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?


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.
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.