Well...
My parents were.... well, they shouldn't have been married, so my up-bringing left me kind of emotionally void and socially inept. I've worked hard to fix the later problem. I just don't think like other people because of the former, which is a problem I haven't been able to overcome quite yet.
I have self image problems. I'm overweight because of the eating addiction I'm trying to fight - I need to drop about 40-45lbs. I have a huge gap in my front teeth because my parents couldn't afford braces and I haven't been able to afford any cosmetic surgery for it yet. I can't seem to get a tan no matter what I try, so I'm always pasty white... and I have a wierdly shaped head (which I've partially fixed by growing a goatee). I actually had a picture taken of me just this past week at the bi-weekly karaoke session I go to... and I look like a walrus' ghost in it. The women I spent the entire night talking to and dancing with on Tuesday wouldn't even say a word to me Thursday.
This particularly frustrates me because I consider myself to be a pretty well-rounded guy. I have a steady job (two, actually), I have a diverse set of hobbies(chess, digital photography, classic literature, re-learning French, martial arts...), and I like to think I'm a pretty good guy. I've never cheated in a relationship, I try to treat my friends well, and I generally hold myself to a personal code of honor. Twice, I've actually put myself between my women friends and guys that were acting pretty scary towards them. I don't understand why I have so many problems with women.... all I can conclude is that I'm ugly as sin.
I've got baggage from a relationship that ended two years ago, which factors in... somehow. After I secretly started pricing engagement rings, she dumped me... but we continued to live together since neither one of us wanted to break our lease. After a few weeks, she started dating women... and, well, the wall between our bedrooms was thin. I've been looking to date again and have tried once since... but it was with someone who was a very bad idea and that relationship was doomed from its onset.
Also, because of my academic background....well, I've sort of lost respect for the majority of humanity. I find most people tend to be fairly unpleasant folks pretty much all of the time... at least most of the people with whom I routinely interact. Arrogant, selfish, petty, superficial, and jealous.