In the past year and a half, I have been working to help a friend- who, despite being a very nice and rather handsome guy- is 21, never had a girlfriend, and still a virgin.

We have had some initial successes- he started dating a girl for about 3 months before they broke up, and he has gone out on 1 or 2 dates. He has been working on his wardrobe (which used to be nothing but anime and metal shirts), has become a lot more playful, self-confident, and has broadened his interests beyond the usual "nerd stuff". But that's IT in the past year (we still have to work on his serious temper problem)...

What really puzzles me is we go to a lot of places where there are plenty of cute chicks to meet: malls, Goth clubs, cafes, bookstores, parks, etc. and while we meet a lot of interesting women, we have some key problems: The only girls who seem to be willing to talk to him or seem attracted to girls are either TAKEN or turn out to be FLAKES. He can easily get a girl's phone number, but they either turn out to never pick up/call him, or in getting to know them he finds out they're in a relationship!

What do you think is making so that my cute and funny friend cannot attracted single girls, but is surrounded by flirtatious taken women, flakes, and gay men?!