Matthew Perry dating history: Inside his relationships with Lauren Graham and more

Tributes have been pouring in for Matthew Perry following the actor’s death, including one touching message from Gwyneth Paltrow on Instagram.

Paltrow, 51, called the actor “so funny and so sweet” and said she and Perry had had a summer fling in the ‘90s, just before he rose to fame with “Friends.”

Perry, who died at 54 on Oct. 28 after an apparent drowning, was candid about his romantic past in his 2022 memoir, “Friends, Lovers, and the Big Terrible Thing.”

While he did not mention some of his past girlfriends by name in the book, he opened about his relationships with several of his past partners, including Paltrow and Julia Roberts.

Perry was never married, although he was at one time engaged.

Here’s a look at some of Perry’s most highest-profile relationships through the years.

Perry was close to Lauren Graham, though she has said they 'never exactly dated'

Rumors have long circulated online that Perry and Graham, 56, dated briefly in the early 2000s, but the actors have never said they were an item.

They did cross paths multiple times over the years, co-starring in the 2008 movie “Birds of America."

Graham also appeared alongside Perry in one episode of his reboot of “The Odd Couple,” which ran from 2015 to 2017.

Ellen DeGeneres teased Graham about the romance rumors with Perry multiple times through the years on her talk show.

“You always make fun of me for not going out with him, and I keep telling you he’s just my friend,” Graham once told DeGeneres.

Graham mentioned Perry in her 2016 memoir, “Talking As Fast As I Can.”

“The only bright spot, dude-wise, was at an event where I met Matthew Perry,” she wrote. “He became my longtime Friend Who I Almost But Never Exactly Dated, or FWIABNED.”

The “Gilmore Girls” star later congratulated Perry on the release of his memoir.

“Happy, happy pub day, @MatthewPerry! xL,” she wrote in a post on the X platform, adding two green hearts and a shamrock emoji.

Perry included a photo of him and Graham in his memoir, showing the “Parenthood” actor resting her head on his shoulder.

“Me and the beautiful Lauren Graham,” he captioned the picture.

He was once engaged to literary manager Molly Hurwitz

Perry never tied the knot, but he was at one time engaged to literary manager Molly Hurwitz.

People reported in November 2020 he'd popped the question to Hurwitz, whom he had been dating since 2018.

“I decided to get engaged,” Perry told People. “Luckily, I happened to be dating the greatest woman on the face of the planet at this time.”

Shortly after their engagement went public, Perry shared a now-deleted Instagram photo of Hurwitz wearing a top printed with a classic Chandler Bing turn of phrase: “Could this BE any more of a T-shirt?”

The couple split in 2021. Perry confirmed their breakup in a statement to People.

“Sometimes things just don’t work out and this is one of them,” he said. “I wish Molly the best.”

Perry did not mention Hurwitz by name in his memoir. He did discuss being engaged to a woman during the COVID-19 pandemic.

“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,” he continued.

Later in the book, Perry described how his relationship with his fiancée deteriorated after his stay at a rehab facility in Switzerland.

“I was sobering up,” he wrote. “That meant that I was slowly beginning to realize that I was engaged, lived with a woman and two dogs. Needless to say, I was not ready for any of this. You live with me? We live together? We have kids’ names picked out, the whole nine yards, which is the name of a movie I once made?

“You went down on one knee to propose, which really hurt your stomach, remember?” he continued. “I didn’t remember — needless to say, we broke up.”

Perry and Julia Roberts dated during the early days of 'Friends'

Perry connected with Roberts before she guest-starred in an episode from Season Two of “Friends” called “The One After the Superbowl.”

As Perry wrote in his memoir, Roberts had been approached to appear in the episode, but said she would only do the show if she could be part of Chandler Bing’s storyline.

Perry said he soon set out to “woo” the Oscar winner.

He sent Roberts three dozen red roses and a card that 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.”

Not yet convinced, Roberts apparently sent back a flirtatious challenge.

“Her reply was that if I adequately explained quantum physics to her, she’d agree to be on the show,” Perry wrote. “Wow. First of all, I’m in an exchange with the woman for whom lipstick was invented, and now I have to hit the books.

“The following day, I sent her a paper all about wave-particle duality and the uncertainty principle and entanglement, and only some of it was metaphorical,” he added.

That response worked, and before long they were conducting a courtship — by fax.

“Somewhere in the world, there is a stack of faxes about two feet long — a two-foot-long courtship, filled with poems and flights of fancy and two huge stars falling for each other and connecting in a beautiful, romantic way,” Perry wrote.

In his book, Perry wrote that he was “walking on air” while dating Roberts.

However, he said his anxiety over being abandoned — a recurring theme throughout his memoir — ultimately contributed to his split with the “Notting Hill” star.

“Dating Julia Roberts had been too much for me,” he wrote. “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, unlovable.

“So instead of facing the inevitable agony of losing her, I broke up with the beautiful and brilliant Julia Roberts,” he continued. “She might have considered herself slumming it with a TV guy, and TV guy was now breaking up with her. I can’t begin to describe the look of confusion on her face.”

Gwyneth Paltrow says she and Perry spent a 'magical summer' together

Following Perry’s death, Gwyneth Paltrow shared a tribute to the actor on Instagram, writing that she and Perry had had a summer fling just before “Friends” catapulted him to fame.

“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,” she captioned a headshot of Perry from his earlier acting days.

“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,” Paltrow’s caption continued. “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."

Perry also described his time with Paltrow in his memoir, saying they met at a party and “slipped off into a broom cupboard and made out."

At the time, the first episodes of “Friends” had been filmed but had not yet aired. Perry recalled famed TV director James Burrows telling him and his “Friends” co-stars to enjoy anonymity while it lasted.

“This was the last summer of my life when I could make out at a party with a beautiful young woman called Gwyneth,” Perry wrote in his memoir, “and no one, save Gwyneth and I, cared."

In her tribute to Perry following his death, Paltrow said she and the actor "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," she continued. "I hope Matthew is at peace at long last. I really do.”

This article was originally published on TODAY.com