When: August 2001
Long before she was known as Bruce Willis’ wife, Emma Heming was better known as one of Diddy’s favorite weekend hobbies. Heming, a British model and actress, first turned heads in a Details photo layout with Puff in August 2001 (NSFW), as the scantily clad female tugging on his multiple chains. We’re not sure how long they were dating, but media outlets like People referred to Heming as Puff’s girlfriend. So in other words, Puff got over his breakup with J. Lo by twisting out yet another bad-ass chick.
Smash Probability: