The Sweetest Thing Was the Engagement Ring, in 1999-2003
Ok, let's be honest. Any fan of MTV's "My So-Called Life," would've jumped at the chance to date Jared Leto, aka Jordan Catalano on the show. Cameron Diaz was the lucky girl. The couple began a quiet romance in the winter of 1999, which led to a private affair lasting four years. In 2003, engagement rumors were set ablaze when Cameron wore a $15,000 rose-cut diamond ring to the 2003 Golden Globes. But their love didn't last long enough for us to see if Cam was going to walk down the aisle. The couple split soon after.