(Source: Zimbio, in photo: Cameron Diaz, boyfriend Matt Dillon)
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10. Cameron Diaz dated Matt Dillon
1995 - 1998

These two dated for three years, then called it quits just after filming "There's Something About Mary" together. Years later Matt admitted their relationship didn't work out because he wasn't ready to settle down. He said she was a "muse for me" in later years.