Girls, I have a friend who used to be a fake 'nice guy'. He's learned to be a real one but now he hates himself (see details). What should I do?

Anonymous
I should stress that he actually is a genuinely good person. He has always been shy and cautious around girls. After I turned him down, because he'd put me on a pedestal, he found it difficult to take no for an answer. Eventually, I gave him a thorough grilling over his behaviour. He clearly took that to heart because he did accept my choice after that and gave me my space. He knew what he'd done, took full responsibility for his actions and apologised. He even tried to turn himself in for harassment, but I explained what actually happened and the police wouldn't arrest him. I wanted to repair the bridge with him after a while and he's gone back to his kind, shy self.

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?
Girls, I have a friend who used to be a fake 'nice guy'. He's learned to be a real one but now he hates himself (see details). What should I do?
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