Tldr at the bottom.
No real names, sorry. I (28M) am a department lead at my job, Jane (25F) is also in a similar position in another department. John (~23M) is in my department working under me. I am his direct supervisor. I am on good terms with John.
A few weeks ago, Jane has been reaching out to me for casual conversation unprompted and will come get me for any work related cross department needs no matter how minor. I can clearly tell she is interested in me as nobody is that persistent with casual conversation or finding ways to interact if they weren’t. She has told me I am her favorite person to work with even though I barely know her.
Jane is cute and also hilarious, I wouldn’t mind dating her and have considered it if we end up being a good match. So far so good anyway.
Bring in my coworker John. John is an interesting character. Funny guy, good heart, openly a furry, Bisexual leans gay, and rascal like personality. John also has depression and sees a therapist. He openly hates his job even to his own coworkers dissatisfaction. We don’t deal with the best of work, but it still gets old hearing it for everyone. John is also easily distracted to the point of causing issues with his work performance.
I like john, he stresses me out at times but I try to be patient as I know he lives a rough life. He will confide in me often about his issues. Most recently he had a episode to where he got so distracted his partner was doing all the work and the partner snapped at him. I had to talk to both of them, one about his yelling even if justified and John with his lack of focus.
My discussion with John turned out alright, he hates his job and wants to leave but appreciates me. The only reason he stays he tells me is because of his interest in Jane. He has apparently asked her out before and she said she would. Don’t think they have yet. They are friends to my knowledge.
Obviously, I don’t want to touch this problem with a 10 ft pole from a job perspective. I like Jane and I am damn well certain she likes me as well from how she interacts with me and I believe that will interfere with John’s life even if I do nothing. John is a good guy that is teetering on the edge of mental stability and I have no desire to not only break his trust in his mind by going to “steal his girl” after he told me about his desire for her, but also push him over the edge.
I don’t think she is giving up either. So what should I do?
Tldr: cowork likes me, I like her, other coworker I am in charge of likes her and has gotten a yes from her when asking her out but no date yet. Coworker has depression and ended up telling me about his desire for her recently. Doing nothing is not an option as she pursues me. He persues her. Me dating her would likely cause him to meltdown. What to do?
The smart move is: don’t get your honey where you make your money.
Jane is not interested in an intimate relationship with you. She is being a polite and considerate coworker looking for support from a friendly face. Help her without turning it into more than super and teamwork, and it will eventually just turn into a deeper relationship if she really is into you. If not, then it was never going to anyway.
John is your subordinate. He is reaching out to you with trust for support in this time, but he ultimately cannot get the support he needs in his romantic/personal life from work. If the only thing keeping him there is her then he should leave, and you should support him there. Either make it a place he wants to work at outside of his (AND YOUR) romantic interests or use your professional resources to find him something that is a better fit.
You need to be very careful with both these dynamics.
What would you rather have here: someone looking to build interdepartment trust and friendship and a subordinate who wants to be at work, or a subordinate who feels like you don’t care about him and a coworker who feels like you think so highly of yourself that every girl who talks to you wants to date you?
There is no third option where you get the girl and fix the kid in the situation as you describe it.
Look, I understand your point and I shouldn’t consider any woman being nice to me as flirting… But in this particular case, she just asked me for my phone number yesterday so she could quote " get to know me better and continue the conversation over the weekend." We have odd work weeks and this is the start of our weekend.
I don’t think there is any mystery about that part anymore. I had asked if she was seeing John and she said no, they are just friends.
As for John, he was denied for the role he really wanted to apply to for very dumb reasons and I am very upset for him. There is nothing I can personally do about improving his situation as the things he hates about our company are not within my or even my superior’s control. He has told me he can’t leave either as he can’t find a job elsewhere.
I want to be supportive of John, but I am even trying to push it in this direction, its just going there on its own and I am currently not stopping it as she is an awesome person I would like to get to know better.
You are right though, there is no option where “I get the girl” and not burn bridges and not torch themental health of my coworker. Even if I said no, he will still be hurt as she is clearly not interested in him. Just to a lesser degree.
I’d seriously ask myself if he actually asked her out and she said yes, or if he’s basically trying to preemptively stop anything between you two when he noticed she likes you and guilt tripping you.
