Matt Dillon, Age 55 – In a Relationship

Despite Matt Dillon being a known bachelor, there have been some women in the past that have made him want to settle. However, he never actually went ahead and tied the knot with any of them, but that doesn’t mean that he didn’t try.

Right when he was first getting into the industry, he dated Brook Shields. Their relationship ended in 1981. More than ten years later, he dated Cameron Diaz for three whole years. However, they split up shortly after There’s Something About Mary was released. He’s currently reportedly in a relationship with Roberta Mastromichele.