When: July 2007
Diddy and Cruz have been friends since June of 2005, when she signed on to model in one of his Sean John ad campaigns (peep the supersexy shots here). But things got interesting in June 2007 when the two were out at at the famed Chinese spot Mr. Chow in Los Angeles. According to reports, Diddy had his eyes fixated on Cruz the whole time. But he had some competition for Ms. Cruz’s affections from his homeboy Pharrell Williams, who showed up and decided to sandwich Penelope between them. So Diddy did what Diddy does, and made sure Cruz rode with him to the Roosevelt Hotel for a Prince concert. Hmmmm...Prince records and Spanish model/actresses is a dangerous combination for any man to handle. Put them in a car together on the right night, and your guess is as good as ours...
Smash Probability:

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