Awkward Celebrity Dating Moments

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  • 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
  • Shemar Moore, Toni Braxton
  • Jennifer Lopez, Ben Affleck
  • Amber Rose
  • Kim Kardashian, Kris Humphries
  • Big Sean, Naya Rivera

That Awkward Moment

We've heard time and again that Hollywood is a lot like high school, which means celebs' dating mistakes and mishaps tend to follow them for years. Inspired by one of our favorite recent comedies, That Awkward Moment — which drops on DVD May 13 — we look back at some of the most awkward celebrity dating moments.

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