Women Who Matt Dillon Has Dated

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.

  • Matt Dillon's relationship with Roberta Mastromichele, an Italian actress, began in late 2014 following their unexpected encounter at the Rome Film Festival. Both having shared love for cinema, the festival marked the beginning of their courtship, which led them to embark on a romantic journey together. Although they primarily split their time between Rome and New York, they kept their relationship away from the spotlight, allowing their love to bloom out of the public eye. They have been dating since 2014.

    Roberta Mastromichele is a well-respected Italian actress, known for her versatility and strong performances in both television and film. Over the years, she has gained recognition for her talent, effectively carving out a name for herself in the competitive world of European cinema.

  • Melanie Griffith
    Photo: Manfred Werner / Wikimedia Commons / CC BY-SA 3.0

    In the early 1980s, Matt Dillon and Melanie Griffith met on the set of a movie where they were co-stars. Their mutual respect and admiration soon transformed into a romantic relationship that lasted for a few months. The duo maintained an amicable connection even when their romantic relationship didn't last for too long. They separated in 1982, marking the end of their brief but vibrant relationship.

    Melanie Griffith is a renowned American actress, acclaimed for her roles in films like Working Girl, for which she received an Academy Award nomination. Her prowess in acting and her charismatic on-screen presence has made her a prominent figure in Hollywood.

  • Hallie Eisenberg

    Known for her roles as a child actress, Hallie Eisenberg dated Matt Dillon for a brief amount of time. Rumors of their romance began swirling around in 2009 when they were spotted at multiple events together. Even though their relationship was somewhat transient and not officially confirmed, the pair left an impressionable impact on each other. They amicably decided to go separate ways in the same year, 2009.

    American actress Hallie Eisenberg is widely recognized for her roles in movies like Paulie and Beautiful, which established her as a talented child actress. As she transitioned into adult roles, she continued to showcase her adept acting abilities.

    • Age: 31
    • Birthplace: USA, East Brunswick Township, New Jersey
  • Matt Dillon's relationship with Eliza Dushku started in 2006, they were introduced to each other through mutual friends and soon started dating. Their romance, however, was relatively short-lived with their relationship ending towards the end of the same year. Despite their relationship being ephemeral, they both respected each other's space and career and decided to split on good terms.

    Eliza Dushku is a talented American actress, best known for her roles in TV shows like Buffy The Vampire Slayer and movies like Bring It On. Over the course of her career, she has made a significant impact in Hollywood with her unique and engaging performances.

    • Age: 42
    • Birthplace: Boston, Massachusetts, USA
  • Matt Dillon dated Denise Richards in 2006, after the pair met at a mutual friend's party. Their relationship was well-publicised due to their high-profile status in Hollywood. However, they only dated for a brief period before they mutually decided to part ways later that same year.

    Known for her roles in movies like Wild Things and The World Is Not Enough, Denise Richards is a popular American actress. She has gained an immense fan base due to her various roles in film and television, further solidifying her celebrity status.

    • Age: 52
    • Birthplace: Downers Grove, Illinois, USA
  • Matt Dillon began dating Cameron Diaz in 1995 after they met on the set of There's Something About Mary, in which they co-starred. Their on-screen chemistry translated into a real-life relationship, leading them to date for almost three years. Their relationship ended in 1998 but they both regard their time together fondly.

    Cameron Diaz is an esteemed American actress known for her roles in successful films such as Charlie's Angels and The Holiday. Her captivating performances and distinct allure have contributed to her lasting impact and fame in the film industry.

    • Age: 51
    • Birthplace: San Diego, California, USA