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?


So John doesn’t like his job. He also seems to be not performing well. He is vocal about it to the point that it affects others. Are you, as his manager, addressing this issue?
Yes, I was actually addressing it before he told me about his desire for Jane. I try to be friendly and on good terms with all those under me, but I am not friends with them to avoid bias. He just tends to over share a lot.
From a business perspective, I am trying to ensure my team member is performing as best he can.
From a personal perspective, I am actively trying to not have this guy kill himself from pushing too hard. He can’t afford to be fired, he has made that well known. Before you ask, I don’t make pay decisions. He stays because he has to. I and my staff have tolerated some of the complaining, but I will talk to him when he starts going overboard. He is a good guy otherwise.
Do you do the proper business action or do you do the right thing? I am not heartless.
That’s tough, and I hope you can manage it in such a way that it is not a huge detriment to the team. I hope you can also share this burden with your manager because that is a lot.
About the dating situation, I see a lot of downside (potential for messy drama, meltdown of an already vulnerable direct report, HR issues if things go wrong) and just a little upside. I’d keep it professional, and if you like her enough, I’d wait until one of you leaves for another job, and then get her number to keep in touch.
He may move to another shift at another building if he gets a new position he has applied for, so it may resolve itself. Although I can’t be sure of any of that.