Awkward Celebrity Dating Moments

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  • 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
  • Justin Timberlake, Fergie
  • Rihanna, Chris Brown, Karrueche Tran

Khloe Kardashian and Lamar Odom

The demise of Khloe and Lamar's marriage was more tragic than awkward, but things definitely got weird when Odom, who's reported drug addiction and infidelities lead to the end of his marriage, did an impromptu freestyle on TMZ copping to cheating — all while he was actively trying to win back his wife. Wrong move, player.

(Photo: Lawrence Schwartzwald / Splash News)

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