For me, it's more related to deepseated trust and self-worth issues (which is doubly fucked because I'm aware of them and don't really care that much); it took me six or seven years to get to the point where I knew a couple circles of people that I felt comfortable engaging in casual conversation with, and a large part of that was convincing myself not only that social contact beyond the handful of people I genuinely trusted and was interested in talking with was worthwhile, but that anyone else would care if I talked to them. I guess that's what four solid years of being treated by shit by pretty much everyone except close family and a couple of friends (one of whom I stopped hanging out with after it turned out that his primary amusement was vandalism and petty arson) does for you. And apparently, for most of my life I had a speech problem severe enough that even my parents often couldn't understand what I was saying, which would help explain in hindsight why I had issues making friends. (~birth through 8th grade; was in speech classes from preschool through 7th grade, when I finally got fed up with it and told the school administration flat out that I wasn't doing it any more and would rather not miss normal classes for something that I at the time thought I didn't need)
As for talking to girls I liked? Hell, I don't even know if I have a sex drive; every girl I was interested in was so because they were an interesting person to talk to, because they were intelligent and informed enough to debate stuff, and I don't honestly recall even wishing that I would motivate myself to pursue things further.
So yeah, socially, my life has been pretty much fucked, and I had maybe two or three geniune friends through the span of 3 years old through 16ish. I guess that might have been rageworthy for me at some point, but now? Eh, what's past is past. I've long since forgiven the people who made my life hell, and I don't see any point in regretting things I can't go back and change.