my boss wants to be my BFF

A reader writes:

I started a new job around the time COVID-19 hit. To take the job, I moved about six hours away from home, so I was starting over in a new city and I didn’t know anyone other than a few friends of friends. I worked in the new city for a month, but when everything shut down, I returned back to my hometown to continue working remotely, as it was easier to be closer to my family and friends.

While my new boss, Janet, is really kind, she keeps mentioning that because I don’t know anyone in the city, when I come back we should hang out outside of work and she could show me around. At first, I thought this was a good idea because I wasn’t familiar with the city and it would be a way to meet new people, but she keeps bringing it up (“when you come back, we can go hiking, check out parks, etc.”). She has mentioned “hanging out” almost every week since we started working from home months ago. It’s making me really uncomfortable and I’m unsure how to respond.

Janet is a first-time manager. I’m a woman in my late twenties, and she is twenty years older than me. We are both administrative staffers and the only two people in our office who perform our duties, and I am the youngest person here. She has been here for almost 25 years and has mentioned she becomes “attached” to people and gets emotional when someone leaves the department, even if they are retiring or moving away.

I’ve always felt there should be boundaries between a manager and employees, so these constant messages from Janet make me uncomfortable. I am a shy person, and I would prefer to open up to people on my own terms, without the poking and prodding. I did have a really good relationship with my previous boss from my old company, but it was never to the extent where we would spend time outside of work with each other. Mainly we would grab coffee during the workday and walk for a bit or sit and chat. We still keep in contact, but we have never hung out socially.

Janet has offered to help me get set up in my new apartment when I return, even though I’ve mentioned my parents and siblings will be helping me. She also frequently says things like “I will be there for you as a friend” when I complete regular, everyday tasks.

I feel guilty for feeling like these messages are getting out of hand, because Janet genuinely seems like a kind person, but it’s making me anxious whenever she brings it up. I am scared to appear rude and tell her that I want to figure out the city myself, alone. I am in some ways dreading moving back to the city where the company is located, even though I was super excited to move before.

How can I navigate this type of awkwardness? I don’t want seem chilly or unpleasant, but at the same time I want to have a good work/life balance and do my own thing, without having my boss in my personal life.

You can read my answer to this letter at New York Magazine today. Head over there to read it.

{ 74 comments… read them below }

    1. Grits McGee*

      Oh was that the eco-yogi slumlord article? I didn’t read it because I want to save all of my precious free articles for Alison’s columns, but it sounded like a doozy from the title.

    2. RWM*

      As I was reading that, I kept thinking of how many AAM letters could have been generated by this couple!!!!

    3. Ermintrude*

      Shit, I’m lucky. I got a lease and a new part-time job in Sydney. This is a heck of an eye-opener.
      I want these 2 people to fall so hard, but it’s not their children’s fault their parents are nasty scum.

  1. Zombeyonce*

    If a person I actually wanted to be friends with were this heavy handed about it, I’d stop wanting to be friends with them pretty quickly. It’s frustrating when people are so oblivious to signals of disinterest and kind brush-offs; you have to treat them like a toddler and distract them with something else to get them to move on, but they always come back to it.

    It’s not going to be fun to have to use Alison’s scripts to get her off your back, LW, but I think you’re going to have to do it. I’d break the no-go-friendship news sooner rather than later because it’ll be much easier to do them when you’re remote than in-person and have to deal with her sulking around the office (because she definitely seems like the kind of person that will sulk or brood over it for a day or two).

    1. Amaranth*

      I don’t agree with Alison about leaning on it being ‘old fashioned’ because that phrasing seems to imply that OP also might think its silly and could be convinced that times have changed. I think I’d approach it from the angle that an appearance of favoritism could hurt both their reputations, maybe that she’s seen it before.

  2. Cringing 24/7*

    Ugh, I had an employee like this once – they were constantly asking to hang out after work and inviting me to go to social events, and I kept declining. Then one day they straight-up asked, “Aren’t we friends?” And I stared at them for I think a solid 5-10 seconds before responding incredulously, “No? I’m your boss.”

    It may sound a bit rude, but this person refused to take *any* type of “no” for an answer, and it just got to the point where I had to be straight-up about it. Although that was easier for me than it would be for OP because they’re on the other side of it. I love what Alison has suggested here. Good luck, OP!

