Zimbio, in photo: Kim Porter, boyfriend Sean Combs
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1996 - July 2007

Sean and Kim dated on-and-off for over a decade. They famously broke up in 1999 and battled over child support for their son, and Diddy dated Jennifer Lopez for two years. Then, Kim and Sean reconciled in 2003 and were together for another almost 4 years. They had twin daughters in 2006 and called it quits for good in July 2007. "In ending this relationship, I made a decision that was in the best interest of myself, Sean and our family. I look forward to moving on with my life and my career, and wish him prosperity, health and happiness in life and in love. We will remain friends and committed parents to our children," Kim's statement read after the split.