my coworkers as either cats or dogs. And somehow, that is comforting.
          Like, of course he is hanging around like that, he is a puppy dog or no wonder she does not talk much, she is a cat.”
          In case it is not clear, I am at work 8 hours a day with coworkers and the public.
          Even as I type, all the public is being re-framed in my head as dogs and cats. I am quite amused by this!

          1. Keymaster of Gozer*

            Hopefully your coworkers don’t stick their tails up yer nose and then loudly clean their bum right when you’re trying to have lunch!

            (Then go bonkers on catnip and tear round the place at Mach 5 before divebombing onto your lap. Not sure how you’d write a PIP for that….)

          2. Red Reader the Adulting Fairy*

            I am a cat-like standoffish introvert who prefers dogs. My husband is a dog-like goofy extrovert who prefers cats. It works for us. :)

    2. Person from the Resume*

      I had the best time off over the holidays. I imagine it must be like retirement. Nearly everyday was unscheduled, didn’t set my alarm, took advantage of nice daytime weather to ride my bike, chilled out and read. I got to the point where the top of my to do list had things that have been on it for years and were never urgent enough to rise to the top over the endlessly repetitive tasks of maintaining the house and myself (ugh cooking and cleaning). It was not Christmas-like, but so relaxing.

    3. not my usual name*

      Yes, this. I stayed in my city while many of my coworkers traveled against public health advice (although it wasn’t explicitly forbidden to travel in the U.S., just discouraged, and millions of people traveled anyway). I purposely logged into our team meeting 10 minutes late yesterday citing “internet issues” mainly because we usually spend the first 5-10 minutes chit chatting and not discussing real work. I’m not proud of that, but I couldn’t stand hearing about people traveling. I’m expecting other people to ask me about my holidays, but there probably won’t be a full discussion of the highlights with anyone outside my team.

  16. Mx*

    #1 Age difference is irrelevant in love. They wouldn’t be the first couple with a high age gap. One of the most in love couples I know is 26 years apart. Sure, there have been some gossips around them, but no more than for same sex couples.
    The problem here they work together, not the age. They are both adults over 18, it is all that matters.

    1. WS*

      I don’t think it’s irrelevant, but nor is it a stop sign. It’s one thing to take into account among others.

    2. MK*

      The age-gap couples who made it usually are the ones who took the challenges of their situation seriously, not the ones who spouted sentimental platitudes like “love conquers all”. It’s very much not irrelevant, like any other incompatibility, and if you want your relationship to succeed, you need to take it seriously and do the work.

      1. Whynot*

        My husband and I have an age gap of 14 years; we met when I was in my late 20s and he was in his early 40s, and are now in our late 40s/early 60s respectively.

        Age differences do matter, and matter differently at different points, because each person is at a different life stage. When we started out there were huge differences in terms of where we were in our careers, salaries, etc, as well as how we were thinking about things like taking risks for new opportunities, not to mention different levels of romantic/relationship experience – and I was in my late 20s, not 21 and just starting adulthood. After 2 years we split up but remained friends; I ended up pursuing grad school overseas. Six years later we got back together, and have been ever since. These days, there are still lifestage issues to deal with – among them, he’s nearing retirement and I’m nowhere near it. We’re happy, and I wouldn’t trade our relationship for anything, but age differences have had an impact along the way.

        All of which is to say: I fully agree with MK. Age difference is not irrelevant. It doesn’t mean that love can’t thrive across an age gap, but it’s important to go in clear-eyed about the potential challenges, and it’s important to realize where there are power differentials, especially when one party is a very young adult.

        1. Something Something Whomp Whomp*

          +1. Thank you for your thoughtfulness – see folks, you can be pro-age gap relationships without reducing issues to platitudes!

          As for the OP, I doubt that anyone would be focused on their age gap’s contribution to power differential issues if they were 36 and 51 respectively, or perhaps even 27 and 42. Heck, it might even be less relevant if they didn’t have a reporting relationship or even worked together.

        2. The Rural Juror*

          Not my situation, but the dynamic of two close friends of mine. They have a 15-yr age gap, but similarly they knew each other for years and the younger one was nearing 30 when they started dating. They entered the relationship cautiously and worked very hard to get to know each other as partners (including a few sessions of couples therapy) before getting married 3 years later. Their marriage is strong, but definitely has its challenges, with most of those challenges being directly or indirectly related to their ages.

          I agree with both you, Whynot, and Something Something Whomp Whomp, that where they were in their lives and how much hard work they put into their relationship is what has made them thrive. Adding the extra complication of working in the same environment doesn’t make things any easier.

      2. pancakes*

        I broadly agree that good relationships generally require a bit of work, but taking it seriously isn’t at all the same thing as taking any and all conversations with third parties about it seriously. Sometimes people turn to platitudes in conversations like those to signify a lack of interest in going into more detail. I’ve been in a couple long and happy relationships with significant age gaps, but I generally try to avoid discussing the subject with people who aren’t close friends because so many people are tedious about it.

        1. Something Something Whomp Whomp*

          Sometimes people turn to platitudes in conversations like those to signify a lack of interest in going into more detail.

          And then there are people who more or less think in platitudes and use them without quite realizing how they contribute to the conversation. Or who are accustomed to conversations where people just platitude at each other. I’m not sure it’s possible to have any sort of substantive conversation with either type, even if they’re open to it and are close friends, because they simply don’t have the tools.

        2. MK*

          It really doesn’t matter what you tell other people; it’s what you tell yourself that’s important. When I spoke of people spouting platitudes, I didn’t mean to me, because I honestly never questioned anyone’s choise of a much older/younger partner. “love conquers all” and “age is just a number” is unfortunately what a lot of people tell themselves, and it rarely ends up working out well.

      3. tiny cactus*

        I would also say that the age gap is most relevant when one of the parties is as young as the OP, because there is likely to be a serious imbalance of life/relationship experience and power. The gap between early twenties and mid-thirties is a lot more significant than, say, mid-thirties and early fifties.

        1. Alice's Rabbit*

          Very true. At 21, you’ve still got 4 years before your brain has finished adolescent development. Yes, legally you’re an adult, but the brain is not quite there yet, which is part of why people often change a lot in their early 20s. After 25, it still takes time to settle into your new cognitive normal.
          So the difference between someone in their early 20s and someone in their 30s is much, much larger than the same age gap would be even 10 years down the line.
          Add in the power differential at work, and I am seeing some large red flags.

    3. Batgirl*

      I think it’s irrelevant to some people and if that works for them, that’s wonderful. Not everyone feels that way though and we don’t know what this woman’s opinion is, much less if she’s in love. For me age is an important compatibility factor and when I was online dating in my early thirties, I took a very dim view of all the fifty somethings in my inbox who ignored my age preferences in favour of the Hugh Hefner formula (seriously, they were all double my age minus seven). Especially when they lectured me about ageism. Also, I don’t think you meant to imply this but 18 year olds are actually pretty vulnerable while they are new to adulthood and it’s seriously not ok for them to date people who are 20 years older.

