13. Alexis Phifer
The great Yeezy has been engaged more than once, and one of those lucky ladies was none other than the beautiful Alexis Phifer. The pair started their dating journey way back in 2002, and four years later Kanye proposed to Phifer on their vacation to Capri over a romantic dinner of lobster and pasta. The two were quite a couple and the media absolutely loved them because they lived an interesting, fabulous and fashionable lifestyle. They were always hanging around the fashion crowd since he loved fashion and she was a designer. His mother died while they were engaged and although they stuck together for about a year after, the relationship went downhill from there.
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