I have replied I hope you got it.
I have tried the first three ideas and he is so insular he is not willing to talk to any one. The third has occured to me but he is adopted from 6 weeks of age and I know feels that one woman has deserted him so I don't feel that I can do the same. Whe he was at one of his 5 schools (privately) he saw a lady who was in your field but she got no where with him and he finished up doing his GCSEs from home before he left education for good.
I do appreciate your advice and no this is not an easy one!!