Matt Dillon Said Cameron Diaz Was His "Muse"

"I fell in love. It’s a very powerful thing when you feel that way about somebody."

Smiling Cameron Diaz and Matt Dillon as a couple
Photo: Steve Granitz/Getty Images

Sure, she might have taken on the title of Mrs. Good Charlotte in 2015, but once upon a time (read: the '90s), Cameron Diaz played girlfriend and muse to Matt Dillon. And unlike some other Hollywood love stories that end in feuding and fanfare, this ex-couple didn't like drama — or the limelight for that matter. What they did like? Affectionate hand-holding, coordinated country club attire, and pulling at our heartstrings.

Keep scrolling for Cameron Diaz and Matt Dillon's complete relationship timeline.


Golden Globe-nominated actress Cameron Diaz, 50, and Oscar-nominated actor Matt Dillon, 58.

How They Met

The actors met in 1995 while they were shooting respective films in Minnesota (Feeling Minnesota for Diaz and Beautiful Girls for Dillon). As reported by Rolling Stone, the two didn’t begin dating until January of 1996 (though at the time she played coy regarding the name of her “boyfriend,” who she noted was “in the business”).

Why We Loved Them

Cameron Diaz in a black tube top and Matt Dillon with a black shirt and white undershirt holding hands

Gotta love love! Though Diaz and Dillon kept things low-key in the public eye, the few quotes the former did allow about her S.O. were endearing as hell. In ’97 Diaz told the British Guardian, “I love him incredibly.” According to Rolling Stone, the Charlie’s Angels star also once gushed about the actor’s work ethic: “Matty, he’s the best. He’s one of a kind … He’s never taken that commercial route. He’s an intelligent, poetic, full, real human being. And he’s down-to-earth. Matt is the greatest.” Quite the endorsement!

The pair went on to work together on There’s Something About Mary. Co-star Lin Shaye described their sweet behavior on set in ‘98, telling People, “Matt would come over and rub her shoulders … if it had been a long day. I would notice them sitting on a bench together, or stretching out with her head on his chest. They were affectionate in a really gentle way.”

When They Peaked

Cameron Diaz with a pixie alongside Matt Dillon in formalwear
Magma Agency/WireImage

These two had the country club gala look down. The evening gown and shoulder-wrapped cardigan style didn’t really make its way into the 21st century, but that’s OK — it died a happy, sartorially fulfilled death right then and there. Has a photo ever better encapsulated 1997?

The Breakup

Cameron Diaz with a pixie and nude turtleneck hugging Matt Dillon
Dave Benett/Getty Images

Reports cite the end of Diaz and Dillon’s relationship in ’98, following the release of There’s Something About Mary. Dillon opened up about the relationship years later, telling Parade in 2006, "I fell in love. It’s a very powerful thing when you feel that way about somebody. Cameron was a muse for me. I hadn't been in any deep emotional relationships.”

As for the split, he told Rolling Stone it was a matter of geography (sort of), explaining, “Look, I loved her and we were very close, but it just ran its course. We’re both actors, she was living in L.A., and I was living in New York, and I didn’t want to commit to moving out there. But I don’t want to say it was about any of those things. It just ran its course.”

Diaz has, for the most part, avoided commenting on her splits. When pressed by Andy Cohen to discuss her dating history in 2016, Diaz said, “You know what? Nothing matters now that I have my husband. I don’t even remember any of that,” referring to Benji Madden, whom she wed in 2015. “No one compares. Everything else just washes and slips away. You realize, ‘Oh, right, this is what the real thing is. This is what real love is. This is what real commitment and devotion is.’”

Where They Are Now

Diaz hasn’t starred in a film since 2014, a decision she described as giving her “peace in my soul.” However, after embracing motherhood and entrepreneurship — she welcomed daughter Raddix in late 2019, as well as started her own wine brand, Avaline, with business partner, Katherine Power — Diaz is ready to get back in the Hollywood saddle. She will be co-starring in the Netflix action-comedy Back in Action alongside Jamie Foxx.

Dillon has reportedly been dating Italian actress Roberta Mastromichele since 2014. He's been in a number of films in recent years and is set to co-star in the upcoming Wes Anderson rom-com drama, Asteroid City, in 2023.

#TBT: Check in every Thursday as we throw it back to some of our favorite celebrity couples of all time.

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