my boyfriend is pressuring me to act as a big sister to his trainee

A reader writes:

My boyfriend describes his coworkers as “family,” which I can’t really relate to because I like to keep my work and my personal life separate. In a given month, they’ll hang out a few times as a group over the weekend. I am there sometimes when it’s on the weekends. However, it is not my personality nor my desire to be close with his work people.

My boyfriend insists on my congratulating his trainee on her work achievements and wants me to act as a big sister-type figure to her. (He is officially her “trainer,” but not her manager; they both have a manager in a position higher than them who is in charge of overseeing them both.) I don’t feel comfortable with that. How do I approach this without coming off as cold?

That’s pretty odd.

It’s certainly your boyfriend’s prerogative if he wants to treat his work relationships that way, but it’s strange that he’s insisting that you do too.

All you can really do is address it directly and explain to him where you’re coming from. I’d say something like this: “I feel strongly about not mixing work and personal relationships. I’ve seen it lead to too many problems with professional boundaries, or if someone loses their job or has a disagreement with a manager or coworker. It’s of course your call to handle your work relationships however you want, but I’m not comfortable mixing work and friendships like that, even when it’s your job rather than mine. I’m definitely up for hanging out with your coworkers on occasion, but I’m not really up for being in a big-sister-type role to Jane.”

You could also explain that you think it’s asking for drama if Jane ends up not working out, or has a beef with him or their manager. It’s reasonable to say, “I’d rather just not open to the door to any of that, although of course I’m glad to continue being friendly with her when I see her.”

From there, he either respects where you’re coming from or he doesn’t. If he doesn’t, there’s a larger conversation here for the two of you to have — about how you each see the intersection of work and life, as well as how you’ll navigate differences between you.

Read an update to this letter here.

{ 175 comments… read them below }

  1. BRR*

    I’m not even sure what he wants you to do. Also does this employee want a big sister? I’m ok with a trainer, a manager, a mentor, but if someone suggested their SO be a big-brother type to me…no.

    1. Turtle Candle*

      Yes, I was just thinking that if I was new at an organization and my mentor/trainer seemed to be pushing me towards being besties with his girlfriend, I would be genuinely creeped out. It would make me wonder why he wanted to enmesh me in his personal life to that extent. And I work at a very friendly company where coworkers hanging out together a few times a month is entirely normal!

    2. stiveee*

      Yeah, this seems paternalistic and weird. Would he suggest that a male employee needs a big brother?

  2. A Dispatcher*

    What the what? And I say this coming from a field that’s super insular, where we all tend to hang out together because of our hours, our whacked out sense of humor, not a lot of people understanding our stories and stress, etc etc. So it’s not like I don’t get the whole coworkers are family thing, trust me…

    Significant others don’t count though! No one wants to hang out with their SO and his coworkers and constantly talk about work stuff, that’s just boring for the SOs who are not employed there, and frankly, is rude. It’s very excluding.

    As to this specific bit: “My boyfriend insists on my congratulating his trainee on her work achievements” I have a lot of issues with this. BF probably shouldn’t be talking about his trainee’s work achievements very specifically to you in the first place (outside of either venting or being happy that his work is going well) and definitely should not be asking you to SHARE with his trainee that he volunteers this type of information to you. She might be really uncomfortable with that to be honest. If she won some major award and you quickly congratulated her sure, but “hey congrats on picking up on how to do TPS reports” (or a remark about something equally as mundane/everyday) might come off as creepy and weird. She may be thinking how odd it is that BF talks about her so much.

    1. Myrin*

      Agree wholeheartedly. Also, to your last point, we don’t even know if the OP is in the same industry as her boyfriend. I’d guess she isn’t, since she probably would have mentioned that, so she probably doesn’t have the experience or knowledge to even appropriately judge trainee’s work achievements (apart from really obvious things like you say, like an award or something similar). This is so weird all around!

    2. Sadsack*

      Yeah, I would feel weird knowing that my trainer talks about me in such detail at home. It probably wouldn’t be surprising if he mentioned that I won employee of the month, but minor general achievements are not something I want to hear about from a coworker’s SO. What about mistakes, is OP supposed to comment on those?

      1. Cath in Canada*

        My parents are both high school teachers, and they constantly talked about kids they taught when they got home from work. I remember suddenly realising that my teachers probably talked about me at home, too. ICK!

        1. YaH*

          We tend not to talk about students unless we’re with another teacher. Muggles don’t get it. :)

            1. Buffay the Vampire Layer*

              Very true. Both sets of my grandparents were teachers married to teachers. My uncle is a teacher married to a teacher. My generation is the same, I’m a lawyer married to a lawyer and both of us have two parents who are lawyers. I think we all need to branch out a bit more.

              1. Elizabeth West*

                I think it’s about who you meet all day. That’s one reason celebrities tend to marry each other–they never have time to just hang out and meet a wider variety of people.

                1. Cath in Canada*

                  And I think the matched vacations help, too. It would be frustrating for a teacher to be married to someone who only gets a couple of weeks a year, and frustrating for the spouse that the teacher can only ever take their vacation time when the schools are off and everywhere’s busy and expensive.

                  (my parents are one of three pairs of married teachers in my (small) family – the others being my maternal grandparents, and my auntie and uncle)

  3. Bend & Snap*

    That’s so flipping condescending to the trainee. I would be so uncomfortable with a coworker’s girlfriend in a cheerleader role. Weird.

    Also any organization that says they’re a family would make me want to run away. I have my own family.

    1. Snarkus Aurelius*

      No joke.  I’m as friendly to my family as I am to my coworkers, which is to say I’m not that friendly at all.

      If I know you and genuinely like you, then yes, we’ll be cool.  But I’m not going beyond cordial just because we’re thrown together by chance.  I certainly won’t be telling you my deepest, darkest thoughts and secrets.  I don’t care how much DNA or office space we share.

      My sister is constantly disappointed in my lack of interest in family drama so if my coworkers think I’m family like the Tanner family, then they’re in for a whole lot of disappointment.

