Cameron Diaz and Matt Dillon Relationship

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.

Who

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”).

Alexander Ross

Alexander Ross

Gaming, Esports & Interactive Media Writer

Alexander Ross has covered the video game industry for a decade, writing deep dives on game design, esports tournaments, VR developments, and gaming culture.

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