updates: best friend is dating my employee, coworker tries to scare me, and more

by Alison Green on December 3, 2024

It’s “where are you now?” month at Ask a Manager, and all December I’m running updates from people who had their letters here answered in the past. Here are four updates from past letter-writers.

There will be more posts than usual this week, so keep checking back throughout the day.

1. My best friend is dating my employee

Your advice was to talk to the employee, because a bit of atypically personal interaction was warranted given how much the employee had to lose. So I did. I reiterated that I didn’t expect my friend to tell me anything so she could talk freely to him, and that while I’ve been his friend through numerous breakups and he’s never turned into a weird stalker/aggressive guy, if he did in this case I’d throw him out the same as anyone else. She said pretty much what he did, that she assumed none of that was going to be a problem, but that it was still good to hear it from me.

I also had a talk with our one middle manager-type employee, saying I was aware there might be an appearance of favoritism and I was guarding against that, but an extra set of eyes looking out for the same problem was welcome. She never mentioned it again, so I don’t think anyone came to her with concerns.

Some commentators wondered about banning these types of relationships, but that’s just not feasible in a small town nor in a bar environment, and certainly not in both. Another wondered about sexism in your response, but I thought that was nonsense.

Long story short (too late), we did go on one trip together and while it wasn’t 100% awkward free, it was short and fun and not an issue. And the main issue became moot when she quit (for good reasons: she was working for me as a second job to clear some debt, and once her finances improved she wanted more free time, which I totally respect). She and my friend are still dating, quite seriously, and we’ve gone on a couple short trips together that haven’t had any awkwardness.

She did hint a few months later about asking to rejoin our team a bit, and I demurred. I had several reasons, but one was that I didn’t want to reopen the issue. I worried about whether that was fair to her or not, but ultimately there were other factors at play (we didn’t really need another staff member, mostly). She and I are becoming friends, despite starting with a different relationship, and things are good.

I’m really glad I wrote in and you answered. It took an issue that hadn’t been a problem but that I thought might become one, and made it a total non-issue. Thanks for the good advice.

2. My boss is upset that I quit without more notice because I’m vital to the business

I did not realize just how toxic working for Amanda was until I started this new job. As some readers speculated, my letter was just the surface of the dysfunction. This was my first long term job in the professional world and I now realize how many red flags I ignored. This whole process has been like bad relationship/break-up.

Amanda reached out to me a few times after I left with questions. I answered at first but after a rude reply from her, I blocked her number. She had to hire two positions to replace me and, from what I have heard, she has had a hard time keeping the positions filled. I feel bad for leaving her in that situation but I also understand that she is one who created that work environment and it is no longer my responsibility.

My new job is amazing. It’s a night and day difference. I start at 9 am and I am done at 5 pm most days. I am not expected to be constantly accessible by phone. Most importantly, I no longer feel like I am drowning at work. I have PTO and a healthy work-life balance is highly encouraged.

And in the happiest news, my fiance (who encouraged me to leave) and I are just a few weeks from the wedding! I am taking almost two weeks off for the wedding/honeymoon and, hopefully, for the first time I won’t spend my time off checking in on and worrying about the office.

3. My coworker thinks it’s funny to try to scare me

I wanted to write in and give an update about the coworker who enjoyed scaring me. It feels like such a scandalous update compared to how bland my problem was but here goes.

So I did get him to stop startling me, at least on purpose. I will say I probably wasn’t as assertive as I could’ve been, looking back at it all these years later. But I asked him to stop and he stopped. I’ll still jump at innocent coworkers’ friendly hellos, but at the very least I’m just startled and not both startled and pissed. I remember some comments not understanding the difference between being startled on accident vs being startled on purpose and to that I say it’s the same thing as being tripped on accident vs being tripped on purpose. Both irritating, but one is usually followed by apologies and laughs and the other is rude.

But in the end, during Covid work-from-home, he was fired for asking another colleague for topless photos.

4. Is it unprofessional to ask to change desks because you don’t like someone?

I planned not to say anything until management told me who my new mentor would be, but it turns out I didn’t need to say anything. Today they pulled me aside and told me they’d picked a new mentor, and asked if I’d like to move my cubicle to be across the aisle from him, so I said yes. Thank you for your advice, I’m glad I let the situation work itself out.

