OP here.

>> As for him liking the other girl, I'm guessing he's quite the obsessive type

Not really, unless you count Assassin's Creed, Halo 3, and God of War. If he was a regular Anonymous, he'd be gar for all of them.

What >>3 says really depresses me, because it seems the most realistic. I don't want to give up on him, though. If I did, his self-confidence might fall even lower. I want to help him get past all of that.

I'll try backing off some more. But waiting until he asks me is really impossible, because I know that he won't. I mean, he doesn't even believe he'd get into an ordinary Community College, which is stupid, because we both currently go to one of the top high schools in the city, which is pretty huge, AND he's in the top quarter in rankings. I doubt that it even occurred to him that he might want to get out of this position.

Or I can just knock him unconscious with a calculator, tie him up, and force him to get drinks with me. How scary.