Why Winona Ryder Was Matt Damon’s Last A-List Relationship: Romance Rewind

Matt Damon and Winona Ryder, both talented and attractive, seemed perfect for each other. Their relationship was not as legendary as some of their films, yet both Ryder, now 52, and Damon, 54, fondly remember it. Let’s take a closer look at their story.

How it Began

Rewind to December 1997. Gwyneth Paltrow, before her Oscar win and GOOP fame, was dating Ben Affleck while being close friends with Ryder. Paltrow introduced Ryder to her friend Damon, Affleck's best friend. This moment turned awkward as Damon's Good Will Hunting co-star, Minnie Driver, thought they were still together.

A few weeks later, in January 1998, Damon declared himself "single" on a talk show, revealing their split. Driver expressed disappointment, stating, "It seemed like a good forum for him to announce to the world that we were no longer together." She added it was inappropriate, especially after he professed love for her on a show just weeks prior. Shortly after, he was seen publicly with Ryder, enjoying double dates with Paltrow and Affleck.

How Long it Lasted

Despite a rocky beginning, Ryder and Damon dated for two years. Their relationship was serious but not aimed at lasting forever. They ended things in early 2000, just before entering the new century.

How it Ended

This star-studded couple managed to maintain privacy around their relationship. They separated quietly in spring 2000, while Damon denied speculations of involvement with Penelope Cruz. Their mutual preference for privacy likely influenced their detachment from such a visible relationship. Damon later stated he intentionally chose to refrain from dating celebrities. He shared in an interview, "These days I only date, as we say, ‘civilians.’"

Damon also noted his hesitation toward celebrity relationships, emphasizing his desire for a normal lifestyle. He has since been with his wife, Luciana Barroso, a bartender, for over 20 years while raising their three children along with Barroso's son from her previous relationship.

What They Said About Each Other

Both Damon and Ryder approached their high-profile breakups cautiously. Ryder, promoting "Girl, Interrupted," stayed tight-lipped about Damon. He, in turn, evaded personal questions, often praising her acting talent instead.

What They Say Now

Ryder and Damon appeared to part on amicable terms and have remained supportive over the years. Following Ryder's 2001 shoplifting incident, Damon stood up for her. He mentioned, "To me it was like, ‘This too shall pass,’ because she’s a great woman."

He regarded their break-up as fair, obscurely referencing a humorous situation involving Richard Gere. Ryder honored Damon’s support, claiming in 2009 that he is "a greater, nicer guy." In a 2016 interview, she noted he provided valuable career guidance: "The less known about me, the better, because I just want people to think of me as the character." She credited Damon with this insight.

Key Relationship Takeaways

Damon and Ryder captured admiration, but they faced challenges as an A-list couple. It's evident they sought peace with less famous partners afterward. Ryder has been in a happy relationship with Loomstate founder Scott Mackinlay Hahn since 2010, saying, "He really is great. I’m really lucky."

Fans continue to hope for a movie reunion, perhaps without additional A-list distractions. Their brief yet notable romance remains fondly remembered in pop culture history.

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