    2. pomme de terre*

      I had a college professor who gave us the advice that anything that is not your family that tries to tell you it is your family is trying to take advantage of you.

    1. NickelandDime*

      Yes. Something about this…is not right. OP needs to ask more questions about this, and her boyfriend’s working relationship with this person.

    2. TheOP*

      He recently became a trainer for the first time in his life, so he feels he is responsible for her (his trainee’s) success.

      1. Artemesia*

        Does he act in this suffocating friendly friendly way with male subordinates? This one would have my spidey sense tingling. Sir Galahad and all that.

        1. TheOP*

          Yes he does, but the male subordinates aren’t his trainee so he doesn’t pressure me as much with them. Just his own.

          1. ToxicNudibranch*

            Do you think he’ll be receptive to you telling him this isn’t how Things are Done? His job is to train, and perhaps to mentor, but certainly not to try and manage or influence his trainee’s social interactions (or yours, for that matter).

            If not, tell him anyway.

      2. OfficePrincess*

        I get feeling responsible for her success, but that is best handled by coaching, offering feedback, and looping the manager in if there are concerns, not having his SO (aka an otherwise total stranger) treat her like family. That just reinforces a total lack of boundaries and a skewed view of what the workplace should be.

      3. Myrin*

        Maybe I’m not seeing something obvious here, but what does his trainee’s success have to do with you?

      4. stiveee*

        Then he should be her big brother, but it sounds like he wants to push the emotional labor onto you because you’re female and therefore he expects you to be a caretaker. He also has a weird, paternalistic relationship with his trainee. I think he needs to step back and think about how he treats/views the women in his life.

    3. Adonday Veeah*

      I’m wondering if he’s either unfamiliar with office norms, or possibly this trainee has tried to get a little too cozy with him for his comfort, and he’s trying to insert “girlfriend” in there as a buffer? Just some thoughts…

      1. manybellsdown*

        So, my ex-husband used to bring me up in conversations with female co-workers he was hitting on as a “plausible deniability” thing. Like, if they got uncomfortable he’d go “Not hitting on you! I have a wife!” If they didn’t get uncomfortable, of course, he’d totally go for it.

        He’d also try to get me to be friends with his “friends” aka “co-workers he was hitting on”. This letter is giving me that vibe. It might be just me. But there it is.

        1. Van Wilder*

          I cannot defend this position. It makes no rational sense. And yet, I feel it. On a gut level.

          1. Annie*

            I absolutely agree, I get that same feeling. I would be weirded out if my trainer at work was doing this, although I probably wouldn’t be comfortable saying anything if I was brand new to the company.

  4. Myrin*

    Apart from the general weirdness of all of this, I’m also wondering about the simple logistics – when and in what kind of situation could the OP act as this mysterious sister-figure? She says she has no desire to be close to these people (not just the trainee, but all of the boyfriend’s colleagues) and the only time she ever comes into contact with them is during their group meetings. I have a hard time imagining how that kind of very sparse contact could establish the kind of relationship that is sisterly – OP is only “there sometimes”, so I’d imagine something like twice a month, maybe even less, and it’s always a whole group of people where it’s probably not super easy to get close to one single person.

    But I feel like I’m thinking too much about this since the OP doesn’t have any interest in these people anyway. And to be quite honest, I’m giving the side-eye to the boyfriend here. Surely he has figured out by now that the OP doesn’t share his stance on work and private relationships and doesn’t even care about his regular coworkers – why on earth would he think she’d form a relationship that is even closer than the regular meetings she isn’t interested in with a random new person?

  5. Stranger than fiction*

    The whole thing is so incestuous to me. What the heck kind of industry/profession do they work in?

    1. TheOP*

      OP here, it’s a small recruiting agency. Tight knit group – about 6 people in that office, and less than 50 people overall.

      1. The First Church of Appliantology*

        A number of people seem to be rushing to the conclusion that the boyfriend is putting the make on the trainee. That’s certainly possible, but I think that the Occam’s Razor “simplest solution” is that your boyfriend is kinda clueless about the inappropriateness of what he’s asking.

        If it were me, I’d just tell him “I’m sorry, but I can’t do that.” If it helps, I’m sure that AAM has helped to validate your feelings that there’s something vaguely ‘off’ about this.

  6. MashaKasha*

    Okay, here’s the first thing that crossed my mind… And I admit I am of the “let’s think of all ways this can go wrong” mentality. Suppose OP gives in and becomes a big-sister type of mentor to “Jane”. And then suppose, heaven forbid, things do not work out between OP and her boyfriend. As in, they split up. Hope they never do, but these things happen. What happens to OP’s mentorship of Jane then? (whatever that entails – I am honestly also pretty confused about what he wants OP to do.) Does it end immediately? Does it awkwardly continue? Does the boyfriend need to find Jane a replacement mentor? The point I’m trying to make is, 99% of the time, I don’t believe that bringing a SO into a workplace situation is a good idea. (The 1% being something like a wife of a college president giving dinners for the faculty – and honestly, I don’t know how they even do it.) The two just do not mix in my opinion. Just like Jane’s employment, a relationship or a marriage can go south at any time, and it’s best not to bring any coworkers into that mix.

    Also, do OP and her boyfriend work in the same field? If not, then it’d be odd for OP to be mentoring Jane in her work, including congratulating her on her work-type achievements.

    A very bizarre request all around, and not something I’ve encountered with any of my SOs.

    1. TheOP*

      We do not work in the same field. I am ok with congratulating them when we hang out, but to tell me to personally email her at her work email just seemed odd and over the top to me.

      1. Artemesia*

        It suggests your boyfriend has significant failure to be professional and rather poor judgment. Yikes.

      2. literateliz*


        From the letter I assumed he meant congratulating her when you two see each other, but emailing her at work? Noooo.

        Another community I am a part of has been having a great discussion recently about the idea of “emotional labor,” and this and the way you described it below (the “boss’s wife” role) remind me strongly of that – you’re supposed to perform unpaid labor to support him and help him succeed at his work. The whole thing reeks of 1950s sexism to me. I can’t quite verbalize exactly why it seems so gross to me on both a professional and personal level – it’s not just about keeping work and personal life separate, it goes beyond that.

