Matthew Perry dated many A-listers during his decades of fame before his death at age 54.
Matthew Perry was in a number of high-profile relationships before his tragic death on October 28 at age 54. The Friends actor became one of the biggest names in Hollywood thanks to his role as Chandler Bing on the sitcom from 1994 to 2004, and he was linked to many A-list women, including Julia Roberts, Valerie Bertinelli, Lizzy Caplan, and more.
Keep reading to learn about his love life before his sudden passing.
The 17 Again actor appeared to be single at the time of his death. He was reportedly found dead from an apparent drowning in a jacuzzi at his Los Angeles home, according to TMZ.
His last public relationship was with literary agent Molly Hurwitz. The pair began dating in 2018 and even got engaged in 2020 before ultimately calling it quits one year later.
“Sometimes things just don’t work out and this is one of them. I wish Molly the best,” Matthew said in a statement to People in June 2021.
Matthew was never married, and Molly was the only girlfriend he was ever publicly engaged to.
His longest relationship was with Mean Girls actress Lizzy Caplan. The pair broke up in 2012 after six years together, and Matthew said in his 2022 memoir, Friends, Lovers, and the Big Terrible Thing, that they almost got engaged during their time together.
“All my fears reared up like a snake,” he wrote about their breakup. “I often think if I’d asked [her to marry me], now we’d have two kids and a house. Instead, I’m some schmuck who’s alone in his house at 53.”
Perhaps his most famous love affair was with Julia Roberts. They dated for a few months in 1996 and were a real life couple when she appeared on season 2 of Friends. Matthew ultimately ended their relationship, which he detailed in his book.
“Dating Julia Roberts had been too much for me. I had been constantly certain that she was going to break up with me. Why would she not? I was not enough; I could never be enough; I was broken, bent, unlovable,” he wrote. “So instead of facing the inevitable agony of losing her, I broke up with the beautiful and brilliant Julia Roberts.”
He joked, “She might have considered herself slumming it with a TV guy, and TV guy was now breaking up with her. I can’t begin to describe the look of confusion on her face.”
Matthew did not have any children, but he talked fondly about the idea of having a family before his death.
He told People in October 2022 that he thought he would make a “great” dad, adding, “I grew up with a lot of little kids around me, and that’s probably why, but I can’t wait.”
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