Un-Break Our Hearts: Couples We Hoped Would Last

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  • 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
  • Vanessa Williams, Rick Fox

Jennifer Lopez and Marc Anthony

Like a boricua Ken and Barbie, J. Lo and Marc were made for each other. After the longtime friends found love with each other after numerous failed relationships, it seemed like it would last. Well, old habits die hard. The pair divorced in 2001, but remain friendly to raise their two children and grow their many businesses together. Maybe once they each finish sowing their wild oats, they'll retire together.

(Photo: Charley Gallay/Getty Images for UNICEF)

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