        1. So Very Anonymous*

          I have an emotionally laborious job and am curious now about this conversation — would you be OK with sharing a link?

        2. themmases*

          This is a great point! I wonder it often when my partner is stressed about work and I have to talk him down, or when I do extra stuff around the house because he’s on call: where’s my cut? I feel like a negative externality of this company’s staffing decisions sometimes.

          In the case of the OP’s boyfriend– even if this approach were going to work, which it isn’t– why would she agree to do part of his job for free? Why would she email this trainee from her own desk, on the clock at her own job, even if it were going totally set them up for success?

      3. A Dispatcher*

        Whaaaaat? I’m sorry but your boyfriend is losing it. He might just be lost in excitement over training for the first time but you need to tell him to step back and reevaluate. This is insane and will come of as super creepy!

      4. Snarkus Aurelius*

        Emailing her at work to congratulate her on a work accomplishment?

        Yikes. Your boyfriend needs better boundaries. I get this is his first time training someone, but professionalism trumps his personal investment.

        Sounds like he needs to learn how to be a trainer.

      5. AnonInSC*

        No, no, no. I also thought he was asking you to make a point to say something when you saw her at these weekend gatherings. No way is emailing her appropriate. He needs some professional mentorship himself. I’m sure he’s just a great guy wanting to provide all the encouragement he can.

        Not to mention, if I was the trainee – I would be skeeved out by this.

        1. Turtle Candle*

          Yeah, I had been envisioning that when they were spending time together, casually saying, “Hey, congratulations on X!” Which would still be odd and boundary-violating to me, but at least could be semi-natural. Emailing her directly is a whole ‘nother ball of weird.

      6. Sadsack*

        I am willing to bet that your boyfriend’s and/or the trainee’s boss would not be happy about that and would discourage it.

        1. Sadsack*

          Furthermore, I hope that he gives her feedback in a professional, nonemotional way. What I mean is, I hope he doesn’t act overly excited and speak to her like she is a child when he is giving her feedback. Something about the fact that he thinks she needs extra encouragement from you is making me wonder how effective he is at giving feedback to her.

      7. ImprovForCats*

        Yeah, that’s weird. I could kind of see it if maybe he just wanted you to make a point of saying “I hear the new Teapot campaign you were working on is going really well, that’s great!” but anything beyond that is definitely over the top. I think if I were the trainee, I’d be baffled by that, and then feel uncomfortable around you the next time we met, since apparently you guys were discussing me at length!

  7. LBK*

    I don’t even understand how you would do this if you two hadn’t already naturally formed that kind of relationship – if she’s not already making efforts to spend time with you and confide in you she’s probably not going to take kindly to you forcing yourself into that role. You can’t assign someone a new friend and you definitely can’t assign them a new friend that they trust enough to consider a big sister.

  8. AcidMeFlux*

    I hope I don’t come off as looking evil here, but could BF have a crush on trainee, and be using you as a buffer/watchdog so it doesn’t go farther? (I’ve seen stuff like this a lot…)

    1. TheOP*

      No, that is definitely not the case. I am thinking he thinks he needs to act more as a “mentor” now that he became a trainer, and sees this trainee as someone who looks up to him so that I should be nice to her. He calls it, being the “boss’s wife” type of role. While I am as nice as I can be when we hang out, I am not down for having a close relationship.

      1. The IT Manager*

        So, you think he is conflating “big sister” with female mentor?

        The whole big sister thing is confusing to me, but I was wondering if he somehow meant mentor. Do you think it might be for the female perspective either to get you to talk to “female things” he doesn’t want too or to provide her a female role model because he thinks you rock professionally speaking.

      2. The Cosmic Avenger*

        Wow…I’m pretty close to my boss, we actually carpooled for a few years before he became my boss. And I know his wife socially a bit, but she has NEVER asked me about work, and I would think it was really weird if she did more than make the typical small talk about my work.

        Your boyfriend is not only so far off base that he’s not even in the same stadium, I think this would weird out the trainee, too. The only way this could even remotely work is if you worked at the same company that they do, and even then, she’s not your trainee.

      3. Ask a Manager* Post author

        You might point out to him that the boss’s wife is supposed to maintain good boundaries — not email her husband’s employees to congratulate them on things. A boss’s wife who did that would be the topic of a letter here, because the lack of boundaries would make everyone uncomfortable.

        Also, he’s … not her boss, so there’s a new, additional layer of weirdness.

        1. Adonday Veeah*

          “Also, he’s … not her boss, so there’s a new, additional layer of weirdness.”

          Very this.

        2. Jane the Teapot*

          Also, OP is a girlfriend not a wife. Therefore asking her to take on “boss’ wife” responsibilities is also out of line.

          1. hbc*

            Yeah, OP, if he wants you to act the “boss’s wife”, tell him that there are two words in that phrase, and neither applies here.

            That’s before you get to whether this is actual appropriate behavior for a boss’s wife. I was going to suggest that this sounds very 1950s, but even then Mrs. Boss would be bringing in treats or hosting dinners, not calling up the girls in the steno pool.

        3. Splishy*

          I can see the trainee’s letter now…

          Dear AAM:

          I’m a new hire in training at a small company with a very close-knit “family” culture. For example we hang out a few times a month on the weekends.

          My problem is with my trainer and his girlfriend. Out of the blue, the girlfriend started emailing me on some small workplace matters, like “good job on meeting the TPS report deadline” type stuff. I’m a bit freaked out because we’ve barely spoken except for a few weekend gatherings and things like TPS report deadlines just don’t come up in casual conversation — it’s not like I won the coveted Golden Teapot award for Excellence in Teapot Innovation!. So she has to be getting this information from him.

          It’s hard to explain, but in addition to being slightly condescending (like a pat on the head and a Good Job biscuit), these emails have a strange “forced” quality to them. It’s like she’s just doing some required task because he asked her to, not because she really likes or cares about me.

