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Jennifer Lopez and Diddy
Their relationship fizzled out faster than the trucker hat trend, but they were still together long enough to create a tabloid frenzy when they broke up amid rumors that Diddy was cheatin'. The rap mogul copped to his infidelities years later, admitting that he cheated on J.Lo with his baby mama Kim Porter. He also hinted that Jenny may have gotten around the block herself, saying "Jennifer did her thing on some things, too."
(Photo: Dave Hogan/Getty Images)
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