I had girlfriends from age 4-10 and 19-34 (my age, not theirs, sicko). That 9 years in between, I went on one date, which ended with a "let's be friends" speech. Two other girls asked me out, but I was too socially inept to know what to do -- I had a huge crush on a different girl, and I somehow thought that dating someone else would ruin my chances with her. That, and I froze up like a deer in headlights when a girl talked to me.
I'm pretty sure that I was mentally ill
I think back on some of my reactions to things and how I viewed the world, and it's just.... wow. Probably just immaturity and raging hormones I suppose, but I really had some misfiring neurons back then.