          What can I do? Apparently my trainer is discussing me and work with his girlfriend and — more worrying — asking (maybe forcing?) her to send these emails. It seems all sorts of wrong and creepy.

      4. Amber Rose*

        I think he watches too much TV.

        I have had a lot of bosses, and the closest relationship I had with any of their families was a friendly greeting at parties.

        1. The IT Manager*

          He watches too many 50s eras TV reruns. “Boss’s wife” is a sexist remnant of the past but even then she invited people over to dinner and cooked for them and didn’t talk about work except superficially.

          1. Amber Rose*

            Yeah, that. I was thinking of those old I Love Lucy type sitcoms. Not exactly a good basis for real life.

            OP, if he buys you an apron and/or a poodle skirt, run away! =P

          2. TheOP*

            We just finished a marathon of Mad Men. But even Don Draper’s wives weren’t active in his work life aside from Megan who DID used to work there.

      5. MashaKasha*

        I’m not sure that “boss’s wife type of role” is a thing. I barely even met any of my bosses’ wives in my 20+ year career.

      6. LBK*

        But being the “boss’s wife” in that capacity isn’t usually said in a good way – people generally don’t like when they have a relationship with their manager’s SO because it’s fraught with complications. It’s usually a phrase associated with an eye roll and a fake smile as you make small talk with someone you’re forced to be nice to out of obligation because you don’t want to piss off your manager.

        Unfortunately I’m not sure how to go about addressing this with someone who probably has close relationships with all of his superiors based on the way you’ve described his office. Are there any personal examples of things going south that you could draw on? I know it’s tough though since people almost always think they’re the exception to the rule when it comes to mixing personal and professional lives.

        1. TheOP*

          Yes, first of all, I already don’t really like the people at his work aside for a few exception. They seem like frats to me. (most of them are like straight out of college young). I actively avoid them even, which is why I am pretty against this. His trainee is a nice girl, but I just have no intention of being close with any of his coworkers PERIOD.

          1. anonanonanon*

            If he can’t pick up on you actively avoiding them, then I think you need to have a serious, straightforward conversation with him about how you don’t want to be close to his coworkers.

            1. TheOP*

              He already knows I try to avoid them. He is still trying to make an effort to get me to “come out of my shell”

              1. ToxicNudibranch*

                You know your relationship best, but there’s a difference between saying “I have these wonderful people I’d like you to meet; I hope you get on!” and making consistent requests to get you, a person he presumably cares about, to engage with people you don’t like and have no reason to regularly interact with, and labling you as somehow defective (“needing to come out of your shell”) when you reasonably decide you don’t actually want to interact with these people.

              2. Myrin*

                What on earth? People “in a shell”, so to speak, generally want to have a relationship with [whoever] but are too shy to do so. Wanting to avoid someone because you dislike them is, like, the total opposite.
                (I’m sorry, OP, from your letter and your comments I’m quite sure you know this. I just… I can’t really fathom this, to be honest.)

                1. Adonday Veeah*

                  And some people “in a shell” are happy as hell being there (I call it living large in Adondayville) and have no interest in being more social. OP, if this is you, you need to pass that message along to your BF.

                  If you truly appreciate his attempts to pry you loose from your shell, then do him a favor and guide him to do it in ways that work for you.

              3. The Expendable Redshirt*

                I got a serious *eye squint of irritation* when reading that he wants you to come out of your shell.

                It doesn’t sound like you need to get out of your shell. Oh no! You’re just not interested in socially interacting with people that you don’t particularly get along with. This is normal.

                Plus that shell phrase is maddening to me. As a strongly aligned introvert, I only have so much “I want to hang out with other people” energy. Too much social interaction, and I feel very tired. I like the human species in general, but I do chose the people I inteact with carefully. My human interaction energy is precious. The OPs boyfriend should just stop using that statement! End rant.

              4. Bunny*

                Oh man, that right there would be the start of a whole other conversation between him and me if my other half said that to me.

                I think your lad needs to have it explained to him that, when you tell him you don’t want to do a thing, don’t like doing a thing, or aren’t interested in a thing….

                It means you don’t want to do the thing and he should stop asking you to do the thing.

                Because you are actually a competent adult and do actually know your own mind. You’re not some shy little girl who doesn’t know her own needs.

          2. TheVet*

            Is it possible he’s looking for a mentor for her because of the “frat” environment and doesn’t know any other women to ask?

      7. mskyle*

        Oof, that is not a dynamic I would be cool with in my relationship – I am supportive of my boyfriend’s job (and he is supportive of mine), but if he told me he wanted me to take the “boss’s wife” role, I would have to seriously re-evaluate things.

        He’s basically asking/expecting you to do some of his work. Not cool. (And I think he’s probably doing it wrong – I don’t think what he’s asking even *is* “boss’s wife” kind of work, and if you *do* do it you’re probably going to weird his trainee out.)

      8. Jaydee*

        If he sees himself having more of a “mentor” role with his trainee, that’s fine (unless it’s really not, but that seems like more of an internal, workplace question about roles and responsibilities). But that’s on him. He should do mentor things, not you.

        Also, the whole “boss’s wife” wording combined with him “telling you” to do these things suggests that his understanding of gender roles and the workplace is perhaps a bit outdated.

        I mean, I think it’s lovely and totally normal at an after-hours work/social gathering to say something like “Oh Jane, Percival mentioned that you won the Dundie Award for ‘Whitest Sneakers’ this year. Congratulations!” But it’s usually not something you’ve been instructed to say. It’s just a thing you know about the other person that perhaps could be a topic of small talk.

      9. Colorado*

        “Boss’s wife” type of role? No, just no, no, no. I would be so incredibly offended but my husband also knows the wrath that would ensue after such a statement.

      10. amaranth16*

        First of all, bosses’ wives don’t do what he’s asking you to do, unless they’re exhibiting very bad boundaries themselves. Secondly, he’s not her boss, and you’re not his wife. Everything about this seems inappropriate to me! I don’t blame you for being uncomfortable with the role he’s trying to assign to you.

