Women Who Matt Dillon Has Dated

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Got a think 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. 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.

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

It's not hard to imagine that his sex life has been pretty good. 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. 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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  1. 1
    Melanie Griffith is listed (or ranked) 1 on the list Women Who Matt Dillon Has Dated
    Photo: user uploaded image
    In 2014, Matt Dillon and Melanie Griffith were spotted going on a dinner date in Rome.

    Melanie Griffith is an American actress. The daughter of actress Tippi Hedren and former stage actor Peter Griffith, she rose to prominence for her role in Brian De Palma's Body Double, which earned her a National Society of Film Critics Award for Best Supporting Actress. Griffith's subsequent ...more

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    • Age: age 58
    • Birthplace: New York City, New York, United States of America
    • Profession: Film Producer, Model, Actor, Voice acting
    • Credits: Working Girl, Lolita, Automata, Cecil B. DeMented
  2. 2

    Roberta Mastromichele

    Roberta Mastromichele is listed (or ranked) 2 on the list Women Who Matt Dillon Has Dated
    Photo: user uploaded image
    In 2014, it was reported that Matt Dillon was dating Roberta Mastromichele.

    Roberta Mastromichele is an actress. more

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    • Profession: Actor
    • Credits: The Tourist
  3. 3
    Rumor has it that Matt Dillon dated Hallie Eisenberg in 2009.

    Hallie Kate Eisenberg is an American actress. more

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    • Age: 23
    • Birthplace: East Brunswick Township, New Jersey, United States of America
    • Profession: Child Actor, Actor
    • Credits: The Insider, Bicentennial Man, Wild Child, The Goodbye Girl, Paulie, + more
  4. 4
    Throughout 2006, Matt Dillon was frequently spotted with Eliza Dushku.

    Eliza Patricia Dushku is an American actress known for her television roles, including starring as Faith on Buffy the Vampire Slayer and its spinoff series Angel. She starred in two Fox series, Tru Calling and Dollhouse. She is also known for her roles in films, including True Lies, The New Guy, Bring ...more

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    • Age: age 35
    • Birthplace: Watertown, Massachusetts, United States of America
    • Profession: Businessperson, Television producer, Actor, Voice acting
    • Credits: True Lies, Wrong Turn, Bring It On, Jay and Silent Bob Strike Back
  5. 5
    Denise Richards is listed (or ranked) 5 on the list Women Who Matt Dillon Has Dated
    Photo:  Wild Things
    Matt Dillon and Denise Richards shared a steamy sex scene in the 1998 film Wild Things. They were also rumored to have hooked-up off camera.

    Denise Lee Richards is an American actress and former fashion model. She has appeared in films, including Starship Troopers, Wild Things, Drop Dead Gorgeous, The World Is Not Enough as a Bond girl, and in Valentine. She played Monica and Ross Geller's cousin on Friends. From 2008 to 2009, she starred on ...more

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    • Age: age 44
    • Birthplace: Downers Grove, Illinois, United States of America
    • Profession: Television producer, Model, Actor
    • Credits: Starship Troopers, The World Is Not Enough, Wild Things, Valentine
  6. 6
    There's Something About Mary co-stars Matt Dillon and Cameron Diaz dated from 1995 - 1998.

    Cameron Michelle Diaz is an American actress, producer and former fashion model. She rose to stardom in the 1990s with roles in The Mask, My Best Friend's Wedding and There's Something About Mary. Other high-profile credits include Charlie's Angels and its sequel Charlie's Angels: Full Throttle, voicing ...more

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    • Age: age 43
    • Birthplace: San Diego, California, United States of America
    • Profession: Model, Actor, Voice acting
    • Credits: There's Something About Mary, Shrek, Gangs of New York, Being John Malkovich
  7. 7
    Heather Graham is listed (or ranked) 7 on the list Women Who Matt Dillon Has Dated
    Photo: user uploaded image
    Matt Dillon dated his Drugstore Cowboy co-star Heather Graham from 1988 - 1989.

    Heather Joan Graham is an American actress. After starring in various commercials, her first starring role came in 1988 with the teen comedy License to Drive, followed by her breakthrough role in Gus Van Sant's critically acclaimed 1989 film Drugstore Cowboy. She then played a number of supporting roles ...more

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    • Age: age 45
    • Birthplace: Milwaukee, Wisconsin, United States of America
    • Profession: Activist, Television producer, Fashion Model, Actor, Writer
    • Credits: The Hangover, Austin Powers: The Spy Who Shagged Me, From Hell, Boogie Nights
  8. 8
    Diane Lane is listed (or ranked) 8 on the list Women Who Matt Dillon Has Dated
    Photo:  The Big Town
    Matt Dillon and Diane Lane were rumored to have dated in the 1980s.

    Diane Lane is an American actress. Born and raised in New York City, Lane made her screen debut in George Roy Hill's 1979 film A Little Romance, starring opposite Sir Laurence Olivier. Soon after, she was featured on the cover of Time magazine and dubbed "the new Grace Kelly". She has since appeared in ...more

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    • Age: age 50
    • Birthplace: New York City, New York, United States of America
    • Profession: Actor
    • Credits: Man of Steel, Inside Out, Unfaithful, The Perfect Storm
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