Over the last few weeks I've become despondent over my situation: namely, not having experienced what so many people my age take for granted. People my age seem to have been in strings of relationships, take sex for granted, etc, whereas I haven't had any experience in that regard. Well, I did have a girlfriend briefly back in 2005, and I made out with her/felt her up, but, uh, it lasted two weeks when she dumped me for someone else.
I'm not sure what the exact cause of my situation is, but there are several factors. I seem to possess all the symptoms that come with "avoidance personality disorder" but I'm honestly not sure whether that's a consequence of social failure or something innate. Namely, I never exactly fit in in my school days, despite looking normal. I did not really have friends in high school -- I had peers with whom I had cordial relations, and they were from all high school social groups: Nerds, jocks, normal kids, theater geeks, etc. I didn't go to a single dance or sporting event. It did not help that the area I went to school in was solidly middle/upper-middle class and my family was headed by a single mother bringing in 30k. I always felt alone.
After high school, I went to community college, earned a two year degree and drifted for a long time working odd evening jobs. For some reason during that time my virginal situation didn't bother me.
Here is where I became despondent: My younger brother went off to university and in his first year there banged several chicks, one of them indisputably attractive whereas I've never had any woman express interest in me. That started making me question my circumstance and made me realize how stunted I've become. When I assessed the situation, I acknowledged that my personality is not very attractive, that I'm not funny or that much of an entertainer, that I'm someone who is ever so anxious and fearful of people. I realized there is not much I can offer any woman I'd find attractive other than a desperation to be intimate with her. And I feel pathetic for caring about it so much.