      1. I Wrote This in the Bathroom*

        I was in my early 40s when I dated online, and ignored both the 60-somethings and the 20-somethings. One guy 25 years my senior listed his (extremely high) income and his (very well-paying) job title on his profile, and that irked me enough that I replied to him (I tried to warn him that it will attract people wanting to take advantage of him. he called my message self-aggrandizing and wished me good luck with my next victim. He also informed me that he gets many many dates with 40-year-old women; proving me right I suppose?) I did get lectured about ageism. I did once receive an offer of a free dinner at a nice restaurant (not an online date, someone I knew from a meetup group) if I agreed to pose as his girlfriend during his weekly dinner with his group of friends and to “not mention my age discrimination issues to them”, yes he said “age discrimination”, as if my body was an equal-opportunity job available to anyone who’d apply. Barf. I did not answer and ignored the man afterwards. The 20-somethings, shockingly, did not understand the word no very well either. Sorry for an inadvertent trip down memory lane!

        But this is different. This is not someone who saw a nice photo and a bunch of numbers that he liked on a dating app and said to himself “I need to have this shiny object”. These are two old friends and colleagues. While there are other factors that would lead me to advise against a relationship (she is still a manager at his workplace, different location or no!), this is not the same.

        1. Batgirl*

          “… as if my body was an equal-opportunity job” Yes! See also the men who demand a run down of reasons for rejection.
          I agree too, that this is very, very different precisely because there is no sign of lecturing or other patronising moves. We have two people with a respectful and friendly relationship. That rather makes me inclined to believe that the older person would be at least inclined to worry about age imbalances. It might not be a deal breaker but I doubt she’d breezily dismiss it as age doesn’t matter.

      2. UKDancer*

        Ditto on the men in their fifties emailing me as a thirtysomething. I was really not interested and they seemed quite annoyed about the fact. I did have one complaining about ageism when I said no thankyou. I don’t date people more than 5 years either side of my own age so to me age is an important factor.

        1. Batgirl*

          I don’t think they realize there are so many others in your inbox: exact same age, exact same lines. They are legion.

          1. UKDancer*

            Yes, I thought it was just me until I compared notes with a friend who was also online dating and she had exactly the same thing, an inundation of men in their 50s who wanted to date much younger and got annoyed when they were told no.

            1. I Wrote This in the Bathroom*

              (Offtopic, for which I apologize) Good news, this behavior has an expiration date. One of my former 60-something suitors found me in a Kik chat some years later and wanted to catch up, and I was understandably apprehensive. He said, “I’m 75. I am burned out on women and relationships at this point. They are too much work and I am tired. I just want to spend my time alone with my dog.” It was such a weight of my shoulders tbh, to realize that most of his age peers probably felt the same, and as such, were no longer going to be a problem.

              1. pancakes*

                That’s nice, but it’s just an anecdote about one person. It doesn’t establish that other hetero men around the same age share the same mindset. I don’t see why you’d think it does, or want to. Treating individual people as ambassadors for their generation, sexual orientation, etc. is unfair and inaccurate.

                1. I Wrote This in the Bathroom*

                  Numbers aside, I’m certain that for all of us, there comes an age (I’d guess in the late 70s or 80s) when we are FAR more invested in staying healthy and getting through our day in peace than we are in meeting new romantic partners young enough to be our children. Valar morgulis and all that.

              2. Batgirl*

                I wonder if this is the same guy I used to work with (similar age) who announced angrily that dogs were more loyal and obedient than wives. We didn’t ask him to explain further. I do think there is an expiration date on the hope that women will go for what the entitled and presumptive cohort are offering. But they keep the hope alive a long time.

      3. Mx*

        “For me age is an important compatibility factor” : And it is totally your right to prefer someone not older than you. It is certainly not ageism. It would be the equivalent of saying that someone wanting a partner of the opposite sex is homophobic.
        But this doesn’t invalidate the choice of other people who prefer a much older/younger partner. They have the right to be respected.
        It’s ok for 18 years old to date people 2o years older if it is what they want. I have done it (I was actually 19 but not a big difference) and it was a beautiful experience. The majority must be at 18 for a reason.

    4. LTL*

      “They are both adults over 18, it is all that matters.”

      No, it’s not. An age gap is a real thing and the line of reasoning I quoted here is very commonly used by predators. I would please, please encourage people to not promote it. A large age gap isn’t necessarily a dealbreaker but that’s different from saying it doesn’t exist and never matters. Like I mentioned above, “There are some very happy relationships with large age gaps” and “be very mindful of large age gaps in relationships” are two statements that can coexist.

    5. Yorick*

      It matters for the advice because this person may not be interested due to the large age gap. It’s something for OP to think about when he tries to figure out whether his work friend may be interested in dating.

  17. rudster*

    Uf, I have been wondering about the holiday wishes myself. I am a freelancer and almost all of my existing clients’ first contacts after the holiday have started out with “Hope you a great holiday!” and “Have a great/Best wishes for 2021!”, etc. Well, we had two powerful earthquakes right after Christmas and everybody here is on edge all the time, and to top it all off on New Year’s Eve my father collapsed and died unexpectedly. So far, 2021 is just shaping up to be more of the utter disaster that 2020 was! It seems disingenuous to just pretend like everything is fine, but obviously I don’t want to burden people with bad news (even if my long-term clients know me well enough that they would probably care) or make them feel bad for their holiday wishes when they could not have had any idea of my situation.

      1. rudster*

        Thank you, WS. He was 81, but was otherwise in reasonably good health so it was still quite a shock.

    1. WellRed*

      Happy New Year is a pretty standard greeting for me this week when reaching out on biz. I’m not making assumptions or trying to make anyone feel bad. I mean, would how are you feel any better? Just say thanks and change the subject. Better yet, take time off to grieve. I’m so sorry about your Dad. It’s shocking to lose a parent.

      1. WellRed*

        Oh and adding, my brother died in September unexpectedly. Even casual work contacts were very sympathetic and understanding. Please take care of yourself.

    2. Sleepless*

      I’m so sorry. I’ve had a number of losses over the years either around Christmas, or that have been magnified by Christmas. I genuinely don’t like Christmas for a number of reasons. Even pre-pandemic, I’ve found that I don’t even really have to hide that fact from people, because they are not listening anyway. If they ask brightly, “How was your Christmas??” and I give a half smile and say, “meh, glad it’s over” they will act like I said “It was great! I love Christmas!”

  18. Jenny*

    Look, LW1 is an adult, but you need to know that those of us who are older see statements like this as a red flag “Keep in mind I am not your typical 21-year-old. People tell me frequently that they think I am in my late twenties or early thirties because I present myself in a more formal / structured manner.”

    To be clear: the “but you are mature for your age” is something people often say to younger people (particularly teens, which LW1 is not) to justify exploitation. You may have heard something similar from a 16 year old dating a 28 year old.

