A guy I've known since elementary school, who's become increasingly antifeminist, just asked me if he could talk to me, because he has no one else. The last time we interacted, he hijacked the comments on an article about feminism to complain about how male privilege isn't a thing and how he gets rejected (shocker) from feminist spaces when he tries to go in and complain about men's issues. I tried to educate him, and it didn't work.

The time before that was a similar interaction. He still complains about how I was "hostile" to him. Previous to that, our interactions consisted of him talking about his problems with his girlfriend, his drug use, his depression, etc. broken up by occasional letters announcing that he was still in love with me.

Prior to THAT, he refused to speak to me for two years because I was dating someone else. Also, once he went to Homecoming with a friend and I, and pretty much ignored all of my physical boundaries while we were there, despite my moving his hand off my back, stepping away from him while dancing, actually leaving the dance, and later removing his hand from my hair. That was a long time ago, but still, not indicative of health in our relationship.

I don't know what to say. I know I can't take care of his emotional needs anymore, that bullshit is over. But I don't want to make him feel more isolated or push him into a darker place. Any suggestions on how to make it clear that I can't take care of his feelings like I've tried to in the past while not hurting him or making him feel completely alone when he's in a vulnerable place? Apart from anything else, I'm not myself in the strongest state, and while I'm doing pretty good I know I can't take on anyone else's problems right now—especially someone who at one time told me I was the only thing keeping him from committing suicide when he knew I was in the middle of my first struggle with anxiety. SIGH.

Any experience with issues like this, or advice?

ETA: I messaged him with this: "I'm sorry, but I'm not in the best place myself right now. I've gone down that road before and I can't do it again, emotionally. I don't know if you are seeing anyone professional, but I think that's a better option."

And he said, "Okay."

So that's...something. I feel a liiiiiittle but like this:

I don't know what to do, guys. Update!

And also the mean part of me that says:

I don't know what to do, guys. Update!S

(I just figured out how gifs work in Kinja right this second, if you can't tell, which has significantly cheered me up).

Thanks so much for all your help, guys!

I don't know what to do, guys. Update!S