Alexis Phifer

When: 2002 - 2008

Alexis and Kanye, who began dating on and off back in 2002, two years prior to Kanye's breakthrough smash, The College Dropout, got engaged in 2006. It seemed like a match made in heaven. However, after an 18-month whirlwind engagement, the two decided to go their separate ways in 2008. 

The grief over the breakup is what's said to have inspired Kanye's eclectically auto-tuned 808's & Heartbreaks album.

Smash Probability: They were engaged. Come on.