Awkward Celebrity Dating Moments

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  • 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
  • LeToya Luckett, Kevin Durant

Rihanna and Chris Brown and Karrueche Tran

The most awkward love triangle in recent memory kept the tabloids fed for weeks on end. Chris Brown couldn't seem to make up his mind between his ex, Rihanna, and his ride-or-die chick, Karrueche. To make this particularly awkward, he confessed his indecision in a series of videos, which he posted to social media. Breezy did everything but take a poll of his fans to decide which chick to call his girl. 

(Photos from left: Allison Joyce/Getty Images, Steve Mack/FilmMagic, FameFlynet, Inc)

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