L.J. Writes

He was our first experience with a guy who noted our body, but in such a way that we never felt skeeved out or afraid, because we knew we could always tell him he was full of it and he'd take it with grace and cheer.

I think that's a really important point. I've been corresponding with a teenager in Europe who recently asked me whether the only way he could avoid being a predator and a creep as a straight male was to be celibate forever. Obviously there's a dash of bratty belligerence there, but I think the question is genuine and I hurt for him. I did give him some pointers, that there's nothing wrong with finding someone attractive as long as he's polite about it and respects the other person.

Reading your anecdote, though, I think the more fundamental point is to remember that a) he is not entitled to other people's bodies, and therefore b) "no" is a valid answer. He is not diminished if a woman tells him no, it is not an affront or judgment on him by itself--and well, if she' a jerk about it, then that's on her and not him. Good thing he got to know in advance, right?

Unfortunately I think he is at a point where he sees "no" as an indictment of his self-worth, and that's what makes it so hard. Guys like your high-school friend and Thomas are the rare ones, men who are secure in themselves so that they're not driven by the social pressure that says getting women is a validation of their worth as men.