In the late '90s, amidst other high-profile celebrity couples, Matt Damon and Winona Ryder quietly dated for nearly two years, keeping their romance under the radar. The relationship followed Damon's public breakup with his Good Will Hunting co-star Minnie Driver. The two actors parted ways in 2000 after a brief romance, with Damon then deciding to avoid dating celebrities.
Legend has it that Gwyneth Paltrow, then dating Damon's best friend Ben Affleck, introduced Damon and Ryder. Despite multiple sightings and paparazzi photos, the couple kept details of their relationship private. After making a public appearance together at the Golden Globes in 2000, Damon and Ryder went their separate ways.
In a 2004 interview, Damon mentioned that he now exclusively dated "civilians," expressing a preference for a normal lifestyle that dating non-celebrities allowed. He emphasized that falling in love with a celebrity would mean changing his lifestyle, and he valued the sense of normalcy in his life.
Damon elaborated on his aversion to dating celebrities in an interview with Playboy, stating that the celebrity lifestyle magnified aspects he didn't like, interfering with both his personal life and his work. He emphasized that maintaining a normal lifestyle was crucial to him.
Shortly after these revelations, Damon met and married Luciana Barroso. The couple has been married for 18 years and has four daughters. On the other hand, Winona Ryder has been in a steady relationship with fashion designer Scott Mackinlay Hahn since 2011.
Recent discussions about Damon's romance with Ryder were sparked by comments made by his ex, Minnie Driver, on Instagram. A fan page posted a clip from the 1998 Oscars, showing Damon and Affleck winning for Good Will Hunting. Driver's comment revealed that Damon had ended their relationship a few weeks before the event and attended the Oscars with his new girlfriend, leaving her devastated.
