Have you ever considered therapy?
Can't speak for Indy, but as someone with many of the same issues, there is no way I could even consider just showing up somewhere and talking to a stranger. My campus has free services yet that somehow makes it even worse.
I tried therapy for a couple weeks and, while it was somewhat comforting, I didn't feel it improve my situation.
I've seen psychiatrists and counselors before. At one point in college, I joined a support group for people with social anxiety disorder only to have the therapist leading it basically tell me he didn't think I really had SAD because I did fine during the cognitive behavioral exercises. I even broached the possibility that I might have Asperger's or otherwise be on "the spectrum" but was told I didn't meet any of the diagnostic criteria.
On some deeper level, I think I have trouble trusting people and I do have a very deep-seated fear of rejection. I've never had any close friends and acquaintances never become anything more. I don't seek out friends because I don't want to be in a situation where someone doesn't like me. The pattern always repeated itself when I was growing up. I'd meet someone, whether it was through a class or some activity, maybe they'd ask me to hang out once or twice, and then they wouldn't. I'd never ask them and certainly would never actually strike up a conversation with a stranger. But now that I'm older, people don't really seek out friends the way they do pre-adulthood, so those situations never come up. There are literally maybe five people who I'd even consider asking to go see a movie or something and they all live in other parts of the country. I don't really know what it's like to be mad at someone or have a serious argument or disagreement with them, because I've never been close enough to someone to be anything more than cordial, courteous and distant.
The only dates I've ever been on were ones where the girl more or less asked me out. And I never took it any further, because, again, I don't want to be rejected.
I work at a job that I'm probably overqualified to do - in part because it was virtually a given that I was going to be hired and because the work is so mundane and unchallenging, I basically can't fail. Even sending out job applications is hard for me because I don't want to be rejected.
Basically, I've led an extremely confined, risk-averse life and have found, sadly and perhaps too late, that there aren't any rewards to that kind of life. There's really not anything at all. To paraphrase one of those schlocky motivational posters I used to see in school, I've never taken any shots in life, so by default I've missed them all.
There's not really a convenient diagnostic box that I can be put in. I've taken antidepressants for years. They don't make me happy, but they keep me from feeling too sad. I'm sad right now, but it's nowhere near as bad as about a year and a half ago when I didn't get out of bed or eat for a week and contemplated suicide and was literally crying (something I'm not sure I'd done since I was little).