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{ 73 comments }

{ 73 comments… read them below or add one }

  1. Potato Potato*

    Raise your hand if you’re surprised that the guy who enjoys scaring young women would get fired for being inappropriate in a different way

    *keeps hand down*

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    2. Potato Potato*

      Also, for the record, I believe the OP when she says he’s good at acting nice towards people. My experience is that folks like that reserve their not-niceness for people who they believe they can mistreat without consequences.

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      1. SHEILA, the co-host*

        Yep! The not-niceness comes out in one-on-one situations, and because of the establishment of the “nice” persona, many others are disinclined to believe anything that challenges that perception. “I can’t believe Fergus would say that to you, he’s so nice!” etc., etc.

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        1. Slow Gin Lizz*

          Yeah, that seems to be lesson one in that horrifying class, Abuser Training 101. And it’s why I now have a hard time trusting “nice” people.

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        2. Wendy Darling*

          I used to work with a guy who was constantly pushing boundaries but never quite to the level that you could, say, report it to HR without seeming like an oversensitive lunatic.

          At first I just thought he was a socially inept git but then I noticed that somehow he managed to never ever take it too far — he did just enough to make you mildly uncomfortable but not enough for you to complain to someone in authority.

          Which meant he knew exactly where that boundary was and was choosing to stay on the good side of it. If he didn’t know he would screw up and go too far occasionally, and he didn’t.

          His social skills were excellent, he was just using them for evil.

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          1. Archi-detect*

            That reminds me of something that was said on the sexual harrasment episode of Last Week tonight, if I recall: some people are always asking where the libe is exactly so they can get right up to it; if the line is an 8 second hug they will count to 7

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          2. Rob aka Mediancat*

            We have a rule banning stuff like that on a discussion board I’m on: We call it brinking, and repeatedly brinking is a violation in itself.

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        3. Lenora Rose*

          Also the reason I hate people asking if they’re just “socially awkward” (or have a diagnosis.) If they don’t say the inappropriate things to or in front of the boss, they’re not awkward, they’re targeting.

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        4. StarTrek Nutcase*

          IME the “nice” persona is also used by lazy or incompetent workers. I can’t count the times a coworker or direct report used this persona to avoid repercussions or try to obtain extras. And of course workers who didn’t directly work with them were anxious to point out “but she’s so nice” – like “nice” is sufficient substitute for poor work. If I had a choice, I’d take a grump who does reliable any day. I dare say I’d even take a PITA who does reliable work. I learned over the years I neither have to like or be liked by coworkers and prefer we all just do our friggin job.

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        1. MigraineMonth*

          Zero surprise here. $200 on the target of his solicitation being another young woman (likely new to the company and in a lower position in the hierarchy) who he’d been very kind to.

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      3. Ally McBeal*

        I mean, he wasn’t fired for asking c-level execs for racy photos! I read a lot of advice blogs and even venture into the cesspit of Reddit advice subs, and it’s always interesting to see people writing in about their partner’s/friend’s “uncontrollable” issues and then respond to “well, are they able to keep a job?” with “oh, hmm, I guess they CAN control their behavior, they just don’t control themselves around ME, I see now that I’m in a bad situation.” Way too many people have to have this pointed out to them.

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    3. Echo*

      No hands raised here either. There’s a pretty high Venn diagram overlap between “people who cross boundaries in seemingly small and benign ways” and “people who cross boundaries, period”.

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    4. Leslie Santiago*

      literally came here to say this. very unsurprised that this guy was not as nice as he was made out to be.

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    5. HiddenT*

      Very much a “where there’s smoke, there’s fire” situation. If it was all innocent fun, he wouldn’t have only been targeting two young women.

      I have heard of people whose startle response is to start throwing punches because of past trauma, may he be so lucky as to encounter one someday.

      Reply ↓
  2. Resentful Oreos*

    LW 3 – I’m glad your jerky coworker stopped when you said to stop. I hate when people try to trigger my startle reflex on purpose. But wow, that was sure a coda. Yikes. Asking for racy photos from a coworker?

    Between this guy and Ailurophobe Joan, we have a run of updates on coworkers who never mentally or emotionally left middle school. You’d think most people would know by now that you don’t ask a coworker for those kind of photos! Glad to hear he was fired.

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    1. Corporate Lawyer*

      Right?? I was like, oh, I’m glad things worked out okay for the LW … WAIT, WHAT?!?!

      However, after my initial reaction, I find the final sentence not at all surprising.