    1. Uranus Wars*

      I have an employee like this.. We still talk about it on a semi-regular basis (probably monthly, and have for two years). I’m not “warm & fuzzy” enough for her (she’s been clear she think I am supportive as a boss, but she would like to know more about my personal life)…it’s exhausting.

      When I declined an invitation to her wedding (I had other commitments the same weekend) she told me straight up that her husband asked her if I was “one of those weird bosses that doesn’t want to be friends outside of work.”

      I mention it with your comment because she is a case similar to OPs…only as her boss the dynamic is very different. BUT even straight forward sentences like “I am your boss and do not like to cross boundaries” do not stick.

      1. Mimi Me*

        At my current company I’ve had 2 bosses. My first boss doesn’t share much about her personal life. It was 4 years before I even knew she had a son! She brought it up once while asking about my son (who was having some behavioral issues at school at the time). My current boss was originally a peer and got a well deserved, much overdue promotion. I’m much more friendly with him, as we had gotten to know one another over the years of working together, but he definitely dialed back with his promotion. Newer team members know very little about his life. I have to be honest – I love that my bosses put those boundaries up. It makes the moments where they do share something stand out – ex: my first boss only shared her personal life because I’d had to leave work several times to get my son from school. My frustration was something that was hard to miss and she brought up her son as a way to 1) help me realize I wasn’t alone in this and 2) to share some work benefits that had worked for her when her son was similar aged and behaved (EAP, Flex time, and FMLA). I felt seen by her in a way that I don’t think I would have if she’d tried to be be friends with the team. To this day, that conversation is one of my best boss interactions.

      2. Dumpster Fire*

        “Nope, I’m one of those good bosses who avoids putting my employees into awkward situations.”

        1. GammaGirl1908*

          Right. “Those weird bosses that [don’t] want to be friends outside of work” = people who get too much of their idea of how to manage from television and movies.

      3. Zweisatz*

        Oh, “her husband” told her that? Uhu.

        As you can see from the quotes I am dubious it even was her husband, but in the end it doesn’t matter – why would you share that with your boss?? I didn’t know people thought it was a good idea to neg their own manager.

  3. juliebulie*

    Janet sounds lonely. Desperately lonely. Which is not OP’s problem… but I wonder if OP knows another lonely person and could introduce them… No, no. I know this only works on TV shows, and even then only sometimes.

    It’s just sad that someone’s life is so empty that she tries to harvest friends from her workplace, and that the employees have to fend her off.

    I have seen before what it looks like when a boss is tight with one of her direct reports. I wonder if it would at all be helpful to explain this to Janet if she pushes back on OP’s gentle rejection.

    1. Mel_05*

      That’s not a bad idea. Something along the lines of, “I’ve seen how it can cause issues in the office, even when everyone’s trying not to, so I’d feel more comfortable…”

    2. Jaybeetee*

      The funny thing is, I know a number of people who’ve become close friends (not to mention romantic relationships) through work – including, in some cases, bosses and subordinates (friendships, that is, not dating). But it’s one of those things – when you need friends, it’s harder to make them.

      1. juliebulie*

        It can definitely be done without looking like a two-person clique. But Janet does not sound like the kind of person who can pull it off.

    3. MK*

      I agree that this is a very sad situation, a person must be cripplingly alone to decide that an employee 20 years younger whom they hardly know is a best friend. But there is really nothing for the OP to do other than what Alison suggested.

    4. Mimi Me*

      TV shows are where we see that blurring of lines. I’d love to see a show where the boss is kind, professional, but boundary setting. Either the bosses on TV are besties with their employees or they have boundaries but the boss is cold and unfeeling.
      I do have to admit, I got some definite Michael Scott asking Jim Halpert to hang out vibes from this letter.

    5. Wintergreen*

      I agree, Janet sounds a little lonely but maybe its just the examples given, she also sounds like she has some cabin fever…. hiking, parks, etc.

      It could just be that Janet is the type of person that throws out the ideas of “Lets do X, it sounds fun!” without ever having the intention of following thru with X. You know, the ones who go “It’s been a stressful morning, we should go out for drinks after work!”, after work rolls around… “I’m going home and vegging out in front the TV. Have a good night!” with no mention or thought to the drinks they themselves originally brought up. I’ve known quite a few people like this and it could be something that’s missed when it’s a remote situation like this pandemic that becomes glaringly obvious when in person.

