One of my best friends whom I have known since college is dangerously close to getting "nice guy" syndrome. He is 43 and has never been married. He has a really tough time with relationships. It's getting to be really painful to read his Facebook posts or have a conversation with him because he is becoming extremely bitter. On one hand I can understand his frustration. He is short, bald, and on disability due to severe Asperger's. That is a lot of strikes against him that he can't do anything about. He is also very outgoing, friendly, and loyal. If he continues down this road of bitterness, then he's going to lose those things about him that are great.
Honestly I think one of his biggest problems is that he doesn't have a very good filter when it comes to judging others' character. He can't tell when people are being insincere. He literally wants to be friends with everyone, can't tell when people are merely being polite, and gets extremely hurt when people don't return his calls and efforts to get together. I am pretty sure this is due to his Asperger's. Most of the women he winds up dating are majorly damaged goods, and he doesn't see it until it's too late.
I don't know if I should say something to him, and if so how I should say it.