    You are 21, you shouldn’t want to be anything other than what you are. And feeling like you need to present as older to justify your relationship is a red flag. Particularly because there’s also a power imbalance built into your relationship.

    Again LW1 is an adult, so there’s nothing illegal here. But I’m going to suggest the dynamic here may not be healthy if it needs to be justified with “I am mature for my age”. It’s fine to be 21! There’s nothing wrong with being 21!

    1. Kim D.*

      Could not agree more.
      LW #1, I say this in the kindest meant way possible. It takes the average human until 25 years old for your brain to mature completely. You, at 21 years old, are literally incapable of accurately gauging whether you are truly mature for your age; you probably lack experience and time to contextualize. Maybe you are! But, like Jenny says, there is also nothing wrong with being a 21-year old when that’s your age.

      1. Littorally*

        I would say that no one is really capable of judging how mature they are from the inside, regardless of age. It’s one of those things, like being well-spoken or attractive or charismatic, that really exists in the eye of the beholder.

      2. Mental Lentil*

        Oh, this! All anyone has to do is google “frontal lobe maturity” to read the research on this.

        I’ve known a lot of young people who claim to be mature at that age. What they meant was that they were intelligent. But intelligence is not the same thing as emotional maturity.

        And if an older person is interested in someone whose frontal lobes still are not fully mature, maybe they are not emotionally mature either. This has red flags all over it.

        1. UKDancer*

          This was me. I was intelligent, and didn’t get drunk or high and read a lot of books about philosophy. What I was not was emotionally mature and I wince in retrospect at some of the things I did in the interpersonal relationship sphere.

      3. anonymous 5*

        Given how frequently I hear people talk about how “mature” someone is for their age, I have started to wonder if people of xyz age are, in fact, generally more mature than what the particular age is typically given credit for. But either way, a self-assessment is probably not a particularly reliable gauge.

    2. Chilipepper*

      Hard agree. Focusing on a justification like that could be a sign of not being mature. Be yourself (which you are likely still figuring out, as are we all).

      When she asked for advice, I told my much younger friend to focus on the present moment, is she feeling happy, comfortable, safe right now and to keep going if she is, change things if not. In other words, stop thinking of other people’s judgement and focus on your personal experience. She says that helped her a lot. Maybe it is helpful to the OP.

      1. Batgirl*

        I wouldnt say OP is not mature. For me, the worrying thing is that they are focusing on the very human desire of impressing others and getting validation that you’re doing OK. That’s the whole reason behind why you should not date senior people!

    3. Georgina Fredrika*

      I think it’s also possible that LW is reading too deeply into what people say offhand (as we all do from time to time). Just wearing a different cut of clothes or having a different haircut can cause a lot of people to guess age absurdly wrong. I’ve told my roommate before that she seems way older/more mature than she is at times (23), and a lot of people would guess she’s in her late 20s, buutut there are other times where she is extremely her age. And there’s nothing wrong with being your age!

    4. Dust Bunny*

      It’s also entirely possible to be unevenly mature for one’s age. When I was 21 I was too mature to be into blackout drinking or bluffing my way through a job interview or a lot of other things that 21-year-olds are sometimes convinced they can handle, but I was not that mature about everything. And I wasn’t an extra decade and a half mature about anything.

      1. RagingADHD*

        Exactly. There is a huge difference among:
        a) being composed or having a formal comportment,
        b) generally avoiding stupid mistakes or substance issues, and
        c) having actual relationship skills and self-awareness.

        “Maturity” isn’t a single attribute. It’s a matrix of multiple life skills, understanding & judgment, and emotional development.

        Saying “I’m not like the average 21-year-old” is a wonderfully, perfectly 21-year-old thing to say. And that’s exactly as it should be.

        1. Something Something Whomp Whomp*

          I love how you laid out those differences. That part about being composed is important, because it’s the one part of “maturity” that you can easily pull off through affectation or a studied performance, rather than requiring life skills or life experience.

          1. Hello, I'd like to report my boss*

            This is exactly what I wanted to say but you put it perfectly.

            Signed, someone who was very good at appearing composed and avoiding stupid mistakes but had (has?) deficient relationship/interpersonal skills.

      2. Jenny*

        I mean I wasn’t getting blackout drunk at 21 either. I was intensely focused on school and my career. But that’s normal for a 21 year old, and part of why I am married to the person I was dating at 21 is that he also was intensely focused on school and we basically studied together. A guy who got mad because I couldn’t go on a date because I had to study for a quantum mechanics final was quickly dumped.

        1. Dust Bunny*

          The person I was dating at 21 and I were both committed to school but absolutely clueless about relationships (and he came from a completely dysfunctional family) so if we had married we would either be divorced now or I’d be in prison for strangling him with my bare hands because he made one too many “your momma” jokes.

      3. Jackalope*

        I really like the point about uneven maturity. I had some life experiences as a young child and a teen that matured me in ways that other people my age usually didn’t experience, so I could definitely give off the “mature for my age vibe”. In addition, as someone who was an only child for a long time, I was more used to being around adults than other kids and so have always been able to hit it off with people a generation older than me. But I definitely had other areas where I was either much less mature or just had plain less life experience. Which is normal – we can’t make it through all life experiences on speed mode, and some experiences are only legally available when you’re an adult, so at 21 you just won’t have had time for all of them. But I’m much more mature and experienced now than I was then, and my experiences are much more rounded than they were at the time.

    5. Ray Gillette*

      Agreed. Notable to me is his description of himself as “a 21-year-old male.” In my experience, young men who use “male” as a noun aren’t quite used to thinking of themselves as “real adults” yet. LW1 is still working at the same job he’s had since high school and is likely a college student. With the pandemic there’s a good chance he’s currently living with his parents. All of these are perfectly fine, normal things for a 21-year-old.

      LW1, take it from someone who was pursued (sometimes quite aggressively) by adults in their 30’s and 40’s when I was your age: the biggest sign of my maturity at the time was my ability to recognize that even though I was legally an adult, I was not ready for an adult relationship.

    6. Rusty Shackelford*

      To be clear: the “but you are mature for your age” is something people often say to younger people (particularly teens, which LW1 is not) to justify exploitation.

      Yep. Or, on the not-quite-so-dark side, they say it to mean “I know a lot of people your age who are complete idiots. You don’t seem to be one of them.” It doesn’t mean you’re mature as in “wow, you have a lot of life experience and are very wise.” It means “it’s nice to see there are 21 year olds who don’t act as if they’re in a drinking contest all the g d time.”

      1. Alice's Rabbit*

        Yes! Or, in the case of coworkers, it can mean “It’s nice that you’re reliable and professional at work, unlike most of the young goof-offs who apply.”
        It doesn’t mean you’re on the same emotional or life experience level as someone that much older than you. Just that you exceed their expectations for your age in at least one way.
        I was frequently mistaken for being well into my 20s when I was truly only 13 or 14. Why? Because my parents had taught me how to behave in a professional environment, including how to dress like a responsible adult. I was also taller than the average teenager. So I often got comments about how people thought I was much older than I was, I was so mature for my age, etc.
        That does not mean I was emotionally ready for anything resembling an adult relationship. Especially not with an older partner.

