Matt Dillon
Matt Dillon has been in the business since 1979, establishing himself as a teenage idol before going on to star in films like Little Darlings and My Bodyguard early on in his career. He has had several girlfriends both inside and outside of the industry.
Despite having had many love interests, the famous actor still hasn’t tied the knot with anyone. He did date Cameron Diaz back in the 90s and has been dating Roberta Mastromichele, another actress, for more than four years already. Who knows, marriage just might be in the cards for these two in the future.