What is it that you’re afraid of?
I used to have bad social anxiety (mostly I would turn beet red whenever I was nervous or uncomfortable) and the more it happened, the more I lived in fear of it happening. I worried about what other people thought of me and that they were judging me. Over time I just began to accept that it would happen and that I couldn’t avoid these situations forever, so little by little I struggled through them. Now I’ve grown comfortable striking up conversation with just about anyone and everyone, though public speaking still intimidates me a bit.
I’m one of the few people I know that doesn’t get nervous over first dates. The reason for this is that I ask myself “what have I got to lose?” Half the battle is actually getting the date (which you don’t seem to have a problem with) and this means that the other person is already interested in you to start with. Most of the time it’s a guy I’ve just met and haven’t invested much time emotionally yet. Best case scenario, we hit it off; worst case scenario, we don’t connect or something hugely embarrassing happens, but either way I’ll have gotten out of the house for and evening and I’ll have a funny story to tell.