Matthew Perry's Dating History: From Gwyneth Paltrow to Molly Hurwitz

Photo: Michael Kovac/FilmMagic

Matthew Perrywas linked to some big names in Hollywood.

TheCanadian actor stepped into the spotlight with his role younger brother ofValerie Bertinelli’s title character on the 1990 showSydney, but it wasn’t untilhe landed the role of Chandler BingonFriendsin 1994 that he shot to fame.

Over the course of his 30-plus years in the entertainment industry, Perry explored several romantic relationships, including high-profile ones such as Julia Roberts and Cameron Diaz.

Concurrently, the actor endureda tumultuous time in the spotlight. Upon being cast inFriends,his alcohol addiction startedto surface, which Perry detailed in his 2022 memoir,Friends, Lovers and the Big Terrible Thing.

While he noted that among those lows were the relationships he lost due to his addiction, he thanked a number of his past lovers for saving his life — such as his first girlfriend Gabrielle Bober, “the one who pointed out that something was wrong with me and sent me to rehab for the first time.”

In October 2023,Perry was found deadat a Los Angeles-area homeTMZreported, citing law enforcement sources. Law enforcement sources also confirmed Perry’s death to theLos Angeles Times. The outlet reported that Perry was found in a jacuzzi at the home, and no drugs were found at the scene.

A spokesperson for the Los Angeles Police Department told PEOPLE that officers responded to a call at Perry’s address regarding the death of a male in his 50s, but would not confirm the deceased’s identity.

Ahead, look back at Perry’s past relationships and what he had said about them through the years.

Valerie Bertinelli

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Perry reveals in his memoir that he hada secret make-out session with Bertinelliwhile her then-husband, the lateEddie Van Halen, was passed out a few feet away.

“Valerie and I had a long, elaborate make-out session. It was happening — maybe she felt the same way I did. I told her I had thought about doing that for a long time, and she had said it right back to me.”

While theFriendsactor revealed that he had deep feelings for his formerSydney costar, the two never officially dated.

Tricia Fisher

Perry began datingTricia Fisher, the half-sister of the late Carrie Fisher, around the timeA Night in the Lifeof Jimmy Reardonwrapped filming. He was 18 years old at the time.

He detailed the lengths to which his relationship with her deepened, noting that things went emotional to physical very quickly. Despite her desire to take their romance to the next level, Perry recalled his decision to wait.

“My firmness, at least in my conviction to wait, lasted two months… The make-out sessions that didn’t lead anywhere were beginning to cause both of us to hyperventilate,” he wrote — so Tricia made the first move and took him to his bed.

Though they split for some time, they reconnected again later in life. “Years later, Tricia and I would date again, whileFriendswas at its peak,” Perry noted. “She didn’t abandon me, but old fears crept up, and I ended the relationship.”

Gwyneth Paltrow

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In his memoir, Perry opens up about a handful of former flings, includingGwyneth Paltrow, describing their brief “make-out session in a closet” the summer beforeFriendswas broadcast in 1994.

When the topic arose during an interview withGQ, Perry considered what the actress might think of the published excerpt. “Hopefully, she’ll find it to be a cute story,” he said. “It’d be bad if Gwyneth Paltrow hated me; I wouldn’t like that.”

Julia Roberts

Matthew Perry and Julia Roberts.nbc

Julia RobertsmarkedPerry’s first high-profile girlfriend, a relationship that began while shooting an episode ofFriends. In his memoir,the actor told the story of how Roberts signed upto guest star on the hit sitcom, noting that she was eager to be part of his character’s storyline.

The two dated for a few months before Perry called it quits, much to Roberts' surprise.

“Two months later, I was single,” Perry wrote. “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, unloveable.”

Gabrielle Allan

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Jamie Tarses

Greg Doherty/Patrick McMullan via Getty

This was a relationship he valued, describing her as “the most magical, beautiful, and smart” woman. He added that she was there for him during his substance abuse struggles, which in part led to his decision to end things.

Rachel Dunn

Gregg DeGuire/WireImage

Perry dated former fashion student and longtime girlfriend Rachel Dunn for two years before breaking up in 2005. In his memoir, he described her as “the ex-girlfriend of his dream.”

Natasha Wagner

In his memoir, Perry referenced his relationship with Natasha Wagner, the daughter of Natalie Wood and Richard Gregson. Not only did he describe her as “beautiful, smart, caring and sexy,” but he said, “she had it all; she was perfect!”

But because he needed more and hadn’t “dated her properly,” the two parted ways, though they remain friends.

Cameron Diaz

Jon Kopaloff/FilmMagic

Perry detailed an incident that occurred withCameron Diazat a group dinner after being “set up” with the actress shortly after her 2007 breakup withJustin Timberlake. He recalled Diaz “accidentally” hitting his face while aiming for his shoulder after he said “something witty” following a game of Pictionary.

Lizzy Caplan

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He wrote that their breakup still haunts him to this day. “All my fears reared up like a snake,” he penned. “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 fifty-three.”

Molly Hurwitz

Matthew Perry and Molly Hurwitz.getty; Matthew Perry/instagram

Perry began dating literary manager Molly Hurwitz in 2018 and asked her to marry him in November 2020. “I decided to get engaged,” Perry told PEOPLE at the time. “Luckily, I happened to be datingthe greatest woman on the face of the planetat this time.”

Despite Perry’s fame, the two kept a low-profile relationship.Hurwitz posted a sweet tribute on her private Instagram pagein honor of Valentine’s Day in 2020. “Second year being my valentine, but his first as an Instagram influencer,” she wrote in reference to the actor’s massive following. “HVD to my favorite.”

Six months after, the actor popped the question while at a Switzerland rehab; however, the two called it quits for good in June 2021. “Sometimes things just don’t work outand this is one of them,” Perry said in a statement to PEOPLE. “I wish Molly the best.”

A few days after Perry’s death on Oct. 28, Hurwitzspoke out about their time togetherin a post onInstagram. She captioned a photo of Perry’s silhouette against a European city scape and opened up about the impact their relationship had on her life.

“He would love that the world is talking about how talented he was. And he really was very talented,” she began. “As the Friends reunion was approaching, we rewatched the show together.”

“‘F—, I was so good!!!’” she recalled him saying. “‘See what I did there???’”

Hurwitz gushed, “We rewound and studied scenes. Our respect and appreciation of humor is something that connected us. Being with him as he rediscovered his brilliance was magical.”

Elsewhere in the caption, she wrote: “While I loved him deeper than I could comprehend, he was complicated, and he caused pain like I’d never known,” she wrote. “No one in my adult life has had a more profound impact on me than Matthew Langford Perry."

She continued in part: “I have tremendous gratitude for that, for everything I learned from our relationship.”

source: people.com