Recently 29 and on my 5th breakup. #1 I didnt care about. She was very materialistic and no fun. (She ended up breaking up a family of four by getting with a rich dude 25 years older than her when she was 18) # 2 messed me up a little bit, maybe like a month. She had issues with addiction. #3 messed me up for a good three months. She was a hardcore lover of Kurt Kobain and idolized the Montage of Heck... this lead to her having serious depression issues. #4 was by far the worst. A good 8 months of being messed up. I begged, I became her friend, we had friend sex, and it all just messed me up even more. First woman I could see a future with, and thought I might love. She left to pursue a modeling career.