  19. Urt*

    We don’t even know whether the crush even if is romantically interested or will be crushed when they find out that their hiking buddy wants more.

      1. I Wrote This in the Bathroom*

        No kidding, poor woman thinks she is just hiking with a friend, and would be shocked to find out that she’s a Mrs. Robinson to a whole slew of commenters on a forum.

  20. alpacabear*

    LW #1 This is a sweet/hopeful story. I agree with Alison’s process for vetting the circumstances, especially different priorities due to differing stages of life. But as someone whose husband is 12 years younger than me, starting out as acquaintances, I can attest that it’s possible that these two folks could get together and be the real deal. Check work policy, ask for the date, be prepared to remain warm and respectful regardless of the outcome, and you’ve got nothing to lose. Good luck LW #1!

    1. t216*

      I don’t think it’s a sweet story at all. It’s great that it worked out for you but that’s the exception, not the rule. He should proceed with great caution, or not at all. OP saying that people think he’s more mature than his actual age is also a yellow flag. I had my life together and thought I was mature when I was 21 and now that I’m not, I can certainly say that I wasn’t as mature as I thought I was. You learn and change so much in your twenties! The gap in life experience between someone who is the age of a senior in college and someone who is a few years from being 40 years old is massive. There are also so many practical relationship considerations to think about with an age difference that big.

  21. Good Vibes Steve*

    LW3: I’ve used “I’ve had the kind of Christmas you could expect in 2020” as my boilerplate. It explains it all, and has the nice bonus of being a bit passive-aggressive to people who did not have a safe Christmas.
    I also haven’t seen my parents and siblings for over a year, as we live in different countries; and seeing people casually travel to other continents (“oh, but we’ll *quarantine*”) during the break has also left me feeling like crap.


  22. Dust Bunny*

    OP3: This just isn’t something about which you need to be honest, or at least factual. I spent my week between Christmas and New Years mostly cleaning the house, which was great in its own way but hardly the answer anyone wants. Nobody is going to be hurt here if you obfuscate, and the moral superiority of never lying is wasted on occasions like this. Just say you didn’t do much. Saying it wasn’t a great holiday might invite inquiries, but not doing much sounds boring and nobody wants to hear more about it.

  23. LGC*

    Okay, as someone who is your former manager’s age, LW1: what’s giving me major pause is when you said that you’re more mature than a typical 21 year old. I mean, I don’t doubt that you have your act together! But…I’ll be honest, this line has been uttered by quite a few young women who date older men with power over them (like their professors). It’s a strange sort of…naïveté? Hubris? A mixture?

    This isn’t the type of answer you were looking for, but yeah, I don’t think you should ask her out yet.

    Also, again, if she’s anything like me, she doesn’t have her act together, she’s just good at pretending like she does.

    1. CommanderBanana*

      I feel like having to say that is proof that it isn’t true. Intelligence is not a substitute for wisdom – I’m as smart now as I was 20 years ago, but I’m wiser, because I’ve learned more, and that only comes with time.

      Also? To all the 21 year olds out there, it is okay to not be mature beyond your years!

      1. Archaeopteryx*

        And while it’s perfectly possible to be on the mature end of 21 year olds, the gap between a mature and an immature 21-year-old is much narrower than the gap between a mature 21-year-old and almost any 36-year-old.

        1. Dust Bunny*

          THIS SO MUCH.

          You might be a mature 21-year-old but it’s highly unlikely you’re 15 extra years’ worth of mature.

    2. NotQuiteAnonForThis*

      Same….this line just throws a flag off in the corner where its barely in my vision, but its there. Its just not healthy.

      Its not a screaming siren (like the guy in Dazed and Confused played by Matthew McConaughey, the whole “I date high schoolers because they stay the same age no matter how old I get” vibe. Eww.), but its still there.

    3. LGC*

      And yes, I’m aware that LW1 is male and the manager is female, and it’s not quite the same thing. But it’s giving me similar vibes.

  24. Caroline Bowman*

    Re Christmas ”oh it was quite pleasant under the circumstances, we’ve been luckier than many” has been my go-to response to people I don’t know terribly well. Obviously if it’s been dreadful and tragic, adjust to ”it’s certainly been a tough one, but I know so many others are in a similar position, let’s hope 2021 is better!”.

    1. Chilipepper*

      I like this because it allows me to sort of throw snark at the people who are selfishly not following the things we have been asked to do. Not very mature of me but here we are. If they ask anything past that, I can say I safely stayed home with my sig other and spoke to my child on the phone, we all had enough food, still have jobs, we are lucky!

  25. animaniactoo*

    LW1 – Before you ask her on a date, ask whether she’d be interested in going on a date sometime. Your job is to make it clear that it’s not the entire reason you’ve stayed friendly all this time and that it’s more of an “exploring a possibility” thing as to whether she’d be open to it. It’s a lot easier to come back from that as a friendship than it is a straight up “asked out on a date and got turned down flat” with the resultant high emotions/awkwardness on both sides.

    LW4 – I am so sorry to say this, but please be aware that the overpayment might not have gone to you. Many many people had UI claims filed in their names with payments that went elsewhere. The scammers were quite busy. My sister (who never filed at all because she never lost nor was in danger of losing her job) has been a victim of this and is dealing with it now.

    1. SweetTooth*

      Ehh for LW1 I don’t think those are different enough sentiments. It’s pretty transparent that asking “theoretically, would you be interested in going on a date with me?” is a lead-up to “ok so will you go on a date with me?” It would come across as naive to behave otherwise.

  26. Hogsmeade AirBNB*

    LW1– If my math is right, this woman has known you since you were 17???

    Nope. Nope. No. Do not engage.

  27. Wondering*

    Removed. Please use the “report an ad” link above the comment box — I don’t want ad reports here, because I won’t always see them (and I need to). – Alison

    1. Wondering*

      Well it wasn’t about the ad itself but rather the quantity and general obtrusiveness of all of them. No offense but I’m not going to take the time to report the 10+ ads that take up my screen.

  28. SomebodyElse*


    I think some of the comments got sidetracked by the Diary/Journal/Calendar discussion… Whatever it was that your wife read, I do agree with advice given in the response.

    The first thing your wife needs to do is figure out for herself if there is any truth to the statement. Does she have coworkers that she can benchmark herself against? What clues has her manager given her about her perception of your wife?

    Either way, what was written was either an accurate assessment or it is an inaccurate perception. Regardless your wife needs to either fix the problem or fix the perception. I have no idea if this is case with your wife at work, but I’ve had employees and coworkers who think they are being super efficient, working really hard, and getting a lot done, but in reality, they are spinning their wheels, doing unnecessary/non value work, and generally just being a not great employee.

