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Hi again Vesper,
Out of all the women in the world, there is not one that will suit your friend. He’s playing the ‘poor little me, no-one will ever want me so I may as well resign myself to being single and live with bonsai and cats’. (Japanese men have wives.)
I’m not sure what you do with someone who is so down on themselves – he’s the one that has to want to change. Unless he recognizes that he has a problem, he won’t embark on any form of self-help or improvement. You can encourage him to face the past if you ever get to talk to him again or you can move on, meet someone who does want to be with you full time, and perhaps stay in the background for your friend who seems to want to wallow in self pity for the rest of time. From what you say, I don’t believe that a love relationship would work out between you.
Peggy