2015

NICOLE RICHIE

Richie and Jenner went from childhood pals (her dad Lionel Richie, a longtime friend of his parents, was there when he was born) to grown-up sweethearts in August 2006. And the Simple Life star got his mom's seal of approval. "I think they're very cute," Linda Thompson said. "Will they get married? Who knows." Uh, we do. The couple split that October, though Richie posted a message to her MySpace – MySpace! We were ever so young? – insisting "we were never really together … my heart was never in it."