Person 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. Fans will also enjoy these sexy 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 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.

Roberta Mastromichele is listed (or ranked) 1 on the list Women Who Matt Dillon Has Dated
Photo:  Dave M. Benett/Getty Images

In 2014, Matt Dillon began dating film choreographer Roberta Mastromichele.

Roberta Mastromichele is an actress. ...more

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Profession: Actor

Credits: The Tourist

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Melanie Griffith is listed (or ranked) 2 on the list Women Who Matt Dillon Has Dated
Photo:  Manfred Werner/Wikimedia Commons/CC BY-SA 3.0

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: 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

Also Ranked

#234 on The Best Actresses in Film History

#616 on The Greatest Actors & Actresses in Entertainment History

#293 on The Biggest Douchebags in Hollywood

#217 on Annoying Celebrities Who Should Just Go Away Already

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Hallie Eisenberg is listed (or ranked) 3 on the list Women Who Matt Dillon Has Dated
Photo:  Neilson Barnard/Getty Images

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, USA

Profession: Child Actor, Actor

Credits: The Insider, Bicentennial Man, Wild Child, The Goodbye Girl Paulie, + more

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Eliza Dushku is listed (or ranked) 4 on the list Women Who Matt Dillon Has Dated
Photo:  Michael Buckner/Getty Images

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, ...more

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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

Also Ranked

#74 on The Best American Actresses Working Today

#724 on The Best Actresses in Film History

#239 on The Best Actresses Working Today

#141 on The Most Overrated Actors of All Time

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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 ...more

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Age: 44

Birthplace: USA, Downers Grove, Illinois

Profession: Television producer, Model, Actor

Credits: Starship Troopers, The World Is Not Enough, Wild Things, Valentine

Also Ranked

#928 on The Greatest Actors & Actresses in Entertainment History

#205 on The Most Trustworthy Celebrities in the World

#66 on The Best Female Celebrity Role Models

#114 on The Most Beautiful Women in the World

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Cameron Diaz is listed (or ranked) 6 on the list Women Who Matt Dillon Has Dated
Photo:  There's Something About Mary

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, ...more

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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

Also Ranked

#64 on The Best American Actresses Working Today

#157 on The Best Actresses in Film History

#408 on The Greatest Actors & Actresses in Entertainment History

#109 on The Best Actresses Working Today

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Heather Graham is listed (or ranked) 7 on the list Women Who Matt Dillon Has Dated
Photo:  Peter Kramer/Getty Images

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 ...more

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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

Also Ranked

#243 on The Best Actresses in Film History

#569 on The Greatest Actors & Actresses in Entertainment History

#152 on The Most Overrated Actors of All Time

#91 on The Most Beautiful Women in the World

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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 ...more

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Age: 50

Birthplace: New York City, New York, United States of America

Profession: Actor

Credits: Man of Steel, Inside Out, Unfaithful, The Perfect Storm

Also Ranked

#37 on The Best American Actresses Working Today

#63 on The Best Actresses in Film History

#197 on The Greatest Actors & Actresses in Entertainment History

#208 on The Best Actresses Working Today

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