Matthew Perry’s famous ex-girlfriends, from Julia Roberts to Lizzy Caplan

Matthew Perry’s most famous character, Chandler Bing, was known for his romance with his on-screen wife Monica Geller in “Friends” – but what about the late star’s real-life love stories?

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

Although the star, who died at the age of 54, did not marry, he got engaged during his last serious relationship and spoke openly about his regrets for not marrying another ex.

His former flames have started sharing 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 the kisses in the tall grass before Perry’s big break in “Friends.”

She wrote on Instagram: “I met Matthew Perry in 1993 at the Williamstown Theater Festival in Massachusetts. We both spent most of the summer there doing theater.”

“He was so funny and so sweet and so much fun to be around. We went out swimming in streams, drank beer at the local college bar and kissed in a field of tall grass.

“It was a magical summer. He had shot the pilot of Friends, but it hadn’t aired yet. He was nervous and hopeful that his big break was about to happen. And it was.

“We remained friends for a while until we grew apart, but I was always happy to see him. I’m super sad today, like so many of us. I hope Matthew finally finds peace. I really do.”

Julia Roberts (1995 – 1996)

Perry’s first romance with a major Hollywood star was with Julia Roberts, whom he dated for about a year.

Their relationship began after Friends bosses asked Pretty Woman star Roberts to guest star on the show. She accepted on the condition that her storyline would involve Chandler.

But the pressure of dating a big star was too much for Perry. In his memoirs, he confessed: “Dating Julia Roberts was too much for me. I was constantly convinced that she was going to break up with me. Why wouldn’t she?”

He added: “So rather than face the inevitable pain of losing her, I broke up with the beautiful and brilliant Julia Roberts.”

Yasmine Bleeth (1996)

In the early days of his “Friends” superstardom, Perry dated another star from one of TV’s biggest hits: Yasmine Bleeth from “Baywatch.”

Chandler, Perry’s alter ego on “Friends,” often mentioned his crush on Bleeth in episodes of the sitcom, both before and after their affair.

Maeve Quinlan (2002 – 2003)

In the late ’90s, there were rumors that Perry was dating Neve Campbell after the two starred together in Three to Tango, but neither of them ever spoke about the alleged romance.

However, from 2002 to 2003 he had a brief relationship with “The Bold and the Beautiful” actress Maeve Quinlan.

Lauren Graham (2003)

The actor’s love life was particularly active in 2003. He was rumored to have had a romance with Heather Graham, but it apparently only lasted a few weeks before he started dating Lauren Graham for a few months.

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

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

Rachel Dunn (2003 – 2005)

One of Perry’s most famous romances was with Rachel Dunn, but due to the large age difference between the two, this was also controversial.

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

Perry believed his girlfriend brought stability to his life and dated her during a period of sobriety. However, the two eventually split. Sources say there was no drama and Perry wanted to focus on his sobriety.

Lizzy Caplan (2006 – 2012)

Perry’s longest relationship by far was with Mean Girls star Lizzy Caplan, with whom he was together for six years.

However, the couple managed to keep the matter so secret that no one found out about the separation until a year and a half later.

Most of the details of their relationship come to light in Perry’s book, in which he also reveals his regret and heartache over not proposing to Caplan.

Perry said he had commissioned a piece of art for her and wanted to propose to her but couldn’t bring himself to do it.

He wrote in 2022: “I often think that if I had (asked her to marry me) we would have two kids and a house now. Instead I’m some fool sitting alone in his house at fifty-three.”

Molly Hurwitz (2018 – 2021)

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

Perry confirmed his engagement to Hurwitz, but in 2021 the engagement was quietly broken off, although it was not clear when the relationship ended.

Perry said in a statement about the split: “Sometimes things just don’t work out and this is one of those things. I wish Molly the best.”

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

In an Instagram post, she wrote: “Although I loved him more deeply than I could comprehend, he was complicated and caused pain I had never known.

“No one has had a greater influence on me in my adult life than Matthew Langford Perry. For that, I am eternally grateful for everything I learned from our relationship.”

Hurwitz spoke about her fond memories of the late star and praised his acting talent.

She wrote in an Instagram post: “He would love for the world to talk about how talented he was. And he really was very talented. As the Friends reunion approached, we rewatched the show together. ‘Damn, I was so good!!! … See what I did there???’ We would rewind and study scenes. Our respect and appreciation for humor is something that has bonded us. Being there with him as he rediscovered his brilliance was magical.”

In her post, she also referred to Perry’s battle with drug abuse.

“I would be remiss if I didn’t mention Al Anon, an invaluable resource for those who love someone battling this devastating disease,” she wrote. “Matty, I’m relieved you have found peace.”