So the ideal is to adopt an "abundance mentality", right? One where you're so confident and successful that you really don't care if any individual reaction doesn't go your way. It takes a loooong time to get there if you're starting from a point of having dealt with rejection (whether explicit or imagined) for years.

I don't know if everybody's experience is the same, but I was a virgin well past the normal age and every attempt to get into the romantic game crashed and burned for one reason or another. Sure, the first few times can be explained away with truisms and platitudes, but after a while, the thought that you're just broken, undesirable, unlovable starts nagging at you. Every time that some girl dances with you then disappears without giving you her number, when that OKCupid date doesn't get a followup, it's all reinforcing that thought that there's just something wrong with you. Even when you do start seeing success, that thought, that fragment of your self-image, it stays with you. Shedding that part of your identity can be rough transition, and that's if you're aware of it and trying to move past it. Otherwise it just colors all of your future interactions.