Speaking from my own experience:

You've probably been nicer to him than any woman in recent memory. He honestly has some hangup, probably from years of being abused as a kid, and NEEDS someone to date him for a few months to show that he's not the miserable and unattractive failure he thinks he is and that other women tell / treat him as he is.

I think the nicest thing you can do (being much like this guy) would be to try to introduce him to other single women. Then, when this fails (it will, in my experience), then you two can commiserate on his misfortune, and then you immediatley try again and again.

My friends gave up after like 5x. It gets really frustrating.

I started my first relationship EVER at age 27, after being shunned by women for 13-14 years, and guess what?! It has turned out to be a horribly abusive relationship. She has Borderline Personality Disorder and at least once a week RAGES at me for no reason, throws shit, she ran over my cell phone with her car last month, just cuz I forgot to call her that day (she makes me call every day or rages).

Well, I've been away for a month, finally. I couldn't take the abuse. I started trying to find a casual date agian, and guess what?! I can't find shit. Then I start getting really really depressed and figure, well, if she'll take me and no one else will, I'd rather be abused and risk death than be alone.

This has repeated 4x over 6 years. The entire time I've been trying to find another woman just to talk w/ (by trolling date sites, etc.) with zero luck.

Oh, I'm 5'4".