Un-Break Our Hearts: Couples We Hoped Would Last

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  • Regina King, Malcolm-Jamal Warner
  • Vanessa Williams, Rick Fox
  • Chili, Usher
  • Russell Simmons, Kimora Lee Simmons
  • Heidi Klum, Seal
  • Shaunie O'Neal, Shaquille O'Neal
  • Jennifer Lopez, Marc Anthony
  • Lil Wayne, Toya Carter
  • Common, Erykah Badu
  • Diddy, Kim Porter
  • Kanye West, Alexis Phifer

Chilli and Usher

This R&B power couple fulfilled many fans' fantasies when they got together in 2001. Though their romance ended in 2003 (reportedly because of Ush's repeated infidelities), the exes have dropped enough hints in the press over the years to have us believing they never fully got over each other. Considering their both single now, maybe it's time to give love a (second) chance?  

(Photo: Evan Agostini/Getty Images)

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