Breaking up is hard to do — maybe that’s why Matt Damon decided to cut ties with Minnie Driver by announcing their separation on national TV, instead of telling her directly… and in private.

The incident

View photos At the Good Will Hunting premiere on Dec. 2, 1997, Minnie Driver and Matt Damon only had eyes for each other. (Photo: AP Photo/John Hayes) More

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.

Moving on

View photos Matt Damon and wife Luciana Barroso have had 12 great years together. (Photo: Jordan Strauss/Invision/AP) More

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).

View photos Minnie Driver and Josh Brolin never quite made it down the aisle. (Photo: AP Photo/Rene Macura) More