

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.






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.