Fergie and Justin Timberlake
Sandra Bullock and Ryan Gosling
The pair met on the set of the movie “Murder By Numbers” and dated from 2002 to 2003. Another cougar situation, Bullock was 16 years older than Gosling. The two ended with a rumored nasty breakup that left Bullock heartbroken.
Tobey Maguire and Rashida Jones
The couple dated from 1997 to 1999, but Maguire broke up with Jones right before he began filming "Spider-Man."
Kim Kardashian and Nick Lachey
After divorcing Jessica Simpson, Lachey went on a date with the Kardashian sister as she was desperately trying to become famous. After one date, Lachey called it off claiming she tipped off the paparazzi about their location.
Hilary Duff and Shi LaBeouf
In another failed attempt at romance, Duff and LaBeouf went out once with it only ending in disaster. LaBeouf didn’t go into specifics, but called it “the worst date either of us has ever had.”