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Women Who Matt Dillon Has Dated

Updated June 14, 2019 158.2k views12 items

Got a thing for '90s TV stars? So do these famous women who have dated Matt Dillon, listed alphabetically with photos when available. Wondering who Matt Dillon has dated? This list features Matt Dillon's ex-girlfriends along with additional information about them, such as when they were born and what their profession is. Fans will also enjoy these hot photos of young Matt Dillon. These women come in all shapes and sizes, but what they all have in common is that they're all women who Matt Dillon has either dated or canoodled with. It's not hard to get jealous of these women that Matt Dillon has gone out with, so try your hardest to contain your envy.

If you're wondering who Matt Dillon's wife is, stop - he never married! However, the actor was in a three-year relationship with There's Something About Mary costar Cameron Diaz, from 1995 to 1998. 

Dillon has a pretty epic dating history that includes exes like Brooke Shields, Melanie Griffith, and Eliza Dushku. This list answers the questions, "What are the names of Matt Dillon's ex-girlfriends?" and "Who has Matt Dillon linked up with?"

It's not hard to imagine that his romantic life has been pretty good. It's not certain whether the exes on this list are women that Matt Dillon has been intimate with, but it's safe to assume that when two adults are going out, some action will inevitably occur. Who has Matt Dillon slept with? We can't say for sure but it's most likely all the women on this list.

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  • Matt Dillon and Denise Richards shared a steamy romance scene in the 1998 film Wild Things. They were also rumored to have got together off camera.

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    • There's Something About Mary co-stars Matt Dillon and Cameron Diaz dated from 1995 - 1998.
      Cameron Michelle Diaz (born August 30, 1972) is a retired American actress, writer and former model. She has frequently appeared in comedies throughout her career, while also earning critical recognition in dramatic films. Her accolades include four Golden Globe Award nominations, three Screen Actors Guild Award nominations, and a New York Film Critics Award. In 2013, she was named the highest-paid actress over 40 in Hollywood. As of 2018, the U.S. domestic box office grosses of Diaz's films total over U.S. $3 billion, with worldwide grosses surpassing $7 billion, making her the fifth highest-grossing U.S. domestic box office actress.Born in San Diego, California, Diaz was raised in Long...  more

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      • Matt Dillon dated his Drugstore Cowboy co-star Heather Graham from 1988 - 1989.
        Heather Joan Graham (born January 29, 1970) is an American actress, director, and writer. After appearing in television commercials, her first starring role in a feature film came with the teen comedy License to Drive (1988), followed by the critically acclaimed film Drugstore Cowboy (1989), which gained her initial industry notice. She then played supporting roles in films such as Shout (1991), Diggstown (1992), Six Degrees of Separation (1993), Swingers (1996) and on the television series Twin Peaks (1991) and its prequel film Fire Walk with Me (1992), before gaining critical praise for starring in Paul Thomas Anderson's Boogie Nights (1997) as porn starlet Brandy / Rollergirl. In 1999,...  more

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        • Matt Dillon and Brooke Shields were a couple from 1980 - 1981.
          Brooke Christa Shields (born May 31, 1965) is an American actress and model. She was initially a child model and gained critical acclaim at age 12 for her leading role in Louis Malle's film Pretty Baby (1978), in which she played a child prostitute in New Orleans at the beginning of the 20th century. Shields garnered widespread notoriety in the role, and she continued to model into her late teenage years and starred in several dramas in the 1980s, including The Blue Lagoon (1980), and Franco Zeffirelli's Endless Love (1981). In 1983, Shields suspended her career as a model to attend Princeton University, where she graduated with a bachelor's degree in Romance Languages. In the 1990s,...  more

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