When: December 2007
Diddy’s relationship with Jude Law’s former fiancèe, Sienna Miller, was short but not so sweet. The two were mostly known for being caught partying together on multiple occasions—as well as once being caught together at breakfast the morning after—and they became easy fodder for the paparazzi even as they both denied hooking up. Their late-night crusades would soon come to an end, as would Diddy’s long-standing relationship with Kim Porter.
Smash Probability: