When: April 2011

After checking her out at a Victoria's Secret VIP party, Kanye was reportedly smitten with Candice Swanepoel, a stunning South African Victoria's Secret Angel. Multiple sources reported that Kanye's people were scrambling to get Swanepoel's digits for Ye after the event.

Smash Probability: We never heard anything else about this one, so we're assuming it wound up as a crush, not a smash.