It was 1998. Damon was 28, devastatingly handsome, and had just won an Oscar for the Best Original Screenplay for Good Will Hunting. He and Ben Affleck had delivered one of the most charming speeches in Academy Award history. (He had also been nominated for an Oscar for Best Actor but lost to Jack Nicholson for his performance in As Good as It Gets.) He was dating his Hunting co-star Minnie Driver, who had also been nominated for an Oscar — for Best Supporting Actress — but lost to Kim Basinger. To label Damon and Driver as Hollywood’s “it” couple at that moment in time would be an understatement. They were basically untouchable.
Cue Oprah! Driver, then 27, and Damon had been dating for more than a year at that point, but when asked about his relationship status while appearing on an episode of The Oprah Winfrey Show, the actor said he was single. This was, apparently, news to his girlfriend (correction: ex-girlfriend). The British beauty told the Los Angeles Times how she felt about the way he’d ended their relationship, and while she clearly held her tongue, she also was obviously not very happy. “ It’s unfortunate that Matt went on Oprah,” she said. (Umm, yeah.) “It seemed like a good forum for him to announce to the world that we were no longer together, which I found fantastically inappropriate. Of course, he was busy declaring his love for me on David Letterman a month previously.” Honestly, “fantastically inappropriate” is pretty restrained if you ask us.
Damon went on to date Winona Ryder, whom he met through his BFF Ben Affleck’s then-girlfriend Gwyneth Paltrow. Ultimately, however, he married someone who was not a famous actress but a bartender in Miami Beach, Luciana Barroso. They’ve now been married for nearly 12 years and share four children (one of whom is Barroso’s from a previous relationship).
Driver’s romantic life has been less steady. Soon after the Damon split, she was linked with Harrison Ford, who was 28 years her senior. She was later engaged to Josh Brolin, but they broke up before making it down the aisle. And she also was pretty serious with magic man Criss Angel, until Cameron Diaz (or maybe Paris Hilton, depending on which reports you believe) stole him out from under her.
In 2008, Driver had a son named Henry after a brief relationship with a TV writer, and it’s clear her towheaded boy is the light of her life.
Years later, Driver doesn’t seem bitter about the way Damon cut her loose. She reflected on the incident again in 2011, explaining, “I was young for my age and didn’t have any of my family around me, so I was probably just a bit lost, and I upset a few people because there were times when I spoke before I thought,” she said. “You fall out with the wrong person and then you’re done for.”
At another point, she described what happened pretty succinctly: “I was young and I fell for him — it’s an occupational hazard.” Fair enough.
All’s well that ends well
Fast forward to the 2016 Emmys, where Damon exited the stage just before Driver entered. (He had been up there harassing his friend and Emmy host Jimmy Kimmel in a comedy bit; she was about to present an award.) While there were no formal reports that the former flames ran into each other, or even briefly passed in the halls, there was plenty of delight in the Twitterverse about the potential awkwardness of the situation.
The reality, however, is that they are both probably way more over their relationship — and breakup — than we are.
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