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    7. KTbrd*

      Yes! I saw I was nearing the end and thought “Really not sure what’s so scandalous,” and then…boom! What a (n unfortunately not that surprising) twist.

      Reply ↓
    8. Zeus*

      I had forgotten they had said it was scandalous by that point – excellent use of timing in that letter, bravo to the LW!

      Reply ↓
  4. SHEILA, the co-host*

    LW 1 – Honestly I’m glad to hear the employee moved on and that you haven’t brought her back on board. That’s the safest route for everyone. If she does need a second job again, offer her a good reference, and possibly an in with another team, but I wouldn’t bring her back on to your team.

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        1. Jackalope*

          I understood the “help her get a job” more as along the lines of “by giving her a good reference”. Maybe telling her if you hear of an opening you think would suit her.

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  5. Eldritch Office Worker*

    Lw 3 – I actually don’t find this all that surprising! If you don’t respect personal boundaries, that usually shows up in more than one aspect of your interpersonal dealings.

    Reply ↓
  6. MassMatt*

    #2 congratulations on the new job, and I hope you continue your recovery from the bad one.

    I was so angered to hear that your boss/the owner was working at it only part time while you were putting in extra hours.

    This is her mess!

    Reply ↓
  7. JJ*

    I have an experience kinda like LW2. Felt unsupported, unappreciated, and was drowning. I actually asked my boss for a one-on-one where I was going to lay it all out and she let me go before we even got into it. Yes, chat, I asked for a one-on-one with my because I didn’t feel supported and appreciated and she basically said, “You’re right, there’s the door.”

    New workplace is SO much better. Supported, valued, appreciated, work/life balance respected and encouraged, cross training people so that nobody is on an island where they can’t take time off and disconnect is not just lip service, you name it everything is so much better.

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  8. Two-Faced Big-Haired Food Critic*

    LW3: Your problem was not bland. As others have said, what he was doing was undermining. He probably said it was always a joke, right? Huh-uh. It’s a joke when both parties are laughing*. And I’m wondering (haven’t read the comments on the original letter) if there were certain times when he did this, like right before a meeting or some time it was important for you to be cool and collected? He had to have been aware that it took you some time to recover. Or if not, then he was a clod and that’s bad too.

    *Example of being startled in a good way: Mr. Critic once left his car in airport parking for me to drive away. He’d left disk 1 of the White Album in the CD player, ready to go with Back In the U.S.S.R. So from my perspective, I heard jet engines, of course…gee, that tire screech was awfully close…OH! The guitar chords came strutting in, and I laughed. Because that was a good startle. And another reason it worked is because my husband knows me pretty well, certainly better than your co-worker knew you.

    Reply ↓
  10. Robert E O Speedwagon*

    A live rendition of me reading LW3’s update:

    “Ah, good for you!”
    “OK, he stopped. Wins all around.”
    “…well then. Good riddance.”

    Reply ↓
  11. Zelda*

    I’m afraid I don’t believe for a minute that it’s “just not feasible” to ban relationships between employees and customers in a bar.

    That said, I’m glad this particular situation turned out well for all concerned.

    Reply ↓
    1. Sigh.*

      Then I’m assuming you’ve never worked in a bar and/or restaurant situation, particularly those that are in smaller communities or less fancy/upscale. It’s kind of a free-for-all environment, at least it always was in my experience lol. Transitioning from restaurants – which at the level I worked at were truly lawless places – to even a retail position was a MASSIVE learning curve.

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      1. Zelda*

        I am aware that food service usually *doesn’t* set those boundaries. That’s a very different thing from saying they *can’t* set them. I’m looking for a pair of articles I read recently, written by a bar owner on what he does to protect his staff and keep things professional, and my search engine isn’t turning them up. I’ll post again if I can find the links.

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        1. boof*

          I think it depends; especially in a small town/community/circle, might not be feasible because everyone is either working at the place or sometimes uses the place and only hiring single employees is also not reasonable
          But it’s very reasonable to discuss with employees how to prevent unwanted comments from customers and how to handle personal relationships while “on the clock” to keep it professional

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          1. boof*

            (to clarify, by prevent unwanted comments I meant more like how the employer was going to discourage it and how to handle it if it happens anyway)

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          2. Nebula*

            Yeah, I think LW dealt with it well. Banning those relationships, especially in a small-town situation like this, where that might mean severely limiting someone’s dating pool, is going to cause resentment and employees hiding relationships from their boss. In the latter case, that would mean the employee then wouldn’t feel safe going to the boss if things went south, which is not a good outcome! Better to just encourage people to be open about it and be clear about boundaries.