    I would advise that your wife really take a hard and honest look at herself before approaching the manager.

    1. Alice's Rabbit*

      Perception is definitely key. For example, #2’s wife might be excellent at her job, but the boss just happens to keep catching her at the wrong moment, when she is taking a short break between tasks, or grabbing something from her purse, or thinking about how to proceed on a task. All of those are perfectly normal things to do throughout the workday. But if that’s all the boss sees, it could erroneously lead to the conclusion that she’s goofing off, instead of just not looking busy.
      Optics are important.

  29. blink14*

    OP #4 – I’m so sorry to hear about your struggles! The most important thing is you got the surgery you needed. In addition to Alison’s advice in regards to the unemployment situation, talk to the hospital billing office where you had your surgery. Explain the situation and ask to set up a payment plan, most hospitals will do this. If they don’t agree or the bills are so much that a payment plan is unreachable for you, look into charities or aid societies that helps cover medical expenses. Googling your city and/or state is a great place to start. If your condition is well known, there may be a foundation or community that can help you as well. Your surgeon may be able to assist.

    Also be sure to really scrutinize the bills you’ve received, and if you still have health insurance, ask them to review the file to make absolutely sure there are no errors or incorrectly submitted billing codes. I once received a call from a collection agency about medical bills due to a doctor’s office that came to over $2,000. I had never once heard about this from my insurance or my doctor’s office, so I refused to give any information over the phone. Called my doctor, and turns out my insurance had taken so long to process the claims that they were void, and my doctor’s office (part of a hospital network) was covering the difference and continued to fight my insurance. Mistakes happen all the time in medical billing, it’s worth asking to have everything checked again.

  30. Jennifleurs*

    Op #1 says: ”Keep in mind I am not your typical 21-year-old. People tell me frequently that they think I am in my late twenties or early thirties because I present myself in a more formal / structured manner.”

    I hear: ”Nooo, I’m seven and a HALF!”

    OP if you need to protest that much about your perceived age, you do actually have maturity problems to work through.

    1. I Wrote This in the Bathroom*

      Yeah, in my mind, this is not very dissimilar from the “people tell me I am young at heart” that I used to get from men in their late 60s when I was in my early 40s. They were not necessarily lying. I guarantee most of them honestly believed they were 35-year-olds trapped in a 67-year-old’s body. Did not make them so.

      1. Sleepless*

        I mean…that’s what getting older is like. I’m 53, and inside my head I totally feel like I’m about 25. Until I spend time around actual 25 year olds and realize that no, I am in fact an entire generation older.

        1. Jackalope*

          I have that feeling too! When I’m around my friends from college it feels just like it used to, and we even do some of the same things together! (We had tame fun.) But for awhile I was volunteering with current college students, and while I loved it (they were a great group), I could feel the difference in our ages keenly.

    2. Anonosaurus*

      I kind of agree, but I also think that someone in LW#1’s position is going to clutch at whatever straw is out there to justify his feelings. So if a sales rep once thought he was 25, that’s going to feel like a check mark in the yes column – you look for ANY evidence to justify your crush when you’re in the grip!! Nobody ever thinks they’re a typical 21 year old.

      However I don’t think ‘being formal or structured’ (whatever that means) is anything to do with anything. Emotional maturity is not a function of intelligence, but of having experiences (and understanding them, including learning from mistakes). It’s just really difficult to accumulate emotional experience without life experience. Not your fault LW#1, just life.

      It’s quite possible there is sexual chemistry between you and this woman. This does not make it a good idea for anything to happen. Even if she is interested in you that way, she might be worried about what people at work would think (and with good reason), not want to be seen as a ‘cougar’ or cradlesnatcher – even if you don’t think of her that way, others will, and it not only sucks, it could risk her work reputation. She might not want to end up being your training wheels – she has emotions, too. If she is interested in marriage and children she is maybe more likely to want to date men closer to her age who might share that agenda rather than having a fling with someone as young as you.

      However, I have been on the other side of this, I had a crush on a younger man I used to work with – although he was older than you and I was not his boss, still no way I would have asked him out, because he was at work to work, not to fend off horny middle-aged women. If he had said something to me, though? I can’t put my hand on my heart and say I would have turned him down, but it’s better for both of us that this never happened, and I think the same might be true for you.

  31. iliketoknit*

    Re: LW#2 and diary v. journal etc – if the boss is at all into bullet journaling or such, they might use a notebook or calendar to keep track of work-related appointments, notes, thoughts, etc. which could include general notes about what they’ve observed in their employees that day – “X was lazy and pissed around, Y was really focused, Z came in late but stayed late” or whatever. Especially if they have a specific concern about consistent performance, I could see noting a particular employee’s performance on a regular basis, so that at some point in the future they could look back and figure out something like, “I noticed this problem X number of times in Y number of weeks.” (I fully admit I’m speculating, but thought I’d throw it out there.) If so, the weird thing is that it would be out and open on their desk, although it’s possible they were interrupted while using it and didn’t expect the LW’s wife to come in while they were gone?

    Also, FWIW, it’s not clear whether “lazy and pissed around” are the manager’s actual words, or the LW’s or LW’s wife’s paraphrase of what was written. Not a big point, but the language used might make the purpose of the document clearer.

    1. Ann O'Nemity*

      Yes, a bullet journal or daily planner was my thought as well. A place where someone keeps all their work notes, assuming that it will be confidential. I could totally see the boss writing herself a quick and angry note like “Jane was lazy and pissed around,” as a reminder to self to talk to Jane about productivity.

      In reading – snooping! – through the diary, Jane read the boss’s unvarnished thoughts. I’m sure Jane has some Feelings about this, but I’d hesitate before putting too much stock in it. It’s entirely possible that the boss jotted down this in a moment of anger, not intending it to be a sweeping assessment of Jane’s performance. Still, Jane can ask for feedback, and Alison offered some good advice to do that.

    2. Catherine*

      Yes, this! I use my bullet journal for literally everything in my life and it is always with me, open, on my desk at home AND in the office. Although I write anything remotely personal or sensitive in a different language using various alternate alphabets etc (people who can read Theban or Elian AND also the actual language my notes are in are rare here) to prevent just this kind of mishap.

  32. S*

    OP2 – regarding the diary, people use diaries/journals as a way of emotional regulation/venting. So while her boss’ perception of her may be true, it could be on just one day where she was really aggravated by your wife’s behaviour and had to vent her frustrations

  33. Observer*

    #2 – Why did your wife read the diary? I think that the answer to that will affect what her next steps should be.

