Yeah this problem is really a self-worth issue.
You are not going for the girls you really deserve, because you don't feel you deserve them. Going for women more messed up than ourselves is simple way of trying to feel good about ourselves.
I did this when younger, I only dated messed up girls. Essentially I was a magnet for girls who were raped, sexually abused, beaten up, or had major issues, that generally drunk too much, took drugs, or were completely nuts.
Your mates may think its cool but dating a bikini model with no job gets pretty old pretty quickly...
I had to first take myself out of the dating arena, work on myself, increase my standards, and take a few leaps of faith in going for women who were completely awesome.
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