Matthew Perry's iconic character Chandler Bing was known for his romance with wife Monica Geller in Friends (Courteney Cox) — but what about the late star's real-life love stories?
Perry, who died on Saturday at age 54, detailed many of his relationships with high-profile stars in his 2022 memoir, Friends, Lovers and The Big Terrible Thing.
Although the actor never married, he was previously engaged to Molly Hurwitz. With his former flames, including Hurwitz and Gwyneth Paltrow, remembering Perry on social media, here's a look back at some of his romances.
Gwyneth Paltrow took to Instagram to reflect on her brief romance with Perry in 1993. Looking back, she fondly remembered their "magical summer" and kissing in the grass ahead of Perry's breakout role in Friends, which premiered in 1994.
"I met Matthew Perry in 1993 at the Williamstown Theater Festival in Massachusetts. We were both there for most of the summer doing plays. He was so funny and so sweet and so much fun to be with," she wrote. "He had shot the pilot of Friends but it had not aired yet. He was nervous, hoping his big break was just around the corner. It was. We stayed friends for a while until we drifted apart, but I was always happy to see him when I did. I am super sad today, as so many of us are. I hope Matthew is at peace at long last. I really do."
Perry's first big Hollywood romance was with Julia Roberts, whom he dated between 1995 and 1996.
Their relationship began after Friends producers approached the Pretty Woman star about a guest role in the show. She accepted on the condition that her storyline was with Chandler.
But the pressure of dating a big celebrity proved too much for Perry, who wrote in his memoir, "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? So instead of facing the inevitable agony of losing her, I broke up with the beautiful and brilliant Julia Roberts. 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."
In the early days of his Friends superstardom, Perry dated another star of one of TV's biggest hits, Baywatch's Yasmine Bleeth.
On Friends, Chandler often mentioned his crush on Bleeth during episodes of the sitcom, both before and after their fling.
One of Perry's most high-profile romances was with former fashion student Rachel Dunn, whom he dated from 2003 to 2005. The actor characterized Dunn as "the ex-girlfriend of his dream" in his memoir.
The two split around the time Friends ended.
"There was no drama involved [in the breakup], just a commitment by Matthew to stay focused on his sobriety," a source close to the former couple told People at the time.
Perry had a long relationship with Fleishman Is in Trouble star Lizzy Caplan, whom he dated for six years. They broke up in 2012.
Most of the details of their relationship emerged in Perry's book, where he wrote about regretting not asking Caplan to marry him.
"All my fears reared up like a snake," he wrote. "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."
Perry's final serious relationship was with literary agent Molly Hurwitz.
Perry and Hurwitz began dating in 2018, and in November 2020, the actor said he "decided to get engaged," telling People, "Luckily, I happened to be dating the greatest woman on the face of the planet at this time."
By 2021, the engagement was called off. In a statement about the split, Perry said, "Sometimes things just don't work out and this is one of them. I wish Molly the best."
Following the actor's death, Hurwitz revealed the impact their relationship had on her life.
"While I loved him deeper than I could comprehend, he was complicated, and he caused pain like I'd never known," she wrote on Instagram. "No one in my adult life has had a more profound impact on me than Matthew Langford Perry. I have tremendous gratitude for that, for everything I learned from our relationship."