Awkward Celebrity Dating Moments

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  • 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
  • Justin Timberlake, Fergie
  • Rihanna, Chris Brown, Karrueche Tran
  • Ray J, Kim Kardashian, Kanye West
  • Coco Austin
  • Khloe Kardashian, Lamar Odom
  • DJ Khaled, Nicki Minaj

Kim Kardashian and Kris Humphries

Kim's short-lived nuptials to NBA player Kris Humphries was embarassing enough without the fact that their entire relationship was documented for reality television. The re-runs of Kim's Dream Wedding were still running when the reality star filed for divorce.

 (Photo: Fame Pictures, Inc)

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