Hit on different women, get used to talking to women without expectations and just be funny/engaging. If you're actually into the women you go for, when she says too old/too smart/etc. that just means try a bit more (just don't go too far, and by doing, you learn where that is). Some mutual interest is fine, and don't be afraid to be a total geek - lots of girls out here like that.

One thing that really helps: learn to dance, get some rhythm, and get in better shape. Most women like a nice ass just as much as we do.

The Jocks get the pussy, so yes they are the fittest, and so long as they continue getting laid, why change? The nerds and geeks around here (seattle) do pretty well for them selves, but the secret is this: own yourself and don't take any shit and be attractive - you will get some too. You don't have to be a jock or a meathead, but it helps to be in decent shape and have some physical skill (unless you like disappointing your sackmates).

All that pretend crap you're talking about is just getting in the way - bail on it, find what makes you happy and just TALK TO THEM LIKE THEY'RE NORMAL.

you misspelled ipod. Itunes is awful and put me off of apple stuff for years. It's heavy handed and buggy, and really the worst thing about my mac experience.