      11. Elizabeth West*

        Just because he’s training her doesn’t mean he needs to be her mentor. Mentoring doesn’t work that way. What he’s doing is part of his job, and it shouldn’t go any further than that. All he needs to do is make sure she understands the work she’s given and can function within her role without his help.

        That’s it.

      12. Bunny*

        Yeah, that’s weird. And kinda sexist and something we should really be doing away with.

        I mean, on the one hand the only time I’ve ever encountered boss’ wife-type situations is literally when meeting the wife or husband of the *literal boss of the company*, as in the CEO, and that’s pretty much always been in cases where the boss was pretty much the original founder of the company as well.

        But also because you’re actually not “the boss’ wife”. You’re not even “the trainer’s girlfriend”. You’re “The OP; teapot painter”. You’ve got your own career and responsibilities. You don’t need to be doing part of his job for him with his trainee *on top of* your own work. Does your boyfriend try to get involved with your coworkers the way he’s asking you to get involved with his?

        That emotional mentorship aspect of things? Either it is his job as trainer, in which case he should be doing it, or if mentorship outside of the trainer-trainee relationship is part of the way his employer runs things, it should be *someone else who works at that company*. Because surely the point of a mentor isn’t just to be a friendly fluffy cheerleader – it’s supposed to be someone who teaches the employee the things about working there that aren’t covered by official training, such as office culture and things to look out for, and helping them integrate into the team. How can you possibly provide that as someone who doesn’t even work there?

    2. James M*

      Or the trainee is a flirt and OP’s BF is uncomfortable about it and wants OP in the picture to put a damper on that behavior.

      1. A Dispatcher*

        Meh, if the trainee is flirty, and stayed flirty after the mention of a girlfriend/meeting her at these get togethers, the further ingratiating the girlfriend isn’t going to help anyway. Either she’s one of those people who doesn’t realize she’s flirty or she actively likes the competition aspect. It would be on the boyfriend to shut it down (as it would be with unwanted flirting even if he didn’t have an SO).

      2. Adonday Veeah*

        I had that same thought above (before I read your input). But he sounds like he’s young and inexperienced, so may not have the skills to shut this down.

    3. Erin*

      I figured someone would ask this question, but I really didn’t pick up on that. I don’t think that’s what’s happening.

  9. Sam*

    Maybe the boyfriend is already uncomfortable with his job as a trainee to a young woman, and is trying to bring his girlfriend in for that reason?

    I’m not suggesting he is attracted to the trainee or anything, but maybe he’s in an uncomfortable position feeling like his needs to integrate another woman into the group and he is hoping his girlfriend taking a role makes it seem less weird.

    1. Kelly*

      Yeah, and I’m kind of wondering if the new trainee is the only woman in the office? If that’s the case this could be a sort of misguided attempt at finding her a female “role model” somewhere within the social group they’ve built around their workplace.

      No matter what the case though it’s really not up to him who you extend your friendship to, LW, and he needs to respect your boundaries.

      1. TheOP*

        No, there’s another girl there. But it the ratio of males do dominant the number of women there.

        1. Marketing Girl*

          I am in an office (and company) with mostly men. I can tell you if my co-worker/trainer had his girlfriend/wife randomly email me on accomplishments (or anything really) I’d be like…”Umm…whaaaa?” It would not be a comfortable feeling. Even if your boyfriend has great intentions, which I’m sure he does, this is not a good idea. Being one of the few females there is not unnoticed by her, so this will seem awkward for sure. There are other great ways to congratulate someone on accomplishments than to have an outside party chime in.

          1. Chalupa Batman*

            Yes. To me, this would feel painfully patronizing. It would almost feel like I needed special coddling because he didn’t think I could integrate into the office without a “woman’s touch,” which begs the question of whether I could integrate into an office like that at all.

  10. Snarkus Aurelius*

    This reminds me of The Office.  Whenever an employee had an outside event, the only people who ever showed up were people from Dunder Mifflin.  I’m sure it was supposed to be cutesy and sweet, but it always creeped me out.

    That said, does trainee even -want- a “big sister” type in the first place?  Did anyone ask her?  I can see a big disaster if she didn’t.  She may also wonder why her employer thinks she needs so much help to the point of recruiting an outside person to do it.  

    I remember how miffed I was when my former boss tried to act like my mom; I would hate this even more.

    I also wonder what your boyfriend’s relationship with his real family is like.  I’d gather that it most likely doesn’t measure up to his ideal.  I’ve often found that when people treat coworkers like family (and in my world we are certainly NOT) it’s because they are lacking companionship in other areas of their life.

    1. anonanonanon*

      This reminds me of The Office. Whenever an employee had an outside event, the only people who ever showed up were people from Dunder Mifflin. I’m sure it was supposed to be cutesy and sweet, but it always creeped me out.

      This always bothers me because it happens SO often on TV shows. I know it probably has something to do with budget and screen time for peripheral characters, but it always seems a little weird. One of the things I appreciated about Parks and Rec was that while the focus was on the office and the characters’ interactions as coworkers, they all still had people they interacted with that weren’t involved in the Parks Department.

      1. Career Counselorette*

        I remember one specific episode of The Office where Jim throws a party at his house and his roommate is there, and Dwight actually says to the roommate, “What are you doing here? You don’t work at our office.”

        1. Snarkus Aurelius*

          A similar thing happened on Friends. Someone knocked on the door, and Phoebe says, “Who else could that be? We’re all here.”

    2. TootsNYC*

      I remember how miffed I was when my former boss tried to act like my mom

      I think a lot of people don’t have a non-family, non-friend paradigm to tap into.

      So a boss tries to “discipline” a subordinate using parenting tactics.
      Employees expect their manager to take care of them the way their mom did.

      And the OP’s fiancé is acting like a best friend/big brother sort of thing. If the trainee were his little sister, then encouraging his fiancee to nurture a friendship with her would be more understandable.

      But she’s not.

      And trying to get you to “come out of your shell”? It’s not a shell; it’s a sensible boundary.
      It’s not actually a requirement to actively seek out friendships with everyone you know.

