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Who: Golden Globe-nominated actress Cameron Diaz, 47, and Oscar-nominated actor Matt Dillon, 56.
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). According to Diaz, via 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: 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: These two had the country club gala look down. The evening gown + 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: 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.”
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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 and Madden welcomed daughter Raddix in late 2019.
The actress hasn’t starred in a film since 2014, a decision she recently described as giving her “peace in my soul.”
Dillon has reportedly been dating actress Roberta Mastromichele for several years.
Next up, Dillon is set to star in political satire Land of Dreams alongside Minnie Driver.
#TBT: Check in every Thursday as we throw it back to some of our favorite celebrity couples of all time.