resolved

- In my opinion, it sounds like he's lonely, ya know? I know many guys who claim they are going to turn into the "asshole" because that's supposedly all girls really want. Contrary, many of us don't know the guy is a jerk on the inside until after months has passed. It seems as if he wants to start a relationship, after all you said he hasn't had a girlfriend. Sometimes you have to be blunt with someone in order for them to learn, like me for example. I'd actually ask him if you could be full out blunt with him, as a warning as to what you're going to say is going to be harsh.

resolved

- Suggest a therapist? It seems as if he does need some help maybe sorting out his life.