      1. MashaKasha*

        And trying to get you to “come out of your shell”? It’s not a shell; it’s a sensible boundary.
        It’s not actually a requirement to actively seek out friendships with everyone you know.

        Yes, this!
        Come out of what shell? There is no shell.

    3. Hermione*

      I remember how miffed I was when my former boss tried to act like my mom; I would hate this even more.

      Definitely imagined a big, burly, hairy, mustachioed man wearing an apron holding the back of his hand to your forehead and ‘tut-tutting.” :D

    4. themmases*

      I also wondered about the boyfriend’s family. For some reason this letter really reminded me of an ex who had moved around a lot as a kid but had stayed in good touch with a specific friend group from several moves ago. He used to insist that after he graduated he would move back to that area specifically to be around them. I couldn’t convince him that that was a lot to put on a few friendships, saying he could make new friends wasn’t a dig at existing relationships, and these friends might have lives of their own that didn’t include staying in their hometown forever.

  11. INTP*

    I’m curious how the trainee feels about this situation, too. Imagine receiving a phone call from your coworker’s girlfriend congratulating you on some minor work achievements, and you have to pretend to be flattered and interested in this stranger’s mentorship just to avoid offending the person responsible for training you! (I know he’s not the manager, but it’s a similar situation, where he has the power to be retaliatory and claim she isn’t learning the job well or whatever.)

    I’m also wondering if the coworkers are so into being a family that they are bothered by the fact that the OP doesn’t seem interested in being a part of it, and this is the SO’s way of trying to avoid conflict instead of dealing with the fact that his coworkers might not approve of every aspect of his life. As a compartmentalizer, the SO’s request is so foreign and bizarre to me, but I figure there’s some reason that it makes sense in his head.

    1. Stranger than fiction*

      I’m noticing a lot of repeat and intertwining themes lately. Maybe it’s a summer thing?

  12. The IT Manager*

    This whole letter weirds me out. I would hate to be either the proposed big sister or little sister. I feel like the BF is maybe trying to ask his GF to participate in the training of his trainee but asking in a very weird way. And it is weird to get someone from outside the office to help train someone. It sounds like he’s going for an outside the office mentor relationship, but those have to develop naturally and can’t be forced and of course both the mentor and the mentee need to want it and hot have it be forced externally.

    1. TheOP*

      Yes, he is pushing for an outside the office relationship, something that I am also not comfortable with when it’s forced.

      1. E*

        Then tell him this, and I’m sure you can also add that it would be uncomfortable for the trainee as well. Small close-knit office or not, he needs to learn appropriate work boundaries.

        1. Ms Information*

          +1 ! And they all sound really young. OP’s “frat” comment is telling. There’s a way to have warm, sincere work relationships without mistaking them for family or friend relationships. A lot of grown up mentoring needed in this office!

      2. gsa*


        How are y’all otherwise, if I may ask?

        Other than this incident, has he pushed anything toward you before?

        If yes, this is definitely time to have a talk. This talk is about you two.

        If no, it is still time to talk. This talk is more about how he can train his person and bring her into his work family without making you a part of it. With my spouse we talk about our work and how to handle certain situations when asked, and how we handled some when it was good/bad/ugly…

        Not sure if I was on a soap box, but those are my thoughts.

        Good Luck!

          1. Rana*

            I was thinking this too. At the best, he is naive and has terrible judgement. At worst… his inability to understand appropriate boundaries and his gaslighting of the OP for wanting him to respect hers are worrying.

  13. Amber Rose*

    Kinda reminds me of when husband was really big on me befriending his ex girlfriend. It’s great that they’re still good friends, but the only thing she and I had in common was him, which is just awkward.

    I call a variant of the Geek Fallacies on this one: I’m betting that your boyfriend believes you should be close to people he is close with, in this case, coworkers.

    Time to have A Talk about boundaries. Key phrase: “I’m not interested in being her friend or mentor.” Repeat as necessary no matter how many “but she’s a nice girl” or “you have so much in common” or “give it a chance” protests you receive.

  14. Jane the Teapot*

    OP: FWIW, I had a very similar situation with my EX-husband. Within the year, he had trainee pregnant. The affair had the full support of his tight-knit group of colleagues. Adults who convince another adult they need a “big sister” type are either emotionally impaired or highly manipulative.

      1. Ms Information*

        I agree and I think it’s because drawing the OP in gives the green light to talking about the trainee outside of work, i.e. much more than appropriate for a work relationship. To give the benefit of the doubt, the boyfriend may not realize this is what he’s doing but it’s pretty typical of having a crush – or more. The crusher can’t help but try to bring the crushee into all aspects of his life. “I have to tell you all about the trainee’s personality/day/life so you’ll be able to follow up with her.” The proposal is weird but the pressure on the OP is even weirder.

        1. Jane the Teapot*

          Actually it’s so textbook behavior of someone having an affair that it borders on Lifetime TV cliche.

    1. MashaKasha*

      Oh wow, sorry :(

      The only boss who actively tried to “mentor” me very quickly ended up propositioning me as well. Might be an exception, but why why why would anyone feel the need to overly mentor another adult that’s not their child or younger sibling?

      1. Jane the Teapot*

        Ha, thank you Masha. But the joke is on those two and the “friends” they got custody of in the divorce – I’ve been happily remarried for the better part of a decade and have beautiful children of my own. And since my then-boss was so judge mental of me for getting a divorce: I got a better paying job at a cooler company. FTW. :)

        1. jamlady*

          I’m so happy things turned out okay! But everyone from your previous situation needs a punch in the face.

  15. Career Counselorette*

    I hate to be crass, but does anyone else suspect that the boyfriend is grooming both of them for a threeway?

    That’s the only thing I can think of.

    1. gsa*


      BF: I got you 3-way for your birthday.

      OP: Sweet, who did you invite?

      BF wants to invite Jill, and OP wants to invite Jack.

      Regardless, OP and BF need to talk, like…


  16. Hermione*

    Also, I find it incredibly weird that these people hang out several times a month. That’s a lot of outside interaction with a group of people you see 5 days a week, 7-8 hours a day. Does the trainee feel any pressure to attend all these get-togethers? I know he’s not her boss, but in a frat-like environment with him as her trainee, I wonder if she feels obligated to attend – and if she’s uncomfortable with the entire situation overall.

