I once read about a very famous therapist who was trying to cure his shyness with women and he spent numerous days at a park asking out every woman who sat down on a bench next to him. And he got rejected a ton, but he also had some success, and came to realize what was making him so shy was the fear of rejection. And once he could deal with the rejection, he could overcome the shyness. So the point is, just get out there and start dating--the more practice you have, the better you'll get. Internet dating is usually a good way to ease into things, since you start off with the less-high-pressure email interaction. Rejection is going to happen--it happens to everyone--but the more you're out there, the less that will come to mean.