Matt Dillon
Matt Dillon has been spotted on dates with multiple high-profile celebs, including Melanie Griffith. He's also known for his quick relationship with Denise Richards and Cameron Diaz. With all of these wonderful leading ladies on his arm, how come he hasn't tied the knot?
Dillon seems to move quickly through relationships. It's almost like he prefers the short flings over staying steady. Rumor has it that he has been dating famous choreographer Roberta Mastromichele for the last five years, which is pretty long for him!
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