At the turn of the millennium, Matt Damon and Winona Ryder were one great, and seriously A-list, couple, so let’s look back at their relationship
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.
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 .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.
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.” 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.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.
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