  34. blink14*

    OP #1 – My suggestion is to not push the situation any further. Much like when you are in school with the same people day after day, sometimes a work situation creates an all encompassing feeling where it starts to feel like a huge part of your world or all of it. But, when you leave that world, like leaving high school or college, not seeing people on the day to day defines your real relationship with them. It’s highly likely that if you were to leave this job, you wouldn’t see or maybe even speak to your co-workers again. It’s natural as you move on to something else. I worked at the same summer camp for years, and while I still retain two close friendships from that time, even those relationships have evolved over time as our lives changed and just naturally took their own paths. There were others who felt like the best friends in the world in the summers we worked together, but we haven’t talked in years. Nothing bad happened, that’s just the way it happens. I know retail an create similar environments.

    It sounds like you and this woman are good friends, and you’ve known her since you were 19 and she was in her early 30s. Her and I are a similar age – and I can tell you that from my perspective, most women in their 30s being friends with a very young co-worker will see it as a friendship, or even feel like a mentor or an older sister to that person. There’s a much smaller chance that she has romantic intentions towards you. It’s possible, but not highly likely.

    You say that many people feel like you are older than your real age – does she actually know how old you are? If she doesn’t, that could spin the situation into a different light.

    1. Jennifer*

      Not to mention, a lot of us are just starved for affection now because of the pandemic. It’s not surprising people would look to people in their bubble for romantic companionship too.

  35. Sleepy*

    LW1: since you worked together, do you have any mutual friends you could pass this by?

    My sister met her husband at work. They each independently talked to mutual friends about their crush on the other, and the friends confirmed to them that both were interested before either of them made a move. It sounds high school-ish, but it avoided some of the awkwardness that could have resulted if one had asked the other out based on misread signals. (They were in different departments at a mid sized company.)

  36. I Wrote This in the Bathroom*

    LW2: I cannot wrap my mind around the fact that your wife’s manager 1) kept a personal diary/journal at work, on paper in writing instead of in digital form and under password protection, 2) left it open on their desk, 3) knowing that their subordinates would be coming to their desk to drop off email? Regardless of whether the manager’s assessment of your wife’s work is accurate, this is such bizarre behavior to me that I don’t even know what to advise.

    I am 10000% certain that my managers keep notes on how they evaluate my performance. But they don’t leave them open for me to find. I have no idea where those notes are, and I want to keep it that way.

    1. SomebodyElse*

      Eh… I don’t think it’s that bizarre.

      People get distracted… people get interrupted… urgent “hey can you come here for just a second” which turns out to be longer than expected happens… “Oh crap that second cup of coffee was a bad idea and I have 2 minutes before my next call” situations arise.

      Especially if you don’t usually get people coming into your office, I don’t. I get about 4 pieces of mail delivered to my office at work a year so that’s not a very common occurrence for a lot of people.

    2. Jennifer*

      +1 I’m almost wondering if she wanted her to see it. If I kept a journal at work where I talked crap about my coworkers, I’d make sure that was put away before I went anywhere. That takes 2 seconds.

      1. I Wrote This in the Bathroom*

        And in my line of work, where we are likely to have PHI on our screens or our desks, we have annual training to remind us that none of that should be out in the open when we are away from our desks. Lock our computers and put away all the papers. That is a job requirement. We can get in trouble for failing to do those things.

        1. Jennifer*

          Exactly. Even if I was called away on an urgent matter, I always took two seconds to lock my computer. The only time I could imagine not doing this would be an emergency situation, like the building being on fire, which we know didn’t happen.

  37. No Tribble At All*

    #1: Based on the Standard Creepiness Formula (half your age plus seven), a thirty-six year old can date as young as a twenty-five year old. A 36 yr old should not date a 21 yr old. You’ve worked for her since you were 18 (just barely not a child) and she was 33 (a normal grownup).

    Don’t do it, OP.

    1. Littorally*

      And the standard creepiness formula gives a pretty low threshold. I’m about the same age as the boss, and I would not personally consider dating anyone younger than their late 20s.

    2. LPUK*

      Yeah,the standard creepiness formula only works for a relatively tight set of numbers – late twenties, thirties – and rapidly gets more creepy outside those dates. Also as it’s often expressed in a gendered way, with the male being the old partner, it means that as a late middle aged woman, I should expect to get getting attention from centenarians – no thanks!

  38. employment lawyah*

    1. I have a crush on an older coworker, and we’re hanging out outside of work
    Well, the helpful thing here is that the normal unfortunate dynamics are absent: The woman is older and more powerful. That makes the task a bit easier.

    If you want to take the risk, you can ask once. Again, I repeat, ONCE. In a 100% non-creepy, straightforward way.

    The dilemma is that your first-and-only ask needs to be overt enough to be clear (you can’t repeat it!) and also needs to be non-creepy (not too much pressure!) The solution is usually to be more formal, rather than less formal. This is basically why formality exists. I am a big fan of including the word “date” because this has a specific meaning which conveys what you want.

    Consider something like “I like you and would like to spend more time with you. Would you like to go out on a date with me on Saturday night?” This is both 100% clear and 100% non-creepy.

    And also, do not raise this during work hours.

    Prepare your “acceptance of no” in advance!! If she says no, you shouldn’t blush, fumble, or make things worse. You should have a pre-memorized “No problem! I won’t bring it up again, and I won’t let this affect our working relationship.” Then, prepare for HER to limit the out of work stuff (such is life), move on, and never–NEVER–raise it again.

    Also, FYI, if she has reason think you’re way older than you are, that is not necessarily a great foundation for a relationship.
    2. My wife read her manager’s negative thoughts about her
    Well, are they RIGHT?

    If they’re right: Your wife should change her work.
    If they’re wrong: Your wife should take steps to change the manager’s mind.

    3. What do you say when you had a horrible Christmas break?
    “Nothing special! Hey, do you think those reports should be in red or blue?”
    if pushed,
    “I’m too busy to think about Xmas now that I’m back at work.”

    4. Unemployment says they overpaid me and wants repayment — but I can’t reach them
    Yes, I agree w/ lawyer or state rep.
    If you can’t get in touch w/ them, you need to document it.

    1. F as in Frank*

      For 1: if you decide to ask don’t do it in the middle of a night hike. Consider her perception of safety and pick a time and location where she has an easy out.

    2. tues_*

      Re LW1:
      Just because the woman is older and in a position of power doesn’t automatically preclude her from potentially being a creep. Women can abuse positions of power as well. A 15 year age gap between someone who is nearing middle age and someone who was a teenager two years ago is a red flag no matter the genders of the parties involved. The same red flags should apply than if OP was a 21 year old woman and the person in question was a 36 year old man.

  39. mdv*

    LW4: I work for a state university that had to furlough us for a few weeks in the summer. Even with all the work our HR did to make sure our unemployment claims were “easy”, there was a problem with the upload, and I had to make some calls. Each time I called, I actually had to sit on the phone hitting redial something like 75 times (almost 90 minutes) before I got through to the tier 1 call folks. That person hung up on me, so I had to call back another 62 times to get through again, and then a 2-hour callback time from the tier 2 folks. It was incredibly frustrating, but I also don’t think calling my legislators would have helped.

    All that to say … could there be a volume problem in the unemployment call centers in your state?

