Blast From The Past: Former Celebrity Couples

Winona and Matt, sitting in a tree…


In 1997, Matt Damon and Winona Ryder were introduced by Winona’s good friend, Gwyneth Paltrow who was at the time, dating Damon’s BFF Ben Affleck. Ok, got that straight? Supposedly the two gal pals later had a falling out over Gwyneth winning the Oscar for Shakespeare in Love, a part that Winona was originally offered first. Damon and Ryder also split in 2000, though both have had only good things to say about the other.

A very public breakup for Driver and Damon


In 1998 a 28-year-old Matt Damon went on Oprah after winning the Oscar for Good Will Hunting, and told the audience, and the world, that he was single. The truth, however, is that he wasn’t until the moment he said that. He had previously been dating his British costar Minnie Driver, and the actress only learned of her breakup on television. “It’s unfortunate that Matt went on Oprah,” Driver said. (You could say that!) “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.” “Fantastically inapporpriate” may not quite be the words we would have chosen but we appreciate the starlet’s restraint.