      1. Elsajeni*

        Yeah, especially since it sounds like this started after everything shut down and the OP went to remote work, and wasn’t an issue during the month that she was working there in-person before that. That may actually be a good sign that Janet won’t be this pushy in person — by the time OP is there in person again, Janet will be able to socialize with her actual friends again and the cabin fever will hopefully have passed! But the constant talking about it is certainly still a problem in the meantime.

  4. Mel_05*

    What a nightmare!

    I’ve had some pretty chummy work friends and even that can be a little much or me. But a boss!
    Nope.

    I’m glad my boss is friendly. I’m glad that our department team building exercises look a lot more like we just took off work early and hung out for a few hours. But I am equally – no – I am even more glad that my boss has never tried to be my friend outside of work.

    1. MissDisplaced*

      In my 20’s I became really close friends with my manager who was about 10 years older than me. We’d go sailing together and hang out. To be fair, she also hung out with and took many other people from the office sailing too, though in hindsight, it probably didn’t look good for us to be so chummy. I’m still great friends with her some 25 years later and consider her to be the big sister I never had.
      It would’ve been extremely sad had I not made that friendship or had her in my life.
      But yeah.

      1. jenkins*

        Yeah, I think it’s the sort of thing that works out beautifully once in a blue moon – but even then it has to grow slowly and naturally from the working relationship you start with (and there’d always be a risk of favouritism, real or perceived). For one person to be pushing the friendship as hard as LW’s boss is just bleeeeee. My shoulders are up round my ears just reading it.

      2. ThisColumnMakesMeGratefulForMyBoss*

        I have one friend who has been my manager at 2 different jobs, and while we don’t hang out often, we are real friends. But I realize that this dynamic is a rarity, and most of the time is not a good idea.

  5. Red Tape Producer*

    My last manager actually hired me because she thought I would be good friend material (found out months after). I realized really quickly that if I wanted to get delegated work I had to attend her after work functions and “lunch time adventures”, someone else hired at the same time held firm on work boundaries and suddenly was never assigned anything.

    It was not worth it, I wish I had put up with getting shut out of assignments over getting myself entangled in her personal life. It was incredibly difficult to get her to give me a fair reference when I applied for an outside promotion and, judging by the fact she blocked me on every social media platform and refuses to acknowledge me to current staff, I’ve lost that reference forever. Learn from my mistakes, get the awkward boundary discussion done early!

    1. allathian*

      I’m so sorry. I hope you have someone who wasn’t your boss at that company who can be your reference instead. I sure hope you’ll get at least HR to confirm your employment dates.

  6. MissDisplaced*

    Hm. Well, I’m mixed on this. Probably this is all feeling much weirder than it normally would because… Pandemic.
    In the normal scheme of things, you certainly might have coffee or lunch with your manager weekly, or you know, be doing some work-related things together that sometimes bridge the gap between work and social friendship (walking, yoga, work dinners, volunteering, employee parties, events, travel, etc.) depending on your company’s culture and amenities.

    Probably, your manager is just really feeling cut off from human interaction and it’s showing more than normal.
    So, be kind! Allison’s script is good if it really is a case of her being too chummy and not wanting to blur the lines.

    1. fogharty*

      I agree with you… this is most likely pandemic related. Also perhaps Janet is concerned you might prefer to stay in your hometown even after… all this… and is overcompensating.

      I think it’ll drop off eventually. If not, then Alison’s scripts are a good place to start.

    2. Lena Clare*

      Yes, totally agree. This is how I see it too. And being kind will help smooth things over, in case Janet is hurt – which she may be.

    3. Ask a Manager* Post author

      Foe what it’s worth, I’ve received a pretty steady stream of letters about bosses like this for years, long before the pandemic. So it *could* be pandemic related in this case, but there’s a decent chance that this is just how this boss is.

    4. Reba*

      I think it’s just how she is, but I also think the fact that none of these hang-outs have actually happened is contributing to the repetition.

    5. OP*

      Yes, the pandemic has definitely made for some different changes in workplaces. I am unsure if this how my boss is regularly, considering I haven’t known her for very long, but maybe it will taper off once places start opening again.