    1. Snarkus Aurelius*

      The Office Mom at my old job always wanted to do stuff like this: baseball games, dinners on Saturday night, day trips, etc.  I found it super frustrating because I -already- spent 8+ hours a day with these people in a high stress environment.  I didn’t want to spend more.

      God forbid you beg off on these things. “Is everything okay?  What’s wrong?  Do you need to talk?”

      After leaving that job, I realized that Office Mom literally had not much else going on in her life except for exercise classes.  Yes, it’s great she felt so comfortable around us, but I didn’t sign up for anything beyond the job I was expected to do.

      Be grateful I show up to anything outside of 9-5 weekday hours because it’s a gift.

    2. Jane the Teapot*

      That’s how insular industries keep control of their employees – isolate them from The Others.

    3. some1*

      My best friend worked for a non-profit like this — everyone hung out together (and other stuff together) all the time. Besides the obvious boundary-crossing, when the friendships get sour, people can very easily lose their jobs. It’s just a really bad idea.

    4. Elsajeni*

      I’m wondering if these people are all young (kind of sounds like it to me), maybe quite recent grads, maybe some/all of them are new to the city where this job is — I feel like this kind of workplace closeness would make sense for a group of people who are close in age, have broadly similar personality types, and haven’t really had the opportunity to make friends outside of work in their new city/since separating from their college social circle. If that’s the case, it also makes a little more sense to me that the boyfriend would try to help his trainee make friends. By which I mean, I can sympathize with his motivations for his bad workplace and relationship behavior — but he’s still behaving badly and should knock it off.

  17. Erin*

    I love how relationship questions inevitably bleed into the work questions. We really are blending our work and personal lives more and more.

    That being said, you are clearly in the right here. You have no obligation to take this woman under your wing.

    This situation is rather confusing, and like another commenter asked, what is his real motivation here?

    I literally am wracking my brain and can’t come up with something. Maybe you and she have something in common that makes him think you’ll hit it off, or he has a soft spot for her because of problems she’s having in her personal life or…? These seem like a stretch though.

    I would say something like, “Dale, I like Sonia and enjoy seeing her when we hang out with your work family. But I don’t work there and I’m not a part of that family, which is how I prefer it. I hope you know at this point that I feel strongly about separating my work and personal life, and I hope you can respect that, as I respect your closeness with your work family. If you have a specific question on how to provide guidance to Sonia on something, ask me and I’ll give you my thoughts. But I’m really uncomfortable with taking any more of an active role than that.”

    1. Ms Information*

      This is really good. OP knows her relationship best and holding her entirely normal boundaries will tell her more.

    2. TootsNYC*

      We really are blending our work and personal lives more and more.

      I think we always have.

      If anything is happening “more and more,” it’s that we’re hearing more stories, because we communicate so much more widely in the Internet age.

  18. Sarah*

    Does he push boundaries in other ways that make you feel uncomfortable? This whole situation is really inappropriate. Your instincts are spot on.

    1. some1*

      This is my question, too. And I’d advise the LW to really think about that, even if she doesn’t feel comfortable discussing it here. I dated a guy who crossed boundaries in “good” ways (like spending more than we agreed to on a valentine’s present), so I didn’t hear the alarm bells until it was too late.

  19. NYC Redhead*

    I agree this is super weird and I second the thought that employees are pressured to socialize with each other outside of work.
    I read the letter as trsinee needing a “Big Sister,” the program where disadvantaged youth are paired with older mentors to learn life and career skills. This creeps me out even more- to think that BF thinks trainee needs help professionally comporting herself.

  20. Jane the Teapot*

    He’s banging the trainee and assuaging his facade consience by forcing a friendship.

    1. Ask a Manager* Post author

      Y’all, this is a real person in a real relationship with someone she loves. I don’t think it’s useful to post stuff like this (and it’s certainly not conducive to making the OP receptive to the advice here). If you genuinely think that, there’s a sensitive, kind way to say it, but I really don’t think there’s anything in the letter that makes this the most likely of all the possibilities.

      1. Jane the Teapot*

        With all due respect, as someone who has been in counseling following my ex-spouse impregnating his “trainee” in an oddly similar situation: there ARE a lot of “cheater” red flags here.
        Also, just because she loves him, doesn’t guarantee he’s loyal.
        It gives me no pleasure to say this, but it needs to be said: cheaters risk your heart AND your health.
        OP, your gut knows.

        1. Ask a Manager* Post author

          But as I said above, if you genuinely believe that, there’s a kinder and more sensitive way to say it than the comment above, and that’s what I’m requesting here.

          1. Jane the Teapot*

            Ok. I had explained my own backstory above. But will be more gentle next time.

            I don’t know these people. But I do know This dude is exhibiting textbook cheater/manipulator behavior.

            1. JB (not in Houston)*

              It’s also textbook “not really understanding of boundaries” behavior. We just don’t know enough to jump to that conclusion, and certainly not definitively. I have known quite a few guys over the years who would do this kind of thing, not because there was anything going on, but because they wanted to be supportive of a female coworker but without appearing to be creepy or hitting on her. They didn’t get that the best way to not be creepy isn’t to enlist your girlfriend’s help, it’s to just not be creepy.

              1. Another Thought*

                OP, you know your relationship best. While it is important to acknowledge the advice here (especially since it was solicited by writing to Allison) it is also important to remember that many people will be affected by their own experiences when reading yours and see your situation through their own, unique lens. It is important to consider the opinion/advice of others but at the end of the day, you know your situation best.

              2. jamlady*

                My husband is a nice guy and, when he was in his early 20s, I could totally see him doing something like what your bf is doing because he had a pretty poor understanding of professional boundaries. He’d never do this now at 27, but he’s grown up a lot since we were babies haha. I would have never thought of the cheating stuff others are suggesting – you know your relationship, and if you don’t think that’s the issue, then it’s probably not. Just have a chat with him! :)

            2. A Bug!*

              What’s baffling to me is that you felt the need to even make that comment after you’d already made your point, quite successfully and without rudeness or hostility.

            3. TheOP*

              One thing, as a person who has been cheated on before, believe me when I say that I am on my highest guard when it comes to my relationships. That thought did cross my mind for sure, but right now, (hopefully not to jinx anything), it isn’t the case. Let’s just say, in the nicest way, she’s… not his type to the least. I really think he is going on some managerial ego trip where he thinks he needs to play such a huge role to make sure of his trainee’s success. He is definitely going overboard in my opinion, which is why I want to get everyone else’s thoughts.

              1. MashaKasha*

                Oh I see. Thanks for clarifying. Yes, 29 is still pretty young and this being his first trainee ever, he probably doesn’t have a clear idea of how this training thing works. Feel free to tell him everyone else thinks it’s bizarre and awkward, and probably counterproductive to the training process.

                Don’t know about anyone else, but I spent my drive home from work last night imagining myself with either my current bf and each of my exes in this situation. It’s honestly hilarious. Especially when I tried to visualize how I would’ve done this when I was with my college-professor ex – me sending emails to people’s college accounts: “Wow Tina, great job on your tenure! You go girl!” and then imagining Tina’s reaction. Comedy gold. LOL nope, it’s just not done. Tell him I said that.

              2. Ms Information*

                I know his workplace seems OK with this (is it really?) but in my organization this type of scheme would result in your boyfriend being written up with a very black mark against his professional judgement. So really not the way to get ahead! Whew, if the trainee were unionized, as many in our place are, I could also see a big old grievance being filed. “My colleague is talking about my work at home and now his SO is contacting me”. Yikes.

  21. AnnieNonymous*

    It sounds to me like the OP’s boyfriend spends a lot of time with his coworkers and is trying to come up with ways to get the OP involved in this crowd so he can double down on his social obligations. It’s possible that the trainee is the only female coworker who’s close to the OP’s age and that this scheme is an overly complicated way of trying to sell this as a fun social group.

    Anyone who’s ever dated a bartender/server and ended up spending way too much time at that bar/restaurant (while your SO never visited you at work and gradually chipped away at hanging-out time that wasn’t at his/her place of work) can tell you that this is an annoying set-up. It doesn’t sound like OP’s boyfriend is a bartender, but the whole scenario is familiar enough.

    1. MashaKasha*

      Right? What about OP’s friends, does she even have any time left for them between all the weekend and evening get-togethers with her BF’s coworkers? I’ve been in this situation too, where I had to ditch my friends to spend all my free time with his (who were also his colleagues). After he left (taking his friends with him), I realized that so had my friends, because they’d gotten tired of being blown off for my bf’s crowd. I’m a firm believer of both people in a relationship having a life outside of each other. And I’m definitely not in favor of a situation when one person gets to keep their social life exactly the way it was, and the other one gets sucked into their partner’s orbit.

  22. Mango*

    Sooo…..I’m sorry OP but the reality is that your boyfriend doesn’t understand boundaries OR he does and is not interested in adhering to them. When I read this, I sort of read it is using you as a ruse so that he himself can pass boundaries (i.e., harassment) or even use you to get dirt or gossip from a female employee who might feel more comfortable gossiping with you than him. Either way—for your end–I think you should stay out of this…and also red flag these traits of your boyfriend.

    1. TheOP*

      It’s ok, from a stranger’s standpoint the title and content will make me automatically think cheating too.

  23. CocoBeans*

    I had a (somewhat) similar situation earlier this year. My husband started a new job, and one of his female coworkers started really aggressively pursuing his friendship. This made him uncomfortable, but since it was a brand new job, he wasn’t really sure how to handle it. His solution was to bring me to a party that she threw for a bunch of people on their team. She seemed nice enough, but we didn’t really click. After the party, her focus shifted from him to me. She was emailing me fairly regularly inviting me to different things, chatting me up on facebook and gchat, just really trying to develop this close friendship very rapidly. I fended her off as politely as I could, but then she’d circle back to my husband and try to get him to make plans for us all to hang out. It was awkward for him to keep putting her off, and he was starting to find her kind of creepy too, but again, he didn’t want to make waves at a new job, so he’d sometimes accept her invitations – on behalf of both of us. (He never socialized with her alone and didn’t want to.) I basically put my foot down after one of these events and told him “Look, I’m your wife, but that has nothing to do with your work. You are not Don Draper, and I’m not smiling or dressing up or attending parties or doing anything I don’t want to do for the sake of your job. I have my own job to worry about. I’m not going to these events anymore unless someone plans something genuinely fun and I want to go, I am not responding to messages from this woman. You can go to this stuff alone if you want to, I don’t care. But don’t involve me.” After I did that, she found a new BFF victim at work, and my husband hasn’t tried to cajole me into another “Fun With Coworkers!!!!” event since. I know your situation is different, as he wants you to take on this role and is the one pushing for it, but my advice would be to really just push back, put your foot down, and say “No, this is not even remotely okay.”

    1. Lily in NYC*

      Interesting, I was wondering if the situation was something like you describe. Good for you for pushing back.

    2. NickelandDime*

      I know it was a new job and your husband didn’t want to make waves, but he was well within his right to shut down a woman pursuing an inappropriate relationship with him. When people are acting out of pocket, they lose the right to be offended when someone doesn’t want to play their games and make it explicitly clear. She was creating the uncomfortable situation, not him. Then she tried to use you to get access to him. Unbelievable.

      1. CocoBeans*

        It was one of those “boiling frog” situations. When he first mentioned her, I encouraged him to be friendly – she was married, I didn’t see her as a threat, and there aren’t that many women in that particular department. So I said “Hey, she’s lonely at work and could use a buddy, don’t assume she has designs on you!” But then she got very clingy, very quickly. She eventually left the company, and after she left it came out that a lot of people in that department had similar experiences with her, and she was taken to HR a couple of times for “boundary issues” and possibly sexual harassment. Glad she’s moved on, though I fear for her new coworkers…

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