Matt Dillon: Never At A Loss For Company

Never-been-married Matt Dillon, 56, is perhaps the most notorious bachelor in Hollywood. He’s dated a lot of cute actresses – but until now his longest romance was with his There’s Something About Mary costar Cameron Diaz. They were together for three years until Cameron realized Matt had no interest in getting married. (They WERE crazy about each other!) Above, Matt is with his current girlfriend of 5 years, actress Roberta Mastromichele at the San Sebastian premier of a documentary he directed about a Cuban musician, called The Great Fellove. It remains to be seen if Roberta is “THE ONE.”

Photo Credit: BACKGRID-USA

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