When: December 2007
In 2007, Mayer set his sights on the stunning and bubbly Cameron Diaz. They quickly hit it off, as Mayer and the former Charlie's Angel were seen cuddling next to a crackling fireplace at New York City's swanky Bowery Hotel. This one we totally get. There's something about Cameron Diaz.
Smash Probability: Getting cozy near a fire in New York City at Christmas time? We know what happens next.