Dating coworkers is a mess even without the whole situation though. Confiding your love affairs to your boss is such a red flag though. No one does that.
Confiding your love affairs to your boss is such a red flag though. No one does that.
Disagree. One can have a “boss”, or one can have a “manager.” My entire career I’ve tried to get to know the people around me, my manager, my director, my peers, other random people - everyone I can. I spend a LOT of time with these people, and everything being “professional” 24/7 is draining. We’re all real people, with real lives, real interests, hobbies, etc. - and the happiest I’ve ever been while working is when I was surrounded by people I wouldn’t hesitate to call “friends”, and that includes discussion personal issues often - maybe not quite as much as I would with say, a friend from high school, but close.
Related - I married a ‘girl from work’ many years ago, and the person who was both our manager when we got together, and still my manager when we had the wedding, was one of my groomsmen. I did not know this man before starting that job, but spending more time with him and interacting with him more than my ‘high school friends’, by a LOT, over those four YEARS, meant we easily became at least 80% as close as I was with any of my outside-of-work friends.
Edit: And I actually just remembered, said manager met his wife at work too! They are still happily married unlike my ex and I (who are happily divorced and have the best/healthiest relationship that we’ve ever had now.)
I agree to some extent. I might be more reserved, I just can’t imagine telling anyone I work with I have a crush on a fellow coworker.
I still like joking around with them and I do have more of a manager than a boss as well. I get what you mean.
To be fair I am talking about like, 2000-2010 here lol.
Though I remember having a social outing just a couple years ago at my current job, and I remember my team mate and I’d say pretty good friend (who again, only met through work, but we clicked and connected) telling me after that he was really into this one girl that was there, and then a week or so later updating me that he’d asked her out but she wasn’t interested and he was (obviously) leaving it at that … and he’s quite young, I’d say mid-20s.
I do probably give off the “feel free to talk to me about casual and personal stuff” vibe though as I 100% loathe and reject the whole ‘corporate culture’ bs, and I currently work at the stuffiest most uptight place I’ve EVER worked at, lol.
Also tech industry, so I think we’re generally a lot more casual? No idea! :-)
That is a noteworthy thought. He doesn’t cross me as him knowing or catching her interest when we have all interacted with each other at the same time. Generally when people notice that, they start getting defensive and get somewhat possessive. He was just really happy to share the info like he was gossiping with a good friend.
Well I try to stay away from any work relations personally. It sounds like he’s innocent about it more than anything. People usually don’t share that info specifically because of situations like this. I think it’s fine to go for it if you properly like her. I’d ask her to keep it out of work and keep it as a kind of secret relationship at least for the beginning, but he’ll hate you even more for it when he does find out.
It kind of sounds like he’s got puppy dog love going on. I only know a bit about the situation but I feel like she isn’t going to jump in his arms the moment you back off or something. I definitely wouldn’t feel bad about it.
There’s other things to think about. Are you technically her boss too? That might affect the office gossip.
I am not her boss, we are at a similar level in different departments. I don’t have to interact with her at all if I didn’t want to. If I did date her, the odds of it coming out to him are high. It would just be a matter of when. He would likely notice that she didn’t follow through on their date plans.
I would definitely wait to see how their date goes I guess. Tough situation, good luck!
Question is, will there actually be one? I do not know.
Date them both, start a polycule!
Don’t date a coworker, it’ll be really awkward if it goes poorly.
What are their respective stances on the Iran conflict? Do they have a favorite Gulf monarchy?
Finally! Now someone is asking the big questions that we need answers to.
You obviously need to close the love triangle: go date John.
John and you both have mutual interest in making yourselves “hard to get”. Dating each other would make Jane jealous and only increase her interest in you both.
It would be cruel to force Jane to chose between you too. If you navigate this carefully, she can have you both and you can both have her on top of each other. Everyone can be happy. /s
It is the only reasonable decision.
There will be other Jane’s that don’t work where you work.
I know he lives a rough life.
*ruff life, ftfy, no further comment
Definitely a tough situation. I hope things work out well for all of you. I’m also extremely curious about what animal John has for his fursona.
FWIW, I’m not too worried about John’s dating life. The furry community is pretty strong and cross-functional, and there’s a ton of hobby overlap with furries and other hobbies and sports. Especially if he’s bi, there will be others that he will meet, and he’s young. Hopefully his depression gets better.
