Since then though, another friend of mine has taken interest in him. I know he likes her too, so I encourage him to go out with her, but he won't on the grounds that he "has no right to ask her out" and that he refuses to violate her boundaries like he once did to me. I keep trying to tell him that this is different because she likes him, but he denies that she does.
He seems to be convinced that no girl likes him and that even if he's wrong, he doesn't deserve to be with a girl, that he's untrustworthy. I think he's hyper worried about repeating his past mistakes.
What do you make of this? And how should I encourage him to forgive himself for a mistake that he's recognised, admitted to and apologised more times than I can count for?