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

Drake and Rihanna

As if the Rihanna-Chris Brown-Karrueche Tran love triangle wasn't awkward enough, RiRi threw another log in the fire when she rekindled her romance with rumored ex-fling Drake. The pair have been seen coupled up all over Europe and courtside at NBA games while poor Breezy sits in jail. He's at a safe distance now, but hopefully Brown's anger management lessons will come in handy when he's sprung and faces the awkward run-in with his ex and her new man.

(Photo: London Entertainment / Splash News)