Helping professionals, how do you keep yourself from sticking around situations that aren’t healthy, but the person needs help (without feeling guilty as hell)?

I’m a social worker and my empathy levels are… sometimes unnaturally high. I feel for people, I have a big heart, I always have. Even as a little girl in elementary school, I spent more recesses sitting with the kid crying in the corner than I ever did playing.

I’m divorced after having spent my twenties in a good marriage where our goals just stopped lining up anymore, and I’m having one hell of a time trying to date again. I recognize the helper in me starts talking to people in an attempt to date, and the naturally empathetic and warm person I am allows people to open up really easily. Unfortunately, this has been winding up with me getting a lap full of baggage and then feeling guilty as heck when I want to bounce.

More specifically, I met a guy who I really enjoyed and clicked with, everything was going really great, and then it was like a tidal wave of depression, anxiety, and self-degradation hit him. I really connected with this person, and so it breaks my heart to see what he’s going through, but his anxiety and self-worth issues are putting up a lot of walls for me to even try and support him through this. I’ve tried to offer my help and support and it’s been point-blank rejected. Which is fine, but every time I try to stop talking to him, I am consumed with guilt.

So, how do my other helping professionals keep your worker heart and your dating heart separate? How do you walk away from “toxic” (I hate that term but can’t think of how else to phrase it) dating situations without being consumed with guilt?