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      2. Martin Blackwood*

        I lived in a town so small I could count the food establishments on one hand. The bar, the diner, the chinese place, and The Other One

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    2. SnackAttack*

      Eh, to me, that’s encroaching too much on the employees’ personal lives. I’d be annoyed if work was telling me who I was/wasn’t allowed to date outside of the employee pool. It’s one thing to ban relationships between coworkers, but pretty much anyone in the town could become a customer at the bar (or stop being one) at some point or another. Let’s say the employee starts dating someone else – are they never allowed to come in and grab a beer with friends? Or the opposite – what if someone partied a lot there in their 20’s, met the employee, then stopped coming in to save money or drink less or whatever?

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      1. Zelda*

        It’s about the order of operations– an employee’s date becoming a customer is an entirely different thing than a customer trying to turn the professional relationship into something else. If the personal relationship is formed elsewhere, in personal or public spaces like through mutual friends or mutual interests, that’s not a workplace issue per se. Short version, no one should be hitting on anyone at their workplace.

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        1. Annie2*

          But your proposed solution doesn’t actually address the problem. A “no dating customers” policy doesn’t stop customers from hitting on staff! You’re placing an annoying and unrealistic restriction on your staff to solve a customer problem.

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        2. SnackAttack*

          I mean, I know there are people who have an issue with it, but lots of successful couples meet through work with no discomfort whatsoever. Obviously there’s an issue with supervisors dating direct reports, and you can have rules in place to protect staff when there’s unwelcome flirting or harassment, but you really can’t stop people from talking and hitting it off. Plus, how would those rules work? “You can’t date fellow employees, and you can’t date customers. Unless you meet in one of the following ways I deem acceptable, in which case your BF/GF can subsequently become a customer.” Idk, I just don’t see how you’d avoid pissing your employees off.

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  13. Observer*

    #2 – Left a toxic Job

    I am *so* glad that you are happy in your new *normal* job! And your fiance sounds like a keeper, so it’s really nice to hear that you are soon going to be married.

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  14. Ex-Prof*

    #3, way to bury the lede.

    So, not such a nice guy, then. I’m not surprised; I worked with him all through my 20s.

    Reply ↓
  16. CSRoadWarrior*

    #2 – Glad you found a new job. It’s really sad when someone new to the corporate world think that this is normal. And I don’t mean sad that you didn’t know; I meant sad as in you had to endure it. I knew someone who just graduated college and thought “Amanda” was normal at work. But it is not normal. Glad you got out of there.

    #3 – Whoa. That last sentence. I am beyond words. But going back to the original issue at hand, as someone who startles easily as well, I would be pissed. Especially that this person was willfully doing it. It is extremely rude.

    Reply ↓
  17. WillowSunstar*

    LW4: Glad you were able to change desks.

    I would say it really, really depends on the reason you don’t like someone. As a woman who once worked in a job with a stalkerish male coworker, who I ended up having to go to the boss about because the guy was staring at me for minutes at a time without saying anything, I only got to change desks after we moved buildings a few months later. But yeah, sometimes these things do work themselves out.

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  18. TD*

    #3: “It’s the same thing as being tripped on accident vs being tripped on purpose. Both irritating, but one is usually followed by apologies and laughs and the other is rude.”

    Being tripped on purpose isn’t “rude” — it’s bullying, and possibly assault. This is further evidence that the writer is still giving people like Mr. “otherwise a nice guy” way too much benefit of the doubt.

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    1. Florence Reece*

      What a weird takeaway from that sentence. I’d suggest that maybe it can be all three. It’s certainly not *polite* to trip someone on purpose. Any reason to tear people down though, eh?

      Reply ↓
    2. magic*

      A rough analogy the LW used (and probably didn’t think about too deeply) to explain a distinction into why what happened to them is not “further evidence.” Sometimes LW certainly give us reason to point that out, but in this case it seems like an overly personal reading.

      Reply ↓
  19. foofoo*

    [i]But in the end, during Covid work-from-home, he was fired for asking another colleague for topless photos.[/i]

    Legit just screech-laughed at the schadenfreude.

    Reply ↓
  21. AnneMoliviaColmuff*

    I don’t know that I’d want to hear about a romantic interest’s “many breakups” from my boss…

    Reply ↓

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