I had a landlord once who wasn't very social, and as a result wasn't very good with women (but he was a specialized mechanic and made a ton of money). Was talking to him one day, and he said that his therapist had given him an assignment to get out of his shell.

His assignment was to go to a bar (or any sort of similar place) and get rejected by ten women. That is, between that session and his next (the span of a week I believe), his goal was to get shot down by ten women in a social situation. Not necessarily crash and burn, but some kind of rejection.

After a while, you realize rejection isn't really that bad - it's the fear of rejection that's the big problem. Once you can get over that, you're going to be doing a lot better.