      Alison gives great advice–I was really nervous writing in (long time reader, first time asker) but everyone here sounds super supportive. Thanks for chiming in!

    6. Person from the Resume*

      I don’t know. I have dealt with this in my personal life. People wanting to be my friend but I just don’t like them that much even though there’s nothing wrong with them. I just don’t click even if they think we do. I feel sympathy and pity for someone trying hard and don’t want hurt their feelings, but I have learned you’ve got to just do it.

      This is a little weird because the LW’s boss is talking about future hangouts, but also laying the groundwork for them. I think this being work does allow for the LW to declare firm boundaries between work and outside work friendships.

  7. Sara without an H*

    Hi, OP —
    I agree with Alison’s advice, and with pretty much all of the upstream comments. If you can stand it, maybe you could offer to do an occasional lunch, as well as coffee? In either case, you should be careful about the kind and amount of personal information you share. Be friendly, but not overly confidential.

    I have one other suggestion: start documenting now. It doesn’t have to be elaborate, just set up an online account (I use Google Drive) and make notes of your boss’s repeated “friend” requests. With luck, you’ll be able to get her to back off with several applications of Alison’s scripts. But if she won’t back off, or if she gets angry and tries to take it out on you, it will be useful to have the documentation, in case this all winds up in the HR office.

    1. introverted af*

      Also, documenting it just helps you not gaslight yourself – or rather, it gives you an accurate picture of what happened, so you can weigh if this is really worth a big push to deal with or if it’s a minor annoyance that just became BEC to you. (And in the terrible situation that someone ELSE tries to gaslight you, then of course it helps there as well).

  8. Anna*

    I agree with others that she might be lonely/it could very well be pandemic related. (I have a lot of vague offers/plans to meet up with non-work people when this is all over.)

    This does remind me of the time a coworker found a new job at another place and quit because they were sick of our boss trying to be BFFs (it helped that new job had better pay and fewer phone calls to deal with). She was not of the best people on our team and higher-ups even came up with a counter offer to try to keep her, but she was just Done. I couldn’t blame her.

  9. Partly Cloudy*

    Oh, I simultaneously feel exhausted on behalf of the LW and embarrassed for Janet while reading this. I definitely think COVID could be exacerbating the situation but Janet is probably kind of needy or lonely anyway (she gets clingy and emotional when people leave, and that was presumably pre-pandemic). Hopefully these scripts do the trick because things will get awfully uncomfortable for one or both of them if they don’t.

    LW, this is drastic, but is it possible to… not move? Since you’re successfully WFH anyway? Or if moving away from your hometown was part of the appeal in the first place, can you move to a third location and continue WFH?

    1. OP*

      Hi! Unfortunately, it’s probably not possible to stay in my hometown–we’re in the government sector, and the only office is located in this specific city. Who knows though, with a lot of companies moving towards telework, there might be a possibility that I might be able to work remotely, but the overall work culture here seems to be rigid, with a preference to work in person. They’ve made an exception in the current situation, but it’s been a huge adjustment to the entire company.

    2. Malarkey01*

      I’m a real introvert that’s been WFH for over 10 years when not on travel, and after almost 6 months of quarantine even I’m getting effusive on work calls saying I can’t WAIT to get together for drinks! And making broad future plans for movies and hikes and dinner with people I’m sort of friends with… I can’t imagine how it is for people that regularly thrive off contact and occasional get togethers.
      I’m envisioning a weird quick flurry when “released” again that fades back to thinking up excuses for why we don’t hang out (kind of like the initial flurry of zoom happy hours and block party dinners where we sit in our own driveways and wave at each other that thank god stopped pretty quickly). Hopefully it will be easy to have a quick chat with Janet and it turns out her expectations weren’t really this high.

      Spoken as a hermit that still would like an occasional break from her cabin on the mountain.

