Time for self-examination

I've been thinking lately about where I am in my life, and what I still have left to work on in myself. My biggest problem has always been knowing how to act around other people. Because of this, I often feel like I haven't lived as much as other people my age. I don't have any stories about crazy things I did with my friends in high school, because I didn't really have any friends in high school. I don't even have that many bad relationship stories, except for one, and even that wasn't really a relationship. I know a lot, but almost all of it is from books. I heard the term "educated virgin" in a song once, and that's exactly what I am. I knew the basic facts and had heard anecdotes about life experiences like love and sex long before I ever experienced them for myself. Since I turned 21, I've tried to make up for my lack of life experience by throwing myself into clubs, casual sex and meeting new acquaintances through old ones. Even with people in my life that could now almost be considered friends, I still don't feel like I can call or email any of them to ask for advice or even to hang out (a lot of people I've met at the club live in Virginia anyway). Even after finding a writing group, we've stopped meeting, and I haven't seen the group of writers that could become compatible friends in weeks.
After a lot of thinking, and a conversation with a friend, I know that my problem is that I'm afraid to take risks, to put myself out there. I can in a superficial sense, going to a club and briefly talking to someone, but I still can't get below that surface to find a true friend. So I took one step, however small: I emailed the members of my writing group to arrange a meeting. To most people, this would be nothing, even standard behavior, but to me its huge, taking the first step without waiting for someone else to approach me.
What I need to do now is really think about what I want out of life, now that I've got my "living experience" out of the way. Through my times at Bound and Entre Nous, and going to college in Boston, I've seen what exciting things life has to offer, but what elements of it do I really want? I probably won't be going out this weekend, because I have so much thinking and self-analysis to do. What is it about the one or two guys I just can't get over that makes me crazy? How do I go about finding friends who are compatible with me and don't make me wonder why everyone in the world is so stupid, the impression I get from most of the people I've met in my life. And most of all, what am I so afraid of?