Download/buy "The Game: Penetrating the secret life of pickup artists." by Neil Strauss.

It's a pretty good read, showing the highs and lows of becoming someone who can pickup women with minimal effort.

Just started the follow up book, "Rules of the Game." by Neil Strauss.

This is more of a self-help book, where you fill out your goals etc, and follow a day by day timeline where you do something to improve your confidence and stuff like that.

If anything it helps give up your fear of rejection and gives your confidence a boost.
So you've got nothing to lose really.