It is a Sergal and a Protogen. The fact I know without any hesitation for thought is bizarre. lol He is not a bad looking guy, so I am sure he would be fine. Doesn’t make the emotional pain sting any less though.
Nice! And yes.
To answer your title: don’t shit where you eat.
Jane sounds lovely, and based on what you’ve said, it’s unwise but not wrong to go for her. Dating a coworker is shitting where you eat, but it’s usually mild.
John seems like a good kid, but he needs a conversation about professionalism. He put you in an uncomfortable situation by telling you he’s romantically interested in a coworker who’s been hitting on you. You probably shouldn’t know he’s a furry either. Hell, you shouldn’t know he’s so unhappy he’s looking for other work. He sounds neurodivergent, and that’s cool, but non judgementally, he needs to be aware that that level of openness with coworkers can cost jobs and possibly even risk sexual harassment claims.
Like let’s remove the you and Jane leg here. A generic friend of yours is telling you that he thinks he screwed up, he told his boss that the only reason he’s still working there is because he’s trying to date the head of another department. He’s asked her out, but nothing seems to have come of it, but it’s ok, they’re friends. Somewhere in this conversation he mentions that everyone at work knows about his mental health struggles and that he’s in therapy. How fucked do you tell your friend he is? Because I’ll say this, I’d be terrified that friend is misreading the situation with the woman, she’s afraid to say no (if they were actually friends he wouldn’t need to see her at work to pursue her), and she’s afraid to turn him down directly lest he hurt himself. And barring all that, he’s still given them reasonable cause for firing. That’s not necessarily the situation or even the most likely scenario, but it’s a plausible one.
I’m sympathetic to John. At my first few jobs when I was his age I was far too open about myself and my life. I never hit on coworkers, but otherwise relatable. It fucked me hard, and I really benefited when I learned to create a professional boundary and barriers.
Also, figure out your liability in all reasonable scenarios. Not from strangers on the internet. If John’s advances on Jane are unwelcome are you going to be in trouble for knowing and not reacting.
“He put you in an uncomfortable situation by telling you he’s romantically interested in a coworker who’s been hitting on you. You probably shouldn’t know he’s a furry either.” I was aware he was a furry on his first day with me, he does not hide it whatsoever. It is an open part of his personality that I have just come to accept as it is harmless if not a bit odd. He tends to overshare things so you might be right.
He has taken a strong liking to me for reasons I don’t fully follow other than some of our interests align. I wouldn’t say I discourage it though as I have a discord channel just for our team where people also post memes and things on our off days. I am MUCH friendlier to my staff than your average boss, but I have a strict rule that I will not hang out with any of my coworkers where they cannot all be involved if they wish and I cannot show favoritism. I have only been taken up on that once. I won’t blame him for wanting to trust me with that information, I have been told I look trustworthy or something.
As far as I have seen, she and him are perfectly friendly with each other, now recently working as a team to cause harmless, minor havoc in my life for fun. lol I don’t know the full extent. I do know that they have known each other for a while too and they like to send memes to each other. I just don’t know if the romantic interest is there though. Kind of like having a good friend that is also into you but you don’t share it. I don’t know.
I should clarify, it’s not your fault you know these things, but he needs to learn that enough bosses won’t be understanding that he should learn to curate the aspects of himself that he professionally displays.
Having good and amicable professional relationships is awesome. My coworkers know that I’m into bicycles, they don’t know that the bike shop I volunteered at was explicitly anarchist. They know I’m married, they don’t know I’m polyamorous. He needs to learn to find a level of sharing that can keep him safe, because elsewhere in the thread you mention he’s on the verge of disciplinary action.
You seem to have professional boundaries as well, and I think that yours are totally reasonable. A friend of mine is a manager of software developers and she has similar boundaries to you with her subordinates (she describes her job as basically being a kindergarten teacher for adults), but if you have to discipline John, that closeness will bite back.
And it’s good that they seem to actually be on good terms with each other, though she still may have given him the old pocket veto.
Have a conversation with John, make it clear you aren’t disciplining him, but attempting to help him in his career, because this oversharing is going to fuck him hard someday if he doesn’t get it under control. It’ll be a lot easier of a pill to swallow from a boss he likes and respects than from one who brings in HR on his first week. He should know you’re doing this specifically because you think he’s a good guy and you want what’s best for your subordinates.
