When: February 2009 - July 2010
Kanye dated Amber Rose, who may be better known these days as Wiz Khalifa's future baby mama, for well over a year. During that time, Yeezy and the bald-headed beauty were arguably the hottest couple in entertainment.
Smash Probability: Not only did Kanye and Amber date for nearly two years, but they were regularly seen all over each other in public. PDA equals SIP: Smashing In Private.