Back in 1998, Matt Damon was a Hollywood heartthrob. At only 28, he found himself with a hit film on his hands. “Good Will Hunting,” written with his bromance partner Ben Affleck, was a resounding success, gaining him Oscar buzz for his performance alongside film legend Robin Williams. Damon’s personal life seemed to be flourishing too. He met Minnie Driver on the set of the film and the two quickly hit it off, per Yahoo! News. The couple was frequently spotted together, and the two were so cute it seemed like they may have even been the real deal. But after a more than a year of dating, Damon had other plans.

Appearing on the “Oprah Winfrey Show,” Damon declared that he was single — harsh news for Driver, who Damon reportedly hadn’t bothered to tell in advance of the television appearance. Instead of dealing with their impending breakup in private, Damon aired the couple’s dirty laundry on a national stage and their split became one of the most talked-about celebrity breakups of its time. Driver shunned Damon, and the two didn’t even talk for over 20 years, per People. She recently told the magazine that her life has since been “messy, odd, and lovely.” Driver seemed content with never speaking to Damon again, but earlier this year, all of that changed.

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