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.

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

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?

Complicated.

Is Jane your peer or beneath you in your corporate structure? What level is John compared to Jane and yourself? What are your corporate policies regarding in office partnerships/romance?

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

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.

I've done the workplace romance thing several times. Realistically as an adult this is where you are most likely to meet someone, so IMO if you approached with a little bit of caution/maturity and think Jane could do the same I would proceed and just keep it quiet.

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.

You know what my therapist would tell me in this situation? You're no hero. It's not your job to save John.

This is not complicated at all. Ask her out and let her choose. Have a polite, but not too close relationship to the guy who is basically your subordinate. If you think he might harm himself, take action, but other than that your not responsible for his wellbeing.

Also, it sounds to me that you are trying to be absolutely fair to this guy, not only in this thread but also at work, but not necessarily like him too much. I’m also pretty certain that she was just polite to him and didn’t want to upset him. Talk with your love interest, than you will know.

No idea how to deal with this. Keep us updated and good luck

Personally, I have a no dating at work rule.

Unless you and her end up marrying, there are very few potential positives here and a whole load of almost definite negatives.

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.

As a manager and somebody who enjoys being able to pay my bills, wouldn't mess with any of this. I have had subordinates take interest in developing a personal relationship with me. In some cases I share that feeling, but I still tell them as their manager it would not be appropriate to proceed due to the potential impact in the workplace. Quick way to get accused of giving special treatment and moved or terminated. Very hard to hide.

If you and Jane are in an equal level role or one of you is willing to quit or change roles, go for it.

John's personal problems sound like they are effecting his work performance. If you are his supervisor you are responsible for handling that in some way. If you let too much slide because you feel bad for him, this will go from a problem with John to a problem with you. It is John's responsibility to manage his personal life and be able to do his job within the expectations of the company. If you are sharing that the expectations aren't be met in similar ways multiple times, cut the cord.

Regarding your expectation of John taking issue with you and Jane becoming a thing, kinda depends what Jane wants if you ask me. And I'm sure it's scary how John would react being rejected but again, that's on John to deal with. I'd just be straight up about it. Sorry man she's into me and I'm Into her. That's bad news, but if he can't handle that in a mature manner that's on him. He'll end up quitting or getting terminated for an emotional outburst. It's sad, but it isn't your responsibility to control how he responds. Personal problems are personal problems. Generally, managers that are managing lower level managers understand when somebody on the team just doesn't click or behaves in a way that wasn't within your control or purview. They have been through the same shit themselves.

Ensure you are operating within the confines of your handbook/guidelines if you want to keep your job. That's the biggest thing.

Expect this to become an HR issue if John doesn't immediately quit. I would avoid moving forward with an attempt to terminate John after he identifies the you and Jane situation as that may look retaliatory. Either get HR or another manager involved to ensure John is clearly being terminated for valid reasons and that other people are involved in that decision.

If you want to go the more sinister route (some people do). Terminate John with solid documentation on the performance issues. Negative attitude possibly. Consult your handbook for options, but ultimately you can terminate him and wait on moving forward with Jane until he's gone.

If you take nothing else from this, consult the handbook. If you want to keep your job all the information is in there. You can get it from HR in the event you don't already have a copy.

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.