Matthew Perry’s famous exes and how they remember him

The late Friends star holds a special place in many people's hearts.

WEST HOLLYWOOD, CALIFORNIA - NOVEMBER 17: Matthew Perry attends the GQ Men of the Year Party 2022 at The West Hollywood EDITION on November 17, 2022 in West Hollywood, California. (Photo by Phillip Faraone/Getty Images for GQ)
Matthew Perry had some well-known exes. (Getty Images for GQ)

Matthew Perry's best known character, Chandler Bing, was known for his romance with screen wife Monica Geller in Friends – but what about the late star's real life love stories?

Perry, who passed away unexpectedly on Saturday, 28 October, detailed many of his relationships with high-profile stars in his 2022 memoir Friends, Lovers and The Big Terrible Thing.

Although the star, who died aged 54, did not marry, he did get engaged during his final serious relationship and had opened up on his regrets about not marrying another ex.

His former flames have begun to share their memories of the late star – with both Gwyneth Paltrow and Molly Hurwitz paying tribute to him.

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Gwyneth Paltrow

A-list star Gwyneth Paltrow reflected on her brief romance with Perry in 1993 following his death.

Looking back, the actor fondly remembered their "magical summer" and kissing in the long grass ahead of Perry's big break in Friends.

She wrote on Instagram: "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. 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.

"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 (1995 - 1996)

304422 21: Actor Matthew Perry and actress Julia Roberts hug each other on the set of
Matthew Perry and Julia Roberts hug each other on the set of Friends. (Liaison)

Perry's first romance with a big Hollywood star was with Julia Roberts, who he dated for around a year.

Their relationship began after Friends bosses approached Pretty Woman star Roberts to take a guest role in the show and 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 admitted 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?"

He added: "So instead of facing the inevitable agony of losing her, I broke up with the beautiful and brilliant Julia Roberts."

Yasmine Bleeth (1996)

Yasmine Bleeth starred in Baywatch. (PA/Alamy)

In the early days of his Friends superstardom, Perry dated another star of one of TV's biggest hits - Baywatch's Yasmine Bleeth.

Perry's Friends alter-ego Chandler often mentioned his crush on Bleeth during episodes of the sitcom, both before and after their fling.

Maeve Quinlan (2002 - 2003)

Maeve Quinlan and Matthew Perry during Stars Make Their Voices Heard at a Silent Auction for Lollipop Theater Network at Private Home in Beverly Hills, California, United States. (Photo by Donato Sardella/WireImage for Lollipop Theater Network)
Maeve Quinlan and Matthew Perry. (WireImage for Lollipop Theater Network)

In the late 90s, Perry was rumoured to be dating Neve Campbell after they starred together in Three to Tango, although neither ever spoke about the alleged romance.

However, he did have a short relationship with The Bold and The Beautiful actor Maeve Quinlan from 2002 to 2003.

Lauren Graham (2003)

Lauren Graham and Matthew Perry during 8th Annual Lili Claire Foundation Benefit - Show & Backstage at The Beverly Hilton in Beverly Hills, CA, United States. (Photo by Jesse Grant/WireImage for Fusion PR _LA)
Lauren Graham and Matthew Perry. (WireImage for Fusion PR _LA)

The actor's dating life was especially busy in 2003, with a rumoured romance with Heather Graham that appeared to only last for a few weeks before getting together with Lauren Graham for a few months.

In typical Perry fashion, he kept the details of their relationship private, but it seemed to end on good terms as they continued to work together after their split.

Graham and Perry appeared together in TV series Studio 60 on the Sunset Strip, and were also co-stars in the 2015 sitcom version of The Odd Couple.

Rachel Dunn (2003 - 2005)

Matthew Perry & Rachel Dunn during 2003 Emmy Creative Arts Awards - Arrivals at Shrine Auditorium in Los Angeles, California, United States. (Photo by Gregg DeGuire/WireImage)
Matthew Perry with Rachel Dunn. (WireImage)

One of Perry's most high-profile romances was with Rachel Dunn, but it also came with some controversy because of their large age difference.

Dunn, just 19 when she met a 35-year-old Perry, was a fashion student from Cambridge who had relocated to the US and spent two years with the actor.

Perry credited his girlfriend with bringing stability to his life and dated her during a sober period, but they eventually split with sources claiming that there was no drama and that Perry wanted to focus on his sobriety.

Lizzy Caplan (2006 - 2012)

Lizzy Caplan at the Chanel Artists Dinner at Balthazar Restaurant on June 12, 2023 in New York, New York. (Photo by Lexie Moreland/WWD via Getty Images)
Matthew Perry quietly dated Lizzy Caplan for six years. (WWD via Getty Images)

By far Perry's longest relationship was with Mean Girls star Lizzy Caplan, who he dated for six years.

However, the couple managed to keep things so secret that no one even knew of their split until a year and a half after it happened.

Most of the details of their relationship emerged in Perry's book, where he opened up on his regret and heartbreak at not asking Caplan to marry him.

Perry told how he had commissioned an artwork for her and had been planning on popping the question, but couldn't bring himself to ask her.

He wrote in 2022: "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 (2018 - 2021)

The closest Perry came to marriage was in his final serious relationship, with literary agent Molly Hurwitz who was more than 20 years younger than him.

Perry confirmed that he had got engaged to Hurwitz, but by 2021 the engagement had been quietly called off, although it wasn't clear when the relationship ended.

Making 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 his death, Hurwitz detailed her deep love for the late star and revealed the impact their relationship had on her life.

She wrote in an Instagram post: "While I loved him deeper than I could comprehend, he was complicated, and he caused pain like I’d never known.

"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."

Hurwitz opened up about her sweet memories of the late star and praised his acting talent.

She wrote in an Instagram post: "He would love that the world is talking about how talented he was. And he really was very talented. As the Friends reunion was approaching, we rewatched the show together. "F***, I was so good!!!…See what I did there???" 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."

In her post, she also referenced Perry's struggles with substance abuse.

"I’d be remiss if I didn’t mention Al Anon, an invaluable resource for those who love someone struggling with this destructive disease," she wrote. "Matty, I feel relief that you are at peace."