When: August 2010 - September 2010

Though this relationship was brief, Kanye did spend a good deal of time with this former Victoria's Secret Angel, who was the star of his "Runaway" video, after his relationship with Amber Rose had ran it's course. Amongst other places, the two were spotted cozying up next to one another at the 2010 US Open.

Smash Probability: A gorgeous fashion model from the Cayman Islands? If he didn't at least try, he's nuts.