    1. SomebodyElse*

      I think WI UI call connection rate was a whopping 1% at one point. Not sure if it’s any better right now, it seems to be a quagmire for anyone unfortunate enough to have to work with them.

    2. Boopnash*

      In my state Unemployment is completely overwhelmed. They hired hundreds of people at the beginning of the crisis and it’s still overwhelmed.

      Even if a state legislator office can’t speed things up at this point in the crisis they can or should track and be able to be an intermediary for communication with unemployment and help navigate complex issues.

  40. Office Goblin*

    LW #4

    I know this may not end up being helpful, but I’d like to recommend you calling up your hospital and requesting information on how to ask for a charity write-off on your bills. I did this when I had my own life-saving surgery (and no insurance to cover it) and all of my bills were waived. You may have to contact individuals separately (the surgeon, the anesthesiologist, etc) but the hospital may be willing to do it for you, or at least advise you on how to approach it. You do not need to say why– the request itself tells them enough. Good luck with this, and I hope you get a good resolution!

  41. Anon for Now*

    LW #3. I have no advice, but I just wanted to share that I’m in the same situation. I had to cancel my trip back to England at the last minute. I had not seen my family for almost almost 18 months and that trip was one of the few things that gave me hope through all the insane stuff that has been this year. It’s likely that I won’t see them for another year. It sucks so much. And I’m so sorry that you are experiencing the same sort of thing. I know when people have asked me, I’ve always said, that I’m relieved that 2020 is over and I’m hoping 2021 is better. I mean what else is there to say? Especially when you know the person asking ignores public health advice.

  42. Jennifer*

    #1 Alison is right – you are very young and that is a significant age difference. If you were 30 and she was 45 it wouldn’t bother me as much. The age difference plus the fact that she’s a manager at the company and the late night hikes are setting off alarm bells for me. I’m just trying to think of this the same way I would if she were male. Even though you aren’t in her direct chain of command, she is in a position of power at the company. Definitely take some time to really think this over before you ask her out.

  43. KimW*

    Also recommending a lawyer for LW#4. I had some ridiculous issue with a medical billing several years back. It was going to cost me over $5000 simply because the doctor sent the bill to my insurance past the time window (more than six months after the procedure) and my insurance wouldn’t pay anymore so the doctor was billing me directly and wouldn’t budge. I literally googled for lawyers and contacted the first one I found by email. I explained the issue and the lawyer got back to me immediately and he said he was just so mad on my behalf he would handle it for free. All he did was write a scary letter on his letterhead and it was resolved within days. I know people like to make fun of lawyers but that guy was awesome! I hope you have the same good luck.

  44. JohannaCabal*

    #4 If the unemployment overpayment stands and you are unable to pay, talk to the IRS’ Bureau of Fiscal Service if you are due a refund. While your state unemployment can intercept federal and state tax refunds, it helps if you can contact BFS ahead of time.

  45. HugsAreNotTolerated*

    OP 1: I think you know the answer to your question and the answer is ‘Don’t.’
    What have your friends & family said about this? Was it pretty much a solid ‘No’?
    Did you write to Alison hoping for a different answer?
    If you’re playing the old “If Mom says no, ask Dad” game here with advice then it’s clear that you don’t have the maturity that you think you do and definitely don’t have the level of life experience needed to have a relationship with someone 15 years older than you.

  46. Leeloo*

    LW1 – I’ve been with my husband for 10 years, married for 7. We met at work and he is 14 years my senior. It can definitely work but it’s also a big, big risk. If it didn’t work out, one of us would have had to leave our job (we did not report to one another but it would have been a no go) and it would have ruined the friendship we had prior to dating.
    Age gaps seem to matter less as you both get older but you are barely a legal adult and she is nearing middle-age, not to mention you have no idea if she’s into you – I’d let it go. Also, age gaps can be hard! I love my husband but we had to have some difficult conversations when we got serious: how many kids would we have (spoiler: we have 2, wanted more but will not because my husband is nearing 50 and doesn’t want to be an “old dad”), life expectancy, and even cultural things because we grew up in different decades!
    I’m so glad that everything worked for us because we have an amazing life together (also the age gap at 30s/40s, people don’t even register it anymore) but I think we are the exception and not the rule.

    Also, sorry. Most people that say “I’m so mature for my age” or “I’m an old soul” aren’t nearly as mature as they think they are. :/

    1. Jennifer*

      I considered myself a bit of an old soul when I was younger just because I enjoyed older movies and books and didn’t have the same interests as a lot of people my age. But then I realized I wasn’t really all that more mature emotionally, I just had different interests and was more introverted than most people I knew back then.

  47. Keymaster of Gozer*

    LW1: I’m not going to say anything about the age gap or what have you because that’s been covered above.

    What I will caution though is that a global emergency is a time when people might not be at their best for making a big decision like ‘should I date this person who asked me?’. I don’t know if she’s under a ton of stress over this pandemic (some of us have been operating at crisis management levels for too long) and really relies on your friendly night hikes and chats for some sort of normalcy. So if you’d asked me directly about whether you should ask her out I’d read you Alison’s answer but also add a bit about maybe waiting till this unprecedented catastrophic situation has become more managed and less bad.

    Then you’re more likely to get a clear headed question and answer.

    (Note: I’m autistic married to an autistic man so my sense of what’s normal human interaction can be a bit off the mark. Another reason I work in IT and not HR)

  48. Ben Marcus Consulting*

    LW2: It could be that the manager is tracking performance issues via a calendar in order to show a timeline of events, but if that were the case I would have expected the manager and wife would have already had a conversation about this.

    It could be far more innocent though. I keep a diary (digital one) for work that I use to write down conversations before I have them. It helps me to see what I’m feeling and want to say to see if I’m being ridiculous. It could be that the manager is feeling that something is off with the wife, but cannot quite put their finger on it.

    I actually keep a separate diary for work, too. I use this to draft out ideas I have for strategy and keep a daily overview of what I’ve done (in case I need to recreate something or backup a timeline).

  49. boop the first*

    1. Yeah. Age gaps between two middle-aged or older folk is a bit different from an age gap with someone who was so recently a child. The risk of ex-manager seeing this as a life mentorship is just too damn high.

  50. whatchamacallit*

    LW #4 ugh that sucks. When I was briefly on unemployment and my payments weren’t getting deposited (I must have put in my account number wrong, and they would only verify the routing number over the phone, which was super frustrating because I wanted to just correct it if I typed it in wrong) I went down in person to the unemployment office to finally just talk with someone in person. This was pre-pandemic so it’s not ideal anymore but if you there if they have limited capacity for people to visit in a socially distant way it’s worth a shot.

  51. I'm just here for the cats*

    I’m Kinda wondering if the “Diary” is like a calendar but maybe the boss is tracking activities because she thinks Jane is lacking. Like Jane was 15 minutes late to the meeting. Jane was joking around and didn’t finish X. Things like that. If it’s actually a diary as in a journal with personal thoughts it is extremely weird to have that open at work, unless the point was for Jane to read it because boss is passive-aggressive.

