I think there’s been some good advice in this thread. If I were single now, this would make me want to go out there and try some of the suggestions mentioned herein.
I’m about as socially inept as the next doper, but I think I’d like to offer a tidbit of advice myself, although it probably won’t do a whole lot for my fellow socially inept boobs.
In a nutshell, I think the phrase “grain of salt” summarizes what I’d like to suggest. I know that it’s been this way in the past with me, and many people I know - you get nervous. It’s very common. But think about this from a third-person perspective for a moment. Imagine this is a movie, and you’re watching the protagonist (you), and he’s in some dire situation, like he just found out the world is going to end tomorrow but he can’t tell anyone, so he wants to make the most of his last night on earth.
He sees a gorgeous girl over at the bar, and as she turns, she catches his eye and smiles. Now, he’s normally not very good at this whole ‘talking to women’ thing, but he manages to keep in mind that this is his last night on earth, and he best make the most of it. He’s determined to find a girl that he can connect with, even though it’ll only be for a few hours, and of course, have incomparable sex with. She may or may not be, on paper anyway, the ‘perfect’ girl for him. It doesn’t matter. If they don’t compliment each other perfectly, so what? If he spends the whole night looking for the girl that fits him perfectly because of this reason or that, he’ll probably still be alone at the end of the night and have missed many great opportunities. He rationalizes that there are plenty of other women in this bar, and in many other bars, and so on. The night is still young. If she turns him down, so what? He won’t remember it tomorrow. And there are so many other desireable women out there; if she doesn’t work out, one of them will. Again, he realizes it won’t last forever, because the world is ending. They don’t have to be a perfect match.
So he’s managed to convince himself that, after tomorrow, what this girl thinks of him won’t matter. He smiles slightly. As she turns back toward the bartender, he strides toward the bar.
“Hi,” he says, with a slight smile. “I’m Andy.”
It might work the first time, it might not. But because he’s not fixated on one girl in particular and already worrying about what she’ll think of him, he eventually prevails. They may not be perfect for each other, but they’re attracted to each other and genuinely interested in each other. And so, he has the most amazing night ever, the last night on earth before the world ends.
…except, this is a movie, so you know the world doesn’t end. (Duh)
Maybe it’ll last, maybe it won’t. Maybe they’ll get married and live happily ever after, maybe they’ll have a huge fight and break up. If they do, they’ll both go out and find someone else, until eventually, they find someone to spend the rest of their live with. 
Man, that was really long. I haven’t rambled like that in a while. Anyway, take it with a grain of salt. Practice with people you know, until the sight of a pretty face and some nice boobs doesn’t make you go weak in the knees, and you can actually have a conversation with them. And try to remember that you have nothing to lose. If she shoots you down, she won’t remember you later, unless you just make a complete ass of yourself. It’ll be over and done and you’ll be talking to someone else that will give you the time of day.
Oh, and let her talk. If you talk some (which is more than ‘not at all’) but let her do the majority of the talking, you’ll be a good listener. You’ll get your chance to talk, and you’ll recognize it when it comes, but turn it around fairly quickly. If women don’t get to say anything for a long period of time, all that talking energy will become pent up inside them and they’ll explode. :smack: