Dated: Shaun White, U.S. Snowboarding Team (2010 Olympics)
When: June-Present

Snowboarder and redhead Shaun "Flying Tomato" White, who met the supermodel at her Maxim cover party and cheered on Michael Phelps with her at the 2012 London Olympics, is not supposed to get this sort of action. Even if he is the best snowboarder in the world. Our hat is off to him, may she never come to her senses.