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Before actor Matt Damon got married and became a father of four, he was one of the most sought-after celebrity bachelors. In 1997, he won an Academy Award for Best Screenplay for Good Will Huntingco-written with longtime friend Ben Affleck. The critically acclaimed movie launched Damon’s career as one of the most successful actors in Hollywood. Minnie Driver also appeared in the film, earning an Oscar nomination for her role as Skylar, the love interest of Will, played by Damon.

The two stars, who shared a brief off-screen romance during that time, experienced a bitter breakup. Promoting her new memoir, Managing Expectations, Minnie Driver recently said the split with the Oscar-winning actor was “agony.”

Minnie Driver and Matt Damon had a whirlwind romance

Minnie Driver Matt Damon Good Will Hunting
Matt Damon and Minnie Driver in 1997 | Frank Trapper/Corbis via Getty Images

In an interview with Entertainment Tonight, Driver revealed that her whirlwind romance with the Bourne Identity star was “sweet,” but it was over before Good Will Hunting hit the awards show circuit.

The actor said her family had predicted the breakup. “They could see that this young man was rocketing really fast and so was I. And when you’re young, it’s pretty hard to keep your head on straight and to maintain a grounded sense of deportment.” She said her family told her: “‘This may well end badly for reasons that are to do with all these things coming together in a perfect storm.'”

Her family was right.

After less than a year of dating, Damon appeared on The Oprah Winfrey Show declaring he was single — unbeknownst to Driver, who found out with the rest of the world. She was devastated. The Phantom of the Opera star claimed the public breakup was in all the tabloids, and she had to face the photos every time she walked into a supermarket.

Driver, who once referred to celebrity relationships as “an occupational hazard,” said, “I don’t care who you are — that is agony, and it’s like a strange, surreal dream.”

The actor now reflects on her time with Damon, saying it was “a sweet romance that was just a sweet love affair in the center of all of that stuff but had a combustible ending, which then became the focus.”

Minnie Driver has a thing or 2 to say about Matt Damon

Driver told Entertainment Tonight that her father helped her get through the emotional public breakup with Damon, “‘You’re not going to want to hear this, but the best thing I can tell you is, you’re definitely going to feel this way about somebody else.,'” Driver recalls her dad saying. “He was so right!”

Once the Oscars were over, the couple parted ways and formed new relationships. Not until 2017 did the two actors appear in the headlines again, but this time for a very different reason.

At the height of the #MeToo movement, Harvey Weinstein, who had produced Good Will Hunting, was embroiled in scandal. Matt Damon took to Twitter, referring to the situation as a “culture of outrage and injury.” Driver replied, “Good god, seriously?” and claimed the Talented Mr. Ripley actor was “systemically part of the problem,” the Independent reported.

Driver revealed in a September 2021 podcast episode of Keep It! that she ran into Damon and his family on the beach the previous summer. “I feel so much of the folly of youth went on with our initial relationship, like it was amazing and tabloidy,” she said. “So that was nice to just have sort of a middle-aged conversation about the weather and stuff.”

The ‘Good Will Hunting’ star is happily married

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‘Good Will Hunting’: Matt Damon and Minnie Driver’s ‘Horrendous Breakup’ Made 1998 ‘Pretty Bizarre’

The Saving Private Ryan actor has been married to Luciana Barroso since 2005. According to Parade, the couple met in 2003 while she was a single mother bartending in Miami. They had an instant connection and have been inseparable ever since.

Barroso’s daughter from a former relationship, Alexia, is now 23 years old. Damon and his wife share three daughters, Isabella (15), Gia (13), and Stella (11). 

Driver has not been married but was engaged briefly to actor Josh Brolin in 2001. The Grosse Pointe Blank actor shares a 13-year-old son, Henry, with film producer Timothy J. Lea. She has been in a relationship with filmmaker Addison O’Dea since 2019.