Matt Damon and Minnie Driver fell in love while the rest of the world was going gaga over their surprise 1997 hit, Good Will Hunting. But while Matt’s character chases after Minnie at the end of that mushy flick, their actual affair ended awkwardly and abruptly when he denied having a girlfriend during an appearance on The Oprah Winfrey Show.
After her man confessed in front of millions that their relationship was amicably over (and had been for a couple of weeks), Minnie milked her newfound rep as the woman scorned, referencing Damon’s dumping in interviews and telling The Los Angeles Times, “It’s unfortunate that Matt went on Oprah. It seemed like a good forum for him to announce to the world that we were no longer together, which I found fantastically inappropriate.”
Even less appropriate was Matt jumping in bed with Winona “Sticky Fingers” Ryder just weeks later. Will Hunting may have been good, but the guy who played him was a straight-up bad boy.