Awkward Celebrity Dating Moments

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  • LeToya Luckett, Kevin Durant
  • Reggie Bush, Lilit Avagyan
  • Justin Timberlake, Fergie
  • Rihanna, Chris Brown, Karrueche Tran
  • Ray J, Kim Kardashian, Kanye West
  • Coco Austin
  • Khloe Kardashian, Lamar Odom
  • DJ Khaled, Nicki Minaj
  • Shemar Moore, Toni Braxton
  • Jennifer Lopez, Ben Affleck
  • Amber Rose
  • Kim Kardashian, Kris Humphries
  • Big Sean, Naya Rivera
  • That Awkward Moment
  • Drake, Rihanna

Justin Timberlake and Fergie

It's no secret Timberlake has a thing for older women, but his romance with Black Eyed Peas singer Fergie was more Mrs. Robinson than Cougartown. Timberlake dated Fergie back in the 1990s, when she was 23 years old and he was just 16.  

(Photo: Frank Micelotta/Getty Images)

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