Matt, as he is quite famously called, has been hooked-up and also been in known relationships with quite a few women. His first reported relationship was with a woman, ten years younger to him, Seka who was one of the famous actresses of her time. After a short stint, he reportedly dated Karen Campbell for a while before they eventually got separated. His first girlfriend though, was actress Carole Mallory but their relationship’s start and end are still unknown. It is predicted to have been somewhere around 1970s.

His next few dates were supposedly actresses Sonja Morgan and Ellison Jordana but those were merely brushed off as rumors and nothing ever surfaced above. He got into his second relationship with actress Ellen Barkin, which didn’t last long either. His next relationship though was with the then, new entrant into the film industry, Brooke Shields. They dated and were in a relation for just around the period from 1980-81, before breaking up. It took a long time for Matt to get into another relation. His relationship with Heather Graham started in 1988 and lasted for just around a year.

The next relation he had, got him more fame than he would have anticipated himself. He got hooked with Hollywood hottie Cameron Diaz famous for her roles in films that have earned acclaim all around and it was reportedly her second boyfriend. The two were seen quite often, in various red carpet events and for a while, their affair had become the talk of the town. The couple appeared in a few films together, and the two had supposedly met on the sets of a film as well. Their relationship went quite well till conflicts made separation evident. They separated almost immediately after the filming of There’s Something about Mary got over. It was a shock for everybody as gossip circles were rife with rumors of a supposed marriage but such a thing never panned out.

Matt eventually stopped acting for a while before starting to act again in early-2000. The effect of the break-up seemed to be quite evident in Dillon’s professional life too. His big breaks eventually faded away and gave away for smaller roles that didn’t really help his booming career. His next big film came with Crash that also earned an academy award nomination. He got back on track and was reported or rather rumored to be dating young actors like Eliza Dushku and Hallie Eisenberg in 2006 and 2009 respectively but these were never really taken seriously by the media. His life too seemed to be back on track and with the news of him starting to date Roberta is news to cheer, for all his fans. Although in quite a few relations, he never had a divorce since he never married!