Well, I've experienced the same thing from the opposite gender's perspective. I've been positively afraid of women my own age since I was 18 or so. I was pretty eager for romance and love in middle school through college and asked many girls to go out with me, but every single one of them rejected me. Probably had something to do with my Social Anxiety Disorder and Depression -- too nervous and hesitant, not confident enough, something like that. In any case, it took a toll. I stopped trying around the middle of college, and am now resigned to a very lonely life.