Originally Posted by
truck
Honestly, the more root problem I sense here is that he's an introvert who feels uncomfortable in a society that mostly values extroversion. I also sense that if he were to show somebody who he was, he would feel like he would get punched in the face for it, so that just makes him hide more. While some shyness and seclusion is a natural part of somebody's personality, it sounds like maybe it's making him feel depressed and lonely.
I would try to raise his self confidence level as a friend by just encouraging him to hang around people and feel comfortable with them until possibly he does find somebody he clicks with. It's a sad cold cruel world out there, sometimes the kindest and best people do not find anybody they really get along with and sometimes the hugest assholes always get what they want. It really does blow but... even if he doesn't find a mate , encourage him to build his confidence more by learning how to get outside of himself, and even if he gets a slushee thrown on his face for the times that he comes out of the closet so to speak , well - he will learn who to trust and who not to more slowly over time.
A bit of background here: I remember when I went on my first date. I was like 22 or 23 years old about. I was scared to death. But my fear of being lonely and empty was overriding my fear to interact with people and just TRY to form a connection. I'm glad that I forced myself to give the person a chance, because it was a good relationship over-all even if it didn't work out in the end. I wouldn't overanalyze things to death here, he just seems to be struggling extra hard because his poor brain is very introverted - which is something I empathisize strongly with.