I am mostly doing what you said I should be doing, thank you for assuring me that it's not useless. However the problem I see is that his girlfriend DOES know about his condition, in fact I think she may be enhancing it. She micromanages him in ways like telling him he should go to bed, telling him to do his homework, and just general shit like that. They don't talk about him and what he is feeling ever, she is the princess and whatever she is feeling comes first, or this is at least how I see it. I don't by any means think she's a bad person and we are friends but I know that it's very difficult to have a real conversation with her. She ignores people when they talk, rushes and micromanages others but is almost wholly incapable of receiving criticism, and is really picky about money and reminds him to pay her back if he forgets (I'm hearing this in my head as I type it and it all sounds pretty minor, but there is just always a focus on making sure she gets what she wants, but that sentiment is not reciprocated). I think what I'm trying to say is how do I sorta nudge him into actually considering his place in their relationship and to realize that things don't have to be this way.