I've personally also been "socially awkward" in the past. It's easy to lack in social skills when you have self confidence problems. I guess the most important thing in life is to have self confidence, and to learn to not bother too much about what people think of what you do, or say.
And also, woman-wise, for those that don't really go out, it might be a good idea to try online dating. Since I wasn't really the type of guy that went out a lot, I've tried online dating for like 2 years, and that's how I met my girlfriend, Alexandra. Some people still have "prejudices" against online dating, but in fact, it's a very nice way to learn a lot about someone before meeting her, and to actually be able to meet people that want a relationship. And for "socially awkward" people, it's often easier to break the ice when talking to a girl behind a keyboard, at first.