True, Fell. In highschool there was one girl, Jenny, who I was completely wupped over. I would ask her out all the time (I think I asked her to every single dance, and a multitude of dates. ) I remember only actually going out with her once - although I can't remember where we went. The problem was that I was hardly ever rejected initially. Normally she would say yes, and then call later to cancel saying that "something came up, but I'd really love to do something some other time." My problem was that I actually believed that - even though this happened twice a week for four years.
I think that my main problem was that, in high school, I wouldn't ever date a girl unless I though she was marraige material. Consequently, I had an extremely narrow category of girls I wanted to ask out - and all three of them were either uninterested or hooked up with someone else. I did end up going on plenty of dates, but whenever some date opportunity came up, I would always ask the three of them, get rejected, and then move on to someone else.
On a different note, the year after high school, my friend and I (looking for a good use for the database program on our computer) made a Date-a-base (we thought the name was really clever). We entered all the girls we'd ever dated or wanted to date. Then, we could just ask the computer to, for example, give us a list of all brunettes who have green eyes and enjoy bowling, and it would pop out a list of names. It was never very helpful.