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A Pretty Woman and a favorite Friend! Matthew Perry and Julia Roberts briefly — and secretly! — dated in the mid-‘90s, the actor revealed in his October 2022 memoir, Friends, Lovers and the Big Terrible Thing.
The actors’ short-lived romance began in 1995, when Perry — per Roberts’ ultimatum — convinced the Sleeping With the Enemy star to appear in a season 2 episode of the NBC hit.
“Julia had been offered the post-Super Bowl episode in season 2 and she would only do the show if she could be in my story line,” the 17 Again star penned in his memoir, per the U.K.’s The Times. “Let me say that again — she would only do the show if she could be in my story line. (Was I having a good year or what?)” he quipped. “But first, I had to woo her.”
As for how the Fools Rush In actor persuaded the Oscar winner to take the role in “The One After the Super Bowl,” he had to invoke some real brain power.
After sending Roberts three dozen roses with a note expressing his excitement at the possibility of her guest-starring on the series, “Her reply was that if I adequately explained quantum physics to her,” she’d agree to be on the show,” Perry wrote. “The following day, I sent her a paper all about wave-particle duality and the uncertainty principle and entanglement, and only some of it was metaphorical.”
Though they were an item by the time Roberts filmed the fan-favorite Friends episode in 1996, Perry — who got candid about his struggles with mental health issues and substance abuse in his memoir — broke it off shortly after. “Dating Julia Roberts had been too much for me. I had been constantly certain that she was going to break up with me,” he wrote in his memoir. “Why would she not? I was not enough; I could never be enough; I was broken, bent, unlovable. So instead of facing the inevitable agony of losing her, I broke up with the beautiful and brilliant Julia Roberts.”
The West Wing alum — who said he became convinced the Steel Magnolias star had been “slumming it” with him — added, “I can’t begin to describe the look of confusion on her face.”
After his split from Roberts, Perry went on to date several more high-profile stars, including Mean Girls actress Lizzy Caplan and Gilmore Girls alum Lauren Graham. He got engaged to Molly Hurwitz in November 2020, but the two called it off six months later. “Sometimes things just don’t work out and this is one of them,” the actor’s rep told Us Weekly in June 2021. “I wish Molly the best.”
Roberts, for her part, married Danny Moder in 2002. They welcomed twins Hazel and Phinneaus two years later, followed by son Henry in 2007.
Keep scrolling to relive Perry and Roberts’ ‘90s-stolgic romance:
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