Matthew Perry’s greatest loves and biggest breakups: From Julia Roberts to Lizzy Caplan
At the peak of his fame, Matthew Perry dated some of Hollywood’s most famous women. But one relationship has always haunted the actor.
At the peak of his fame, Matthew Perry dated some of Hollywood’s most famous women.
The Friends actor had relationships with the likes of Julia Roberts, Cameron Diaz, Gwyneth Paltrow and Yasmine Bleeth, who was the on-screen crush of his character Chandler Bing.
Perry was also linked to stars such as Neve Campbell, Heather Graham and Lauren Graham.
But the star never married or had children, saying it was his failure to propose to actress Lizzy Caplan which always ‘haunted’ him.
In an interview with GQ magazine in October 2022, the actor cited his insecurities for one of the reasons why he never truly settled down.
“I break up with them because I’m deathly afraid that they will find out that I’m not enough, that I don’t matter, and that I’m too needy, and they’ll break up with me,” he said.
Tragically, on October 28, the star died alone in his LA home from an apparent drowning.
Here is a look at Perry’s past relationships – the lessons he learnt and what he had said about it over the years.
Valerie Bertinelli
In his memoir, Friends, Lovers and the Big Terrible Thing, released in November 2022, Perry revealed he had a secret “make-out session” with married actress Valerie Bertinelli, who was his co-star on the sitcom Sydney back in 1990.
“I fell madly in love with Valerie Bertinelli, who was clearly in a troubled marriage,” Perry wrote.
“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.”
Perry said he and Bertinelli finally caved in to their chemistry and shared a “make-out session” one time, while Valen Halen was passed out drunk a few feet away.
“Valerie and I had a long, elaborate make-out session,” he wrote of his co-star, who was married to Van Halen from 1981 to 2007.
“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 said his feeling ran deep feelings for Bertinelli, it was clear she regretted the kiss as the next day she “made no mention” of what transpired and behaved “as she should have”.
“I quickly got the hint and also played the role I was supposed to, but inside I was devastated,” he wrote, adding that there were many “tearful” nights that followed and their show got cancelled after one season.
But that was a good thing as he “didn’t have to see Valerie anymore”.
Gabrielle Allan
Perry’s relationship with aspiring producer Gabrielle Allan – or Gaby, as he affectionately called her – was rather significant as it was during their time together that he realised he had a problem with alcohol.
“Love of alcohol had indeed become the helmsman of my life, but I don’t think I realised 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 become a producer on the TV series Veep and was “a friend for life”.
He recalled one instance when he “first felt the obsession for alcohol” after they went to a magic show in University City and returned to Allan’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,” he wrote.
Gwyneth Paltrow
In his memoir, Perry also opened up about his relationship with Gwyneth Paltrow.
He particularly remembered their “make-out session in a closet” at a party back in 1994 before they both became famous.
“At some big party we slipped off into a broom cupboard and made out,” he wrote. “We were both still unknown enough that it didn’t make it to the tabloids.”
While promoting his memoir, Perry wondered if the actress would oppose being mentioned in his book, telling GQ, “Hopefully, she’ll find it to be a cute story. It’d be bad if Gwyneth Paltrow hated me; I wouldn’t like that.”
Paltrow only has love for Perry after all these years, as she describes in a heartfelt tribute to the star upon hearing of his death.
“I met Matthew Perry in 1993 at the Williamstown Theater Festival in Massachusetts. We were both there for most of the summer doing plays,” she shared on Instagram alongside a photo of Perry.
“He was so funny and so sweet and so much fun to be with. We drove out to swim in creeks, had beers in the local college bar, kissed in a field of long grass. It was a magical summer.
“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.”
Paltrow said they remained friends after their brief relationship, but lost touch over the years.
“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.”
Julia Roberts
Julia Roberts was already a superstar before she made a cameo on Friends in 1996, playing his character Chandler’s former classmate Susie, who was seeking revenge after a childhood prank left her humiliated.
According to Perry, Roberts said she would only do the guest role if she could have a storyline along his wisecracking character. As a thank you, Perry sent her a bouquet of red roses.
“I sent her three dozen red roses and the card read, ‘The only thing more exciting than the prospect of you doing the show is that I finally have an excuse to send you flowers,’” he recalled in his memoir.
The pair then embarked on a three-month relationship but Perry ultimately ended it as he felt inadequate to be dating a major movie star – he felt like she was “slumming it with a TV guy”.
“Dating Julia Roberts had been too much for me. I had been constantly certain that she was going to break up with me,” he wrote. “Why would she not? I was not enough; I could never be enough; I was broken, bent, unlovable.”
“So instead of facing the inevitable agony of losing her, I broke up with the beautiful and brilliant Julia Roberts,” he confessed.
Rachel Dunn
The actor dated former fashion student Rachel Dunn for two years before splitting in 2005, around the time Friends wrapped.
In his memoir, he called her “the ex-girlfriend of his dreams”.
According to People, there was no big fallout or incident that triggered their split – Perry just wanted to focus on his sobriety.
“There was no drama involved [in the break-up], just a commitment by Matthew to stay focused on his sobriety,” a source told the outlet.
Cameron Diaz
Perry was set up on a date with Cameron Diaz shortly after her split with Justin Timberlake in 2007 following a four-year relationship.
He recalls in his memoir that the pair met at a group dinner party where Diaz was “immediately stoned” and “wasn’t interested in [him] at all”.
After he said “something witty” to the Charlie’s Angels star during a game of Pictionary, he claims she “accidentally” hit his face while aiming for his shoulder.
“Are you f***ing kidding me?” he remembered replying.
Lizzy Caplan
The actor’s longest relationship was with Mean Girls star Lizzy Caplan, although they kept most of their romance under wraps for most of their time together.
Perry never mentioned Caplan by name in his memoir, but he revealed they were initially “friends with benefits”.
They would end up dating for six years and almost got engaged before parting in 2012, and he said the break-up had haunted him ever since.
“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.”
Molly Hurwitz
Perry’s next and last publicly known relationship was with literary manager Molly Hurwitz.
The pair started dating in 2018 and by 2020, he popped the big question.
“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.”
Perry proposed while he was in rehab in Switzerland where he said he was “high on 1800 milligrams of hydrocodone” at the time.
“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,” he recalled in his memoir.
“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.”
“Back in LA one more time, trying to sober up, I think, Wait … how did I get engaged? There are dogs living in my house. How did this happen?” he continued.
“I had asked her parents, begged for her hand while high, and put up with the dogs. That’s how scared I was of being abandoned.”
However, the relationship did not last and they called it quits in 2021.
“Sometimes things just don’t work out and this is one of them,” he said in a statement to People after their split. “I wish Molly the best.”
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