Despite his high profile in Hollywood, Matt Damon has managed to keep a low profile when it comes to his love life. (He’s been happily married for 18 years.) But that wasn’t always the case—early in his career, the Bourne franchise star had an ugly breakup and a subsequent romance with two big stars, both of which made headlines. One of those relationships marked the actor’s vow to stop going out with other celebrities. Read on for a look back at Damon’s time dating Winona Ryder and why he says it made him want to “only date civilians” going forward.
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When Damon rose to fame with 1997’s Good Will Hunting, he was romantically involved with Driver, who he met through the film. But before he and Affleck won their Oscar, his relationship with his co-star was already over. Driver complained in a 1998 Los Angeles Times interview that Damon revealed their breakup publicly when he was on The Oprah Winfrey Show. By some accounts, that was how the Circle of Friends star learned they were over as well.
Damon was next linked to Ryder, who he met through Affleck’s then-girlfriend Gwyneth Paltrow. After making their initial rounds during the 1998 Oscar party circuit, the couple stayed together for over two years before parting ways in 2000. (Both kept the relationship and their breakup relatively private.) While there were rumors of a romance with his All the Pretty Horses co-star Penelope Cruz, Ryder was Damon’s last public relationship with another famous actor.
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In a 2004 Playboy interview, Damon gave some insight into why he moved away from high-profile love affairs after Ryder. He explained what it was like watching Affleck get dragged through the press and be portrayed as “trying to seek publicity” during his first try at love with now-wife Jennifer Lopez in the “Bennifer” days of the early 2000s.
“Ben got killed because he was in a high-profile relationship and the press [expletive] teed off on him,” Damon recalled, adding that despite the attention, “privately, you saw how much love was there.”
These experiences made Damon want to stay out of the tabloids. “If you’re the cover child or the cover couple, then you’re [expletive,” he opined to Playboy. And the easiest way to not land on the cover? “[D]on’t date a celebrity,” he continued, adding that this philosophy had enabled him to maintain a mundane life. “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. I compartmentalize.”
That same year he shared that his days of dating fellow actors like Driver and Ryder were over. “That was early on,” he told Australia’s The Age. “These days I definitely only date, as we say, ‘civilians.'”
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When he publicly made these remarks about staying out of the celebrity trenches, Damon was already dating a so-called “civilian”: former bartender Luciana Barroso. As Barroso recounted to Vogue Australia in 2018, Damon was filming 2003’s Stuck on You in South Beach, Miami when he and other members of the production landed in the bar where she worked. He ended up hiding out behind the bar with his future-wife when fans started getting “aggressive” asking for autographs.
“So I put him to work with me!” she recalled. “I said: ‘You know, if you’re going to be back here, you can’t just be standing there!’ He had trained as a bartender for a film years before, so he started making drinks. And he made me a ton of money in tips that night, because of course everyone wanted to go and see him. So it turned into a really fun night, and then 15 years later here we are!”
Damon’s non-famous dating strategy seems to have worked. The two are still together 20 years later and are now parents to four daughters, including Barroso’s child from a previous relationship.
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