Should i stay or should i go?

so, i met this guy about two weeks ago, it turns out my dad used to be his principal, and we've become fast friends and gone out three times--fooling around a little on the last one.. he says he's not wanting a girlfriend, mainly because he's never had one, and a bunch of his friends just got out of bad relationships and he doesn't want to get into something just to have it end horribly..which i guess makes sense. problem is he's a really great guy, inside and out, and i'm not one to jump ahead of myself, but i'm thinking i could end up falling for him...but i still don't know that he'd want to do anything about it later, if ever...so do i keep it casual and see? or check out now? aah! lol