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

Big Sean and Naya Rivera

The Glee star gushed about her fiancè and planning their wedding in the February issue of Cosmopolitan, but by the time the issue hit the stands, Sean had announced the wedding was off. To make things even more awkward, the seemingly-amicable split quickly got ugly after Rivera accused her ex of stealing a watch on his way out of her house.  

(Photo: Jason Merritt/Getty Images for Dell)

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