Superstud: Or How I Became a 24-Year-Old Virgin by Paul Feig
This is by the fellow who was responsible for the TV show Freaks & Geeks. It details his adolescent years, focusing particularly on the dating part.
It's really funny, but in vaguely uncomfortable way because you're essentially laughing at the pain he went through. So if you have trouble with being empathetic (not like me, apparently) you might not enjoy it.