  10. KimberlyR*

    LW, if this doesn’t seem to apply to the situation, ignore the comment below:

    Janet has been there so long that she might be an Institution there. By that, I mean that she may be like this with everyone. She may fulfill the “mom” role in the office (not that I think she should or there should be someone like that. I’ve just known many people who voluntarily took it on) and/or be known as that warm, fuzzy person everyone loves. Since she will be acting way more friendly to you than you may to her, plus you mentioned that you’re shy, you’ll definitely want to take Alison’s advice about having warm interactions when you’re back in the office, with her and everyone else. You don’t have to be overly effusive but keep a warm tone and friendly smile so you don’t come across as cold or mean, when you’re really just shy and trying not to be your boss’ BFF. You want the office to see you for who you are and not assume otherwise because you haven’t fallen in with your boss’ chummy plans. I really don’t think you should have to do any of this! (You should be able to be your genuine self without extra effort to appear friendly) but you may end up having to, just to convey that you are a friendly person without wanting to be IRL friends. Good luck!

    1. OP*

      Thank you for this! Most people here actually work as long as my boss has, if given the opportunity (it’s the government), so I am unsure if this is how everyone is or if it’s just a regular thing because they’ve known each other for so long.

      I will most definitely try to stay friendly with everyone–I flit back and forth in communication with all the supervisors so it would be very awkward otherwise!

  11. Laura H.*

    Agree on the friends vs. friendly. Never have been a manager, but I’m naturally very warm to people and have a friendly nature. Even if I think I have a good grasp on this, I still want to be careful- I get the attachment thing, it happens because I’m a people person. However, it’s tempered by the fact that I want to be mindful of boundaries. Helping or accepting help moving from a colleague is definitely over a line.

    Good luck OP.

  12. OP*

    Thank you very much Alison for the advice, and for publishing my question! I hope I haven’t scared too many people with my letter–seems like a lot of people have the same consensus that I should make myself very busy, and be straightforward with setting boundaries towards my boss’s attempts of spending too much time together socially. I’m hoping these tips will work.

    I will try and reply to the comments above as best as I can. :)

    1. juliebulie*

      I have to say that over the years, “busy” has never worked particularly well with the kind of people who were already not taking the hint. And the longer I claimed to be “busy,” the more uncomfortable I got and the harder it was to be more direct.

      So if you think that “busy” is not going to do the trick, it might end up being easier to use Alison’s scripts sooner rather than later. I doubt you will be the first person to tell her that you like to keep your work life separate from your social life.

      1. Sharon*

        +1
        It’s perfectly reasonable to want to keep professional and personal separate. But not everyone is like that. Just tell her straight up!

        1. valentine*

          “busy” has never worked particularly well with the kind of people who were already not taking the hint.
          She’d probably see “busy” as a problem to solve. And OP may have to be less forthcoming than they want to. Some people can hear details like who’s helping you move and go on with their lives. This boss hears only opportunities to shoehorn herself into your life.

          You might want to read the letter and update where the manager wanted the OP to “adopt” her and, when OP shared personal plans, the manager invited herself.

          1. Arts Akimbo*

            >She’d probably see “busy” as a problem to solve.

            I cannot help but think of that most spectacularly train-wrecky episode of The Office where Michael Scott faked a corporate overtime assignment in order to get Jim and Pam to cancel their evening plans. Then he faked a phone call to corporate where he announced he wasn’t going to make his people do this! Then told all the employees to go home, except for Jim and Pam, who he invited to dinner at his condo. With Jan. Because he knew they didn’t have plans!! PROBLEM SOLVED! Trainwreck begins.

            Not saying all workplaces are The Office, but there are way, way too many iterations of Michael Scott out there. I concur with the voices that say “use Allison’s scripts sooner rather than later.”

  13. Not A Manager*

    The only alteration I would make to Alison’s script is maybe to lean more heavily into how much you like her and would love to be friends under other circumstances.

    She sounds like someone who could easily get her feelings hurt and, this is just my instinct here, but she sounds like someone who could sulk or get passive-aggressive too. I’d take your usual “it’s not you it’s me speech” and dial it up a few notches. “You have been so kind and supportive to me, and under other circumstances I would really LOVE to have a friend in City who could show me around and hang out, but I’ve seen how difficult it can be when people develop an outside friendship with their boss. Thank you so much for being so generous about offering your time.” I would really emphasize that you are very, very sad not to be able to hang out with her.

  14. Allonge*

    Ooooh. Not good.

    She reminds me a bit of one of my work-friends, who is very interested in people and very social (no conversation shorter than 15 minutes!) and asks a lot of questions and knows not just everyone in a 300+ staff company, but the names of all their spouses, partners and kids and where they live and is a nice person but can be reeeeally exhausting. Like, way way exhausting.

