However, the actor was in a three-year relationship with There's Something About Mary costar Cameron Diaz, from to It's not certain whether the exes on this list are women that Matt Dillon has had sex with, but it's safe to assume that when two adults are going out, some action will inevitably occur. After a time, they decided to take their beverages and snacks to go. The former Entourage star wasn't shy about packing on the PDA with his mystery blonde companion Romantic: He opted for a dark grey v-neck shirt that he teamed with a pair of off-white jeans and black sneakers. Fans will also enjoy these sexy photos of young Matt Dillon. Mixed media' The Crash actor played the lead on M.