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"America's Got Talent" host Nick Cannon dated Kim Kardashian from September 2006 to January 2007.He went on to tell Howard Stern that he broke it off after she lied to him about her infamous sex tape.
Brad Pitt and Gwyneth Paltrow began dating in 1994 after meeting on the set of "Seven." He popped the question two years later, but they never made it down the aisle as they called off their engagement in 1997.Naomi Watts and the late Heath Ledger began dating in 2002, when they worked together on the Australian film "Ned Kelly." People magazine reported the couple dated for 16 months until their split in 2003.In the early 2000s, Nicole Richie was dating Good Charlotte singer Joel Madden, so it makes sense that her then-best friend, Paris Hilton, would date Madden's twin brother and bandmate, Benji Madden.Jack Nicholson and Lara Flynn Boyle had an on-again-off-again relationship from 1999 through 2006.Boyle, who had been dating actor David Spade, told Vanity Fair that Nicholson asked her out in front of him.