    And she wants to be very helpful to everyone in any situation (she was organising a work event, got into an armed shop robbery on the way to the event and was still offering to drive people home after the event – not two who live on the way home for her, but everyone and anyone. Just randomly! And our town has excellent public transportation, lots of taxis and armed robberies are very rare).

    Anyway, my point was: this is exhausting in a peer, but as a boss? Even shades of it could be too much. Do try Alison’s approach and shut this down – it will not stop on its own. Sorry, OP, this is tough. Explaining that someone is Too Nice TM is difficult, even to ourselves.

  15. Ailsa McNonagon*

    Oof. OP, I feel for you. As a manager now I try to keep clear boundaries whilst still being friendly- it’s so much harder to give clear direction and honest feedback to your mates than it is to your staff!

    Early in my professional career I made the mistake of being ‘friends’ with the very pushy, deeply unpopular team leader- it ended up in a whole mess of meetings and borderline disciplinary action (against her, not me), mediated by the service manager. If someone is TOO desperate to be friends, that’s important information you shouldn’t ignore!

  16. Ermintrude*

    I see myself in an alternate future where an amazing woman on staff in the organisation I was volunteering with and was my mentor at the time hadn’t very kindly explained why she wasn’t going to be friends with me, and how her role brought her into contact with others who also wanted her in their lives, so I got the clue and several years later have developed healthy, strong friendships.
    Alt-me would be Janet-level intense for my entire adulthood.
    HAAARRRGGGHHH. Bullets not fired!

  17. Duckles*

    Semi-related: How do you handle when you become friends with a coworker and one of you is promoted faster than the other? I started slightly ahead of a woman in my prior company and we had a lot in common and quickly became casual out of work friends where we’d go to each other’s birthday dinners and some sporting events. I was also promoted more quickly than she was. As I progressed it got to the point where sometimes we worked as peers and sometimes I assigned her work, and also sometimes gave her formal reviews (but no hire/fire/pay authority). What’s the best way to handle this situation without losing a friend?

  18. Root beer float*

    Man, people here are harsh! I know a ton of people who say stuff like “We need to get together sometime!” “Let’s have dinner sometime!” and then never actually follow through on it. To a lot of people it’s just a friendly thing to say without any real obligation. To me it’s a very normal part of small talk to say “We should have lunch sometime!” and the other person says, “Oh, totally!” And neither person attempts to pick a place or a date so it’s just a hypothetical friendly thing to say. If that’s what she’s doing, it would come off extremely strange to try to set boundaries and have a serious conversation when they’re just doing some friendly chitchat with no intention of becoming your best friend. I would just say “Oh, for sure, we should have lunch sometime!” and save the awkward conversation for if she actually tries to get you to do stuff once you live in the same city and it becomes clear that she’s not just being friendly/chatty.

    1. Gymmie*

      I hate that. If someone tells me they want to have lunch, then I want to have lunch. Just say what you mean “see you around!”, “good luck!”, “great seeing you!”

      If it’s someone I actually wouldn’t mind getting together with, then…I’d feel a little peeved if I tried to reach out and they were always busy.

    2. delicate&lustrous*

      I agree, especially in the current circumstance. She may very well be looking forward to a return to normal (lots of people are longing for that!) and just off-handedly making comments that wouldn’t be as obtrusive if OP was actually in the new city. Maybe she’s suggested 5-10 different things because she can do zero of them currently and just suggests whatever seems friendly at the time, but if OP was actually there, they’d go out for coffee together or a lunch or something work appropriate and that would be it on the invitations for a while. Like maybe the ideas are piling up in her head because she can’t act on them.

      Or maybe she’s getting ready to stomp all over OP’s boundaries, who knows. But I wouldn’t start stressing about it until I was actually back in the office, if I were OP.

  19. Karia*

    I’ve had a couple of bosses like this in a row. What’s been horrible about it is that they have taken not wanting to be mates as an insult. One brought up in my review that I wasn’t ‘friendly enough’. I was confused about this as I had warm relationships with my colleagues. I eventually realised she meant with her! But good god, she talked *all day*, often about deep personal topics. I don’t have that social bandwidth with people *I like*.

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