Awkward Celebrity Dating Moments

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  • 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
  • LeToya Luckett, Kevin Durant
  • Reggie Bush, Lilit Avagyan

Ray J and Kimye

Kim Kardashian has come a long way since that infamous sex tape, but it seems her co-star Ray J just can't resist bringing up the past. Even though his ex is clearly happy with her new man Kanye, the R&B singer felt the need to mark his terrority last year with the single "I Hit It First." Keep it classy, Ray J.

(Photos from left: Mark Davis/Getty Images for BET, Michael Buckner/WireImage)

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