For what it’s worth it sounds like you quite like this lady and like nothing you do is going to avoid a mess, so yeah have fun with that. I don’t think John is going to avoid pain here. Both from what you described of that crush and from what you’ve described of him possibly needing a PIP. It sucks, and it really sucks for you. But fr, act like he didn’t tell you about Jane and pretend you forgot. It’s probably the only winning move here even if it sucks. Well, that and posting follow ups. Posting follow ups as things continue is the ultimate winning move.
“He needs to learn to find a level of sharing that can keep him safe, because elsewhere in the thread you mention he’s on the verge of disciplinary action.” Agreed, he overshares way too much and it is going to bite him on the ass at some point.
My closeness with my team is unavoidable and is better I lean into it. We work long shifts and I must interact with them constantly. Managing the children as a kindergarten teacher becomes a lot easier when they like you personally.
“But fr, act like he didn’t tell you about Jane and pretend you forgot. It’s probably the only winning move here even if it sucks.” I don’t that will fly sadly. He has mentioned it twice now.
“Posting follow ups as things continue is the ultimate winning move.” You just want to know how this nonsense plays out, don’t you? lol
What can I say, I’ve been completely honest I don’t think there’s a winning move and this sort of posts are what I miss from reddit lol
I never thought I would be in one of these types of posts either. It has gotten spicier. Out of curiosity, I had ended up asking her if there was anything going on between them to which she stated that they are just friends and he asked for her number. She does not want to lead him on according to her. Yesterday she asked for my number and I said sure.
Lady is moving this faster than I had planned for.
Damn dude, congrats! Gotta appreciate someone who’s clear about her intentions
I know, such a breath of fresh air!
Even without john Im a strict don’t shit where you eat person. If I don’t like a person enough to go work somewhere else or vice versa with them then. nope. However I also don’t really make friends at work I make aquantences. I work and head home and by and large keep it all seperate. I have likes some folks at work and could see being hang out friends but you know part of it is being older and married. I just don’t hang out like I did when I was younger.
Tbf, I see you as more of the issue than anything.
You’re a leader at work and have gotten way too involved in the personal lives of your coworker and subordinate, regardless of intent.
My advice is to look outside of work for interpersonal and romantic interests. You are already experiencing the consequences of your involvement, and the way you feel about this situation is the signal you should be listening to and taking heed of.
Like you said, I didn’t ask for this information, it was just thrusted upon me. Even if I did nothing whatsoever, the situation would have still existed with or without that knowledge. Not knowing makes it worse to be honest as now I know to not move with reckless abandon.
Looking outside isn’t always an option. Finding the type of person I like is not usually done by looking outside of work unfortunately.
Threesome!
Joking, obviously. Seriously though, on paper, I’d discuss it with her openly and honestly, say I’m interested, but it might be better if we wait until John moves on, either to a new job, or a new girl. In reality, I’d probably just do nothing, not having the courage to talk to Jane about it.
She doesn’t know that I know he asked her out, I would imagine. Would be kind of awkward to bring up as I haven’t even asked her out yet. lol
“Threesome!” Ah yes, the true answer that I was looking for. I should have seen it from the beginning. Haha
I really don’t see why this isn’t the genuinely obvious beginnings of a polyamorous relationship. It’s not the easiest thing but plenty of people do it.
Well all the pieces are there. However, for me at least, I don’t like sharing. Lol
She doesn’t know that I know he asked her out, I would imagine. Would be kind of awkward to bring up as I haven’t even asked her out yet. lol
Oooohhhh, yeah… that throws a wrench in to it. I will ponder and reply again if anything magical comes to mind (highly unlikely!)
Good luck!
No idea how to deal with this. Keep us updated and good luck
That makes two of us. lol
You know what my therapist would tell me in this situation? You’re no hero. It’s not your job to save John.
Its not my job to save John, doesn’t mean I won’t feel bad regardless. I do care even if I try not to.
I’m not saying you should be a jerk to him. Just don’t let his dreams drive yours. You can be honorable and also pursue your desires.
Edit: side note… For all you know, John told you about his romantic interests because he was jealous of how Jane was acting towards you.
