Kanye enjoyed a few romances of his own, pre-Kim. Very serious was his relationship with designer Alexis Phifer whom he proposed to over a lobster and pasta dinner in August 2006 on the beautiful island of Capri. They had dated off and on since 2002. Their engagement lasted eighteen months. “It’s always sad when things like this end, and we remain friends,” Phifer told PEOPLE. “I wish him the best in his future and all of his endeavors. He’s one of the most talented people I’ve ever met.” Alexis Phifer did not seek the limelight like Kanye’s other flames. He promised his late mother Donda that he would marry her to make their relationship official.