When: 2008
We’re not sure when Diaz and Diddy started to pal around, but in March 2008 they were caught eating together in Los Angeles. Then in April they popped up again, this time partying in New York, where they were said to have disappeared into a room together for about 20 minutes. And in May, Diaz was seen spoon-feeding Diddy some of her bread pudding at a party for Prince. When asked about the rumor, Diddy would only admit to them being friends, as usual. Dude definitely knows how to woo the Hollywood chicks, but you tell us how resistant you would be if Cameron Diaz was spoon-feeding you some bread pudding. That shit is delicious, B!
Smash Probability: