One more story, I remember I used to date a girl who seemed convinced I was seeing other people, for a night or whatever it was. Anyway she used to accuse me of stuff I wasn't doing, even when I denied it she wouldn't believe me. I remember thinking that if i'm going to get accused of stuff i'm not doing I may as well do it anyway, as i'm still going to get accused of it.

Sounds like there needs to be some more trust there. (if that's what it is at least in part about, assuming so since you say all his female pals "hit" on him).