I've got the gf's 3 kids, the middle one is an aspergers kid, he's 13. I have a hard time dealing with people, always have 5'9" 127 lbs. His difficulties are mind boggling. Eric Raymond (The Cathedral and the Bazaar) has a how to on dealing with social interactions for nerds. It's pretty good.
The assholes do get the girls, aggressiveness (not to drastic) is an important trait for males, dealing with other males, and as a show of strength for women, it is ridiculous, but true.
Most of my friends are from high school. I'm ingratiating enough to get social interactions and have buddies in college (I'm 35 going to U of Mich) but picking up women has always been a problem. I have picked them up on occasion, but the normal stories that folks tell, flirting and all are still beyond me. I've found being pleasant and having interesting info (from slashdot and IEEE mags, pravda.ru, etc.) helps to get me into conversations. Traveling and having the ability to tell people about the places I've been is useful too.
On the other hand I have spent weeks and moths without talking to anyone outside of work, and even weeks when I wasn't working not talking to anyone. It never bothered me, but I did have a cat to keep me company.
Watch some T.V. high neilson rated shows, so you can get in the conversation about current events such as they are (most people don't care about the world outside of their own very local interest)
The show House had a brilliant insight in season 1 or 2, House (The head doctor with a aspergers-ish personality) tells the hot assistant doctor that he hired her because she was gorgeous. The after a pause explains it's because she didn't need to do the hard work of becoming a doctor to have the easy life, because she could have been a model, and she did anyway, which shows her drive.
The sad truth is that most good looking people are also fairly smart, good genetics seem to be blessed on some. The slightly smarter are the MBA type folk, and next are engineers, finally the super smart are usually the scientist and the mathematicians. That is why the news stories of the hot math teacher decides to take home the 15 year old boy. She's in the same group, except she is hot, and has had to deal with asshole guys, and doesn't like it. She's just as socially inept.
I don't really know where I'm going with this, but take heart, you are not alone, it's not hopeless, but it's not easy either.
One last thought, if you are in a metro area, take an acting class, learn how to fake confidence and learn some of the social stuff from those people, they will be better at being able to spot and explain those deficiencies than most.
Good luck.