Well obviously it's not relevant to me any more, but when I was a youngster it was absolutely about confidence.
I was fine with the humour and chatting up thing. Didn't mind approaching girls at all. It was getting to the next stage that was always the problem. I was convinced that girls would only like me as a friend, and wouldn't consider, you know... doing it. Especially as the blokes they DID fancy always seemed to be very unlike me - they were usually handsome musclebound sporty oafs, and I was this weedy geek (as I perceived myself).
I never dared "make a move" because I was convinced they would either laugh at me, or explain apologetically that they liked me, but not in THAT way. I was so scared of rejection and humiliation I usually didn't try.
The result was that I ended up with lots of platonic female friends, and (as I discovered later) quite a few that were offended because they thought I had rejected them - when I was blissfully unaware they were interested. They probably thought I was gay (and I was very much not gay!)
I got over it, of course, but not really until I was in my early 20s. Looking back, I still feel quite sad at the number of lost opportunities - and I have considerable sympathy for young guys in that situation now.
As ME demonstrates, women have no idea of how daunting the whole dating thing can be for some guys.
I do understand it. Honestly. I go out with my guy friends all the time and watch them try. Sometimes I help them. I understand everything you are thinking. I am simply saying that the way you guys perceive it is a bit of an exaggeration. You yourself later realized you had missed out on a lot because you convinced YOURSELF it wouldn't happen instead of just trying. And in the end it was your own thoughts that basically cock blocked you. All I am saying is, stop letting the fear of rejection get in the way of a possible good time. I've been rejected. I know how it feels. Didn't stop me from trying again.
I'm with mooney, it's all about confidence. When your confidence is low you see things in the same light that you do when you ARE confident. I missed out on a number of opportunities when I was younger because my confidence was down, but as I've got older I notice women looking more. I dont know whether that's me noticing because I'm confident or because I'm more confident in myself, making women look at me more :S
Also, i think you get to know yourself a little better as you get older and that can give you a little more confidence, it has for me, although I'm still don't exactly exude confidence.
On the rejection thing, I had a mate that would get his oats every night he went out. He was the envy of all his mates, but he'd actually get rejected a lot more than anyone else. He'd get knocked back 5 times out of 6 on night out, but wouldn't let it affect him, he'd just didn't let it knock him.