Winona Ryder and Matt Damon Reflect on Their 1990s Romance

LOS ANGELES, Calif. — Winona Ryder and Matt Damon, two of Hollywood’s most iconic stars of the 1990s, recently reflected on their brief but memorable romance that captivated fans during the height of their careers. The pair, who dated from 1998 to 2000, have remained on good terms, with both speaking fondly of their time together in recent interviews.

The relationship began after Ryder was introduced to Damon by mutual friend Gwyneth Paltrow, who was dating Damon’s close friend Ben Affleck at the time. Their connection blossomed during the spring awards season of 1998, where they were frequently spotted together at high-profile events. However, their romance was not without its complications. Damon had recently ended a relationship with actress Minnie Driver, which had ended awkwardly after he publicly declared himself single on a talk show.

“It’s unfortunate that Matt went on [the show],” Driver told The Los Angeles Times in 1998. “It seemed like a good forum for him to announce to the world that we were no longer together, which I found fantastically inappropriate.” Despite the rocky start, Damon and Ryder’s relationship quickly became a media sensation, with the pair often seen enjoying double dates with Paltrow and Affleck.

Ryder, now 52, and Damon, 54, have both moved on from their high-profile romance. Damon has been married to Luciana Barroso since 2005, and the couple has three children together. Ryder, meanwhile, has been in a long-term relationship with Scott Mackinlay Hahn since 2010. Both actors have spoken about the challenges of dating within the entertainment industry and the importance of maintaining privacy.

“These days I definitely only date, as we say, ‘civilians,'” Damon told Sunday magazine in 2004. “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.”

Despite their split, Damon and Ryder have remained supportive of each other. When Ryder faced public scrutiny during her 2001 shoplifting incident, Damon was quick to defend her. “When she was being pilloried in the press, to me it was like, ‘This too shall pass,'” he told Playboy. “She’s a great woman.”

Ryder has also expressed gratitude for Damon’s support over the years. “Matt couldn’t be a greater, nicer guy,” she told Black Book in 2009. “I’m really lucky that I’m on good terms with him.” In a 2016 interview, she even credited Damon with influencing her approach to her career, quoting his belief that “the less known about me, the better, because I just want people to think of me as the character.”

While their relationship may have been short-lived, Ryder and Damon’s time together remains a fascinating chapter in Hollywood history. Both have since found happiness outside the spotlight, but their brief romance continues to intrigue fans of 1990s cinema.