I have dated before, but not much. The most significant relationship I've had, I sort of begged her to go out with me (to be fair to myself, I was pretty convincing), moved to another city to be with her, and was "contracting" as a job which really meant sitting around websurfing all day. There was no structure in my life and I couldn't hold things together, and after a few months she decided to break up with me and move 1000+ miles to go back to school. This was a formative experience for me and I'm sure it's related to my current anxieties.