  52. Handful of Bees*

    LW1: I skimmed through the comments and didn’t notice anyone talking about this but – we’re in the middle of a pandemic. Right now is /not/ a good time to ask someone to dinner. Eating out is one major way the ‘rona is spreading. Why has this not come up? I’m seriously concerned that treating even situations like this as ‘business as usual’ is extremely dangerous.

    1. Jennifer*

      I think that was just an example of how to phrase the question, if he chooses to ask it. But I have heard of people having dates in the park and bringing their own food and social distancing. Having dinner together doesn’t necessarily mean going to a restaurant and eating inside.

  53. lazy intellectual*

    Uhh I’m in my late twenties and would consider dating a 21yo guy to be way too young. Yikes.

    1. Alayna*

      Same. I think when you get older the age window widens (I.e. a 31 year old and a 40 year old) but I’ve changed so much throughout my 20s that dating someone more than 3 years younger/older would be a bad fit right now. It’s just a time of such rapid change and so many “how does this work” type experiences.

    2. Jennifer*

      I could see myself having a more casual, just for fun relationship with someone younger. It could never get serious though.

  54. Tidewater 4-1009*

    LW4, it doesn’t sound right to me that unemployment is asking you to pay more than they gave you.
    Did you receive a text or email telling you this? If so it may be a scam.
    When you get in touch with them by calling their listed number or going in person, go over all the details and make sure there’s no mistake.
    Good luck!

    1. Rayray*

      Unfortunately, it is a thing that state UI offices will ask recipients to pay back DOUBLE what they received if the state determines they overpaid, whether it was actually fraudulent or a case like this one where the employer is giving a different story. It’s happening in my state to people who didn’t realize they didn’t qualify for UI but got it anyway.

  55. Eclecticism is a Virtue*

    OP #1, a few things. First, in the retail world, it’s not uncommon to be transferred. In fact, the other person being transferred as part of a promotion opened up this entire conversation! What happens if she is transferred back, or you are transferred to her location? A better timeline, as hard as it may be to wait, is wait until one of you does not work for the company. Second, and this is not guaranteed but something to be aware of, there is a very good chance that even bringing this up is something you can never take back. Meaning, it will likely change the relationship no matter her answer. While the relationship may not sour, it could be different from how it is now. Is that something you are comfortable with? Finally, as Alison brought up, the other person is in a different place in life. How she approaches a friendship like this is very possibly different from how you approach it. In other words, are you sure of her interest, and it’s not strictly platonic? She may very well be interested in “more than friends”! But weigh what you know first.

    OP #3, I don’t know about in the UK, but in the US, “I’m fine” or “It was fine” is a generally recognized shorthand for “I don’t want to talk about it.” That’s it! Just say it was fine and ask about their break.

  56. Aggretsuko*

    I feel like a hypocrite on this one because the person I am interested in is….uh, younger, albeit not 21 younger (thank god), but I also hate age differences.

    21 is…skating things. It sounds like OP and she work for the same company and he’s out of her chain of command and he is legal so TECHNICALLY it could happen, but….is it it a good idea, I dunno. Once in a while that sort of thing works out, but it’s more likely than not. If he was 25, maybe.

    What I will point out is that she’s 36 and most women want children and she doesn’t have that much time left to waste if she does. (I hate having to say this since I am not someone who wants any, but most do, so.) Is OP willing to become a dad by say, age 22-23 if he gets involved with her and it goes well? Does he have any more oats to sow or anything like that?

    1. Yorick*

      This post makes a lot of assumptions, but it is true that a 36 year old and a 21 year old may have wildly different short- and long-term life goals and that can make them highly incompatible.

    2. Alice's Rabbit*

      You make a valid point. Even if she doesn’t necessarily want kids, most 36-year-olds aren’t looking for the same thing in a relationship as most 21-year-olds. LW probably isn’t ready to settle down and deal with long-term commitments like retirement plans and homeownership. Just because that’s not the stage of life he’s in. And that’s okay!
      But she is, and she needs a partner who is in a similar stage of life. She doesn’t have time to waste on a relationship that likely won’t work.

    3. pancakes*

      This is a very paternalistic mindset. There’s nothing in the letter to suggest that the manager is unaware of or unable to communicate what she wants in a relationship.

  57. nonprofit writer*

    LW#5, did you work for Bill Gates personally or for the Gates Foundation? (I’m extrapolating this from the “made-up” name you used). If the foundation, it’s not really name-dropping in my opinion and it would be silly not to mention it. Tons of people do work for the Gates Foundation! (I don’t say this to diminish your accomplishment–just to emphasize that their reach is huge. I’ve never worked directly for them but I’ve worked on several Gates-funded projects.) If the man himself–well, I’d ask someone in his office.

    1. LW#5*

      LW#5 here! The short answer is I did both! I feel very comfortable talking about the foundation work. In fact I can scarcely avoid it because it was the bulk of my job! However, yes, I also did work directly for him/a separate entity that represents his priorities apart from the foundation. Thank you very much for your recommendation here!

  58. Foxgloves*

    OP3, I’m in the UK too, and also had a horrible Christmas break- not just with the last minute change to restrictions, but with an appalling non-covid related tragedy in the family on NYE. I’ve been going with “It was very different than expected, but it’s always good to have a bit of a break from work. How was yours?” because if I say anything else I will cry. People aren’t pushing for more details as lots of people had breaks that were pretty rubbish this year- hopefully something along those lines works for you too.

  59. Alanna*

    LW1 – I can’t tell you how many men in their 20s have told me they’re “mature for their age”, and from my POV 0% of those men have been correct in their self-analysis. I say this as someone with a younger boyfriend who I adore (he’s 26, I’m 30)!

    I really, really don’t think you have a shot here. Honestly, I wouldn’t say anything to her unless she’s giving you VERY clear signals, and if she were you wouldn’t have written in. If you really feel like you have to say something, I would add onto Alison’s script something like, “I enjoy spending time with you. Could I take you to dinner this Saturday, not as coworkers? I understand our age gap may be a barrier here, and if it is I totally understand. Whatever your answer is, I hope we can continue our friendship and hikes without too much awkwardness”

  60. Caradom*

    Do you know the brain doesn’t finish developing until the age of 25? It also develops in a way that the regions responsible for cognitive control of behaviour develops last. I wouldn’t blink at 15 years if you were closer to 30 but you’re on completely different trajectories. Does she want children? If yes she is close to hitting a serious time limit whereas you are just starting out. It might seem odd to do this at the start but I would seriously recommend talking to each other about your goals and what you want out of life before you start dating.

  61. dan*

    If the OP is often dropping mail or work documents on their boss’s desk, perhaps she was meant to “accidentally” read it. That would be extremely passive-aggressive, but perhaps the manager has a problem with uncomfortable conversations.

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