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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.
The relationship fizzled after just a few months, and Kutcher went on to marry Demi Moore, and Murphy married Simon Monjack.
Actor Sean Penn and Madonna met and married in 1985.
Nicole Kidman recently told Net-a-Porter that in 2003 she had been engaged to Lenny Kravitz.
She confirmed it when asked about "Big Little Lies" co-star Zoë Kravitz saying, "Well, I knew Zoë because I was engaged to her father. " There's no bad blood between the two and she went on to say, "I love Lenny; he's a great guy." The late Brittany Murphy and Aston Kutcher met in 2003 while filming "Just Married." Rumors of their engagement circulated, but were never confirmed.
The pair originally met in 2006 on the set of Gym Class Hero's music video for "Cupid's Chokehold," Perry played Mc Coy's love interest.