Awkward Celebrity Dating Moments

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  • 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
  • Ray J, Kim Kardashian, Kanye West
  • Coco Austin
  • Khloe Kardashian, Lamar Odom

Jennifer Lopez and Ben Affleck

We're sure putting her boyfriend in her music video seemed like a good idea to J. Lo at the time, but now that the couple has imploded, the "Jenny From the Block" clip is just a constant reminder of a relationship they'd likey both rather forget. We're sure the married father of three will have a good time trying to explain the sexy video to his kids one day.

(Photo: Courtesy of Sony BMG Music)

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