Both easy on the eye and regarded as two of the biggest talents of their generation, Matt Damon and Winona Ryder seemed like a match made in Hollywood heaven. While their relationship wasn’t as epic as some of their movies, it seems that both Ryder, now 52, and Damon, 54, look back on it fondly — so now it’s time for Us to do the same…
How it Began
Cast your mind back to December 1997 (if you were born!): Gwyneth Paltrow, not yet an Oscar winner nor the queen of GOOP, was dating Ben Affleck, and was also great friends with Ryder. Paltrow introduced her friend to Affleck’s BFF Damon and… well, this is where it all gets a little awkward because his Good Will Hunting costar Minnie Driver thought she was still dating him at the time.
It was only when Damon described himself as “single” on a talk show a few weeks later, in January 1998, that Driver realized they had, in fact, split. “It’s unfortunate that Matt went on [the show],” Driver told The L.A Times later that year. “It seemed like a good forum for him to announce to the world that we were no longer together, which I found fantastically inappropriate. Of course, he was busy declaring his love for me on David Letterman a month previously.”
Sure enough, he was soon publicly stepping out with Ryder across the spring awards season, and enjoying double dates with Paltrow and Affleck. Look, these guys were all in their mid-twenties at the time; things get messy, we forgive them (let’s hope Driver does too?).
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How Long it Lasted
Despite their slightly complicated start, they ended up dating for two years: serious, but not “together forever” serious. They just made it into the 21st century before splitting early in 2000.
How it Ended
This seriously A-list couple somehow managed to keep the juicy details of their relationship pretty private, splitting quietly in spring 2000, with Damon denying rumors that he was involved with Penelope Cruz.
Their shared love of privacy might also be why, ultimately, both moved on from such a high-profile pairing. In fact, Damon has openly admitted that, post-Ryder, he made a conscious choice to stop dating famous people. “These days I definitely only date, as we say, ‘civilians,’” he said in an interview with Sunday magazine in 2004.
Around the same he told Playboy, “I don’t think I could fall in love with a celebrity right now, because it would mean changing my lifestyle, and I like that my lifestyle feels normal to me most of the time.”
Sure enough, he’s now been with his wife Luciana Barroso, a bartender, for more than 20 years and the pair have raised three children together, along with Barroso’s son from a previous relationship.
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What They Said About Each Other
Both burned by their high-profile previous romances — Damon’s aforementioned awkward breakup from Driver, and Ryder’s notoriously passionate 1989-1993 relationship with Johnny Depp — they clearly had a policy of not talking about each other in public while they were together.
While promoting Girl Interrupted around the world throughout 1999, Ryder was tight-lipped about her boyfriend, while Damon would also cagily dodge questions about his love throughout their relationship, usually just praising her acting skills instead.
What They Say Now
These two clearly had an amicable split: they’ve been very kind about each other in the years since. When Ryder hit headlines for her 2001 shoplifting incident, Damon jumped to her defense. “When she was being pilloried in the press, to me it was like, ‘This too shall pass’,” he told Playboy. “That somehow her true colors would come out and she would get past it because she’s a great woman.”
In the same interview, he said their split was low on drama. “It ended for reasons far more pedestrian than, say, a mad orgy at the Four Seasons during which my feelings were hurt because Richard Gere was too interested in her,” he said, nodding to her 2000 movie with Gere, Autumn in New York.
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Ryder clearly appreciated the support from her ex, telling Black Book in 2009: “Matt couldn’t be a greater, nicer guy. I’m really lucky that I’m on good terms with him.” In a 2016 chat with Interview magazine, she also quoted Damon as a source of career wisdom. “There are actors I know personally, or I’ve heard them say, ‘The less known about me, the better, because I just want people to think of me as the character’,” she said. “I think Matt Damon said that recently. He has a point and I think I get that.”
Key Relationship Takeaways
These two were cute together, but ultimately way too A-list to stay together — for their own sanity! It’s no surprise that they have both subsequently found happiness with people considerably less famous — Ryder has been quietly dating Loomstate clothing founder Scott Mackinlay Hahn since 2010. “He’s so great,” she told Harper’s Bazaar in 2024. “He really is. I’m really lucky.”
Our one wish for the briefly incredible couple that was Ryder and Damon? That, one day, they might appear in a movie together (but probably not one also starring Minnie or Gwynnie…).
