Hamurabimbi
Master Don Juan
Over the years. Several of my GFs have offered/tried to help. He seems terrified of women though, so it really hasn’t worked.You’re a good man for trying.
Have you considered talking to female friend and seeing if you can set something up for him with a friend? Like just someone that’ll agree to be talk to him and asses him from the female side? Just to get him some courage?