Un-Break Our Hearts: Couples We Hoped Would Last

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  • 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
  • Regina King, Malcolm-Jamal Warner

Russell and Kimora Lee Simmons

Admittedly, Kimora Lee Simmons and her mogul ex seem to get along better as exes than they did when they were married. But it's hard not to root for the lovers-turned-besties to get back together when they clearly keep ending up with the wrong people. It's like a reconciliation setup for a hip hop romantic comedy!

(Photo: Jerritt Clark/Getty Images)

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