When: 1996 - 2007
Despite their on-again, off-again status, Porter was Diddy’s main squeeze for a decade. He and the former model met before the glory days of Bad Boy, when Diddy was a flourishing A&R and Kim was a receptionist at Andre Harrell’s Uptown Records. Although they never got married, over the course of more than a decade Kim would mother three of Diddy’s children (their son Christian and twin girls D’Lila and Jesse James). In 2007 the pair broke up for good and in dramatic fashion, but things seemed amicable afterward as both parties released warm-hearted public statements about the other. However, Porter would later tell Essence that Diddy’s infidelity (more on that later) had something to do with their breakup.
Smash Probability: