Getty Matthew Perry with Rachel Dunn and Julia Roberts
“Friends” star Matthew Perry, who died at age 54 after an apparent drowning on October 28, 2023, was never married. However, he had a string of girlfriends over the years, and his dating history includes several prominent actresses.
Perry was found deceased in a jacuzzi of an apparent drowning after playing pickleball. TMZ first broke the story.
Perry went through highly publicized battles with substance abuse throughout his life.
Here’s what you need to know about Matthew Perry’s dating and girlfriend history:
Matthew Perry Broke Off an Engagement to Molly Hurwitz in 2021
Meet the late Matthew Perry’s ex-fiancée Molly Hurwitz
According to People Magazine, Perry broke off his engagement to literary manager Molly Hurwitz in 2021; she was his fiancee since November 2020.
“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.”
There was a big age gap. People reported that Perry was then 51, and Hurwitz was 29, and said they were together since 2018.
When Perry became engaged to Hurwitz, he told People, “I decided to get engaged. Luckily, I happened to be dating the greatest woman on the face of the planet at this time.”
Perry wrote in his book that he was high at the time of the proposal to Hurwitz, according to USA Today.
“I bought her a ring because I was desperate that she would leave me. I didn’t want to be this injured and alone during Covid,” he wrote. “I was high on 1,800 milligrams of hydrocodone when I asked her to marry me. I had even asked for her family’s blessing. Then I’d proposed, high as a kite. And on one knee. And she knew it too. And she said yes.”
Matthew Perry Almost Proposed to ‘Mean Girls’ Actress Lizzy Caplan But His ‘Fears Reared Up Like a Snake’
Lizzy Caplan, Zachary Quinto, Edie Falco, Stephen Lang and Rebecca Damon on the SAG-AFTRA picket line in NYC today #SAGAFTRAStrong
View the full gallery here: t.co/XiWC5SEUiz
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Perry almost proposed to “Mean Girls” star Lizzy Caplan, according to Hello Magazine.
The magazine reported that, according to his memoir, “Friends, Lovers and the Big Terrible Thing,” Perry revealed that he was “seconds away” from proposing to Caplan, who was his girlfriend of six years.
They met at her 23rd birthday party when he was 36 but both had “intimacy issues,” Hello reported.
“For Christmas, I’d paid a huge amount of money for an artist to paint the two of us,” he said in the book, according to Hello.
“My plan was to give her the painting and then ask the question…well, I never asked it. I gave her the present and she was really moved by it, saying, ‘Matty, my little heart – what you’re doing to my little heart,” he wrote.
“And it was time, all I had to do was say, ‘Honey, I love you. Will you…’ But I didn’t say it. All my fears reared up like a snake. I immediately went into Chandler [expletive] Bing mode. ‘Hey, hey, hey!’ I said to her consternation, ‘look at this!'”
According to Hello, Perry lamented that he might have had a wife and kids if he had chosen differently, but Caplan went on to marry someone else.
Matthew Perry Once Dated Actress Julia Roberts
Heavy/GettyMatthew Perry died on Julia Roberts’ birthday.
According to People Magazine, Perry dated Roberts after she guest starred on “Friends.”
He even met her family. “I did let her in, both figuratively and literally, and a relationship began,” the actor wrote, according to People. “We would already be a couple by the time we started filming the Friends Super Bowl episode.”
Perry ended the relationship after only a few months, according to People.
“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.”
Matthew Perry Made Out With Valerie Bertinelli
GettyValerie Bertinelli onstage during Project Angel Food’s Lead with Love 4 – A Fundraising Special on KTLA at KTLA 5 on June 24, 2023 in Los Angeles, California. (Photo by Tommaso Boddi/Getty Images for Project Angel Food)
According to his memoir, Perry said he “secretly made out” with Bertinelli, but they never dated, Life and Style reported.
According to Entertainment Weekly, Perry wrote in his book, “I fell madly in love with Valerie Bertinelli, who was clearly in a troubled marriage. My crush was crushing; not only was she way out of my league, but she was also married to one of the most famous rock stars on the planet, Eddie Van Halen.”
He continued, “As the night progressed, it was clear that Eddie had enjoyed the fruits of the vine a little too hard, one more time, and eventually he just passed out, not ten feet away from us, but still. This was my chance! If you think I didn’t actually have a chance in hell you’d be wrong, dear reader — Valerie and I had a long, elaborate makeout session.” The next day she acted like nothing happened, EW reported.
Matthew Perry Had a ‘Make-Out Session’ With Gwyneth Paltrow
GettyGwyneth Paltrow in 2023.
According to Life and Style, Perry revealed in his memoir that he once had a “make out session in a closet” with Paltrow back in 1994.
Tricia Fisher & Matthew Perry Dated When He Was 18
GettyTricia Fisher
Perry dated Tricia Fisher, Carrie Fisher’s half-sister, when he was 18, People reported.
“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 in his book.
They eventually broke up but dated years later. “Years later, Tricia and I would date again, while Friends was at its peak,” Perry wrote in his book, according to People. “She didn’t abandon me, but old fears crept up, and I ended the relationship.”
Gabrielle Allan Is a Producer Who Dated Matthew Perry
GettyGabrielle Allan
According to Biography.com, Perry also dated producer Gabrielle Allan.
People Magazine reported that Perry described in his memoir how alcohol addiction affected his life at that time.
“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 wrote, adding that she would “go on to write for Veep and a bunch of other stuff and be a friend for life.”
Jamie Tarses Was a Producer Who Dated Matthew Perry
GettyJamie Tarses
According to Buzzfeed, Tarses was an NBC producer who may have played a role in getting Perry the role on “Friends.”
They later went on to date, People reported, adding that he broke it off after she helped him recover from substance abuse.
“I need time to process being sober,” Perry wrote, according to People. “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.”
Rachel Dunn Was a Fashion Student Described as Matthew Perry’s Ex Girlfriend
GettyMatthew Perry with Rachel Dunn
She was a fashion student described by Perry as “the ex-girlfriend of his dream,” in his memoir, according to the U.S. Sun.
Natasha Wagner
GettyNatasha Wagner
The U.S. Sun reported that Perry dated the daughter of Robert Wagner and Natalie Wood, describing her as “beautiful, smart, caring and sexy.”
Cameron Diaz
GettyCameron Diaz
According to Life and Style, Perry’s book also revealed that he had an encounter with Diaz after she and Justin Timberlake broke up in 2007.
He wrote that he was “set up” with Diaz, Life and Style reported.
READ NEXT: Matthew Perry’s Cause of Death.