The Canadian actor stepped into the spotlight with his role younger brother of Valerie Bertinelli's title character on the 1990 show Sydney, but it wasn't until he landed the role of Chandler Bing on Friends in 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.
Michael Kovac/FilmMagic Matthew Perry
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."
From Bober to Julia Roberts to Molly Hurwitz and everyone in between, here's a look at Perry's dating history through the years.
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"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 the Friends actor revealed that he had deep feelings for his former Sydney costar, the two never officially dated.
Perry began dating Tricia Fisher, the half-sister of the late Carrie Fisher, around the time A Night in the Life of Jimmy Reardon wrapped 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, while Friends was at its peak," Perry noted. "She didn't abandon me, but old fears crept up, and I ended the relationship."
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In his memoir, Perry opens up about a handful of former flings, including Gwyneth Paltrow, describing their brief "make-out session in a closet" the summer before Friends was broadcast in 1994.
When the topic arose during an interview with GQ, 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."
nbc Matthew Perry and Julia Roberts
Julia Roberts marked Perry's first high-profile girlfriend, a relationship that began while shooting an episode of Friends. In his memoir, the actor told the story of how Roberts signed up to guest star on the hit sitcom, noting that she was eager to be part of his character's storyline.
Perry said that he went to New Mexico to ring in 1996 with her and met her family. "I did let her in, both figuratively and literally, and a relationship began," the actor wrote. "We would already be a couple by the time we started filming the Friends Super Bowl episode."
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."
In his memoir, Perry briefly opened up about his relationship with Veep producer Gabrielle Allan, who he referred to as Gaby, while discussing a time in his life when he realized alcohol really started to control him.
"Love of alcohol had indeed become the helmsman of my life, but I don't think I realized just how much it controlled me until one night when I was out with my girlfriend at the time, Gaby," he writes, adding that she would "go on to write for Veep and a bunch of other stuff and be a friend for life."
He recalled one instance when he "first felt the obsession for alcohol" after the then-couple went to a magic show in University City and returned to Gaby's house.
"Gaby didn't have any alcohol at home, which is, of course, totally fine, but for me at the age of twenty-one, all of a sudden this creeping feeling came over me for the first time. I felt my blood on fire for more to drink."
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In his memoir, Perry detailed his past romance with the late Jamie Tarses. He met her in 1994, prior to being cast in Friends, and dated her for several years after she divorced her then-husband, Fox TV producer Dan McDermott.
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.
"I need time to process being sober," Perry recalled telling her at the time of their breakup. "In order to adequately pay sweet Jamie back for two years of giving up huge portions of her own very busy and important life by basically being my nurse, I ended our relationship."
The two ended things around the time Friends wrapped. "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.
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.
Perry detailed an incident that occurred with Cameron Diaz at a group dinner after being "set up" with the actress shortly after her 2007 breakup with Justin Timberlake. He recalled Diaz "accidentally" hitting his face while aiming for his shoulder after he said "something witty" following a game of Pictionary.
Perry's longest relationship was with Mean Girls alum Lizzy Caplan, though they kept their relationship fairly quiet when they were dating. Though he doesn't mention Caplan by name in his memoir, he mentioned that their romance began as "friends with benefits." After six years together — and almost getting engaged — the couple separated in 2012.
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."
getty; Matthew Perry/instagram Matthew Perry and Molly Hurwitz
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 dating the greatest woman on the face of the planet at this time."
Despite Perry's fame, the two kept a low-profile relationship. Hurwitz posted a sweet tribute on her private Instagram page in 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 out and this is one of them," Perry said in a statement to PEOPLE. "I wish Molly the best."