Matthew Perry’s death shocked the world of entertainment. The beloved Friends actor, who starred as the sarcastic and funny Chandler Bing on the show, was only 54 when he died. He had been struggling with alcohol and drug addiction for many years; however, not long ago, he finally became sober. Now, condolences to Perry are coming in from everywhere, including his Friends co-stars, and previous romantic connections.

One mourning Perry’s death is Molly Hurwitz, his former fiancée. The couple was engaged for a while but eventually split in 2021. While their love story was short, the two formed a strong bond, staying in touch.

Matthew Perry formed many strong bonds in his life. One that stuck with him for a very long was with actress Ione Sky, with whom he made his film debut in 1988. They stayed great friends until the end. And now, she’s decided to share his last-ever message sent to her, just some days before his passing.

Matthew Perry died on October 28, aged 54, in an apparent drowning accident at his Los Angeles home.

Matthew Perry dead at 54

The Los Angeles police are still investigating the details surrounding Perry’s death. CNN sources say there is currently no foul play suspected. However, it remains under investigation by the Los Angeles Police Department Robbery-Homicide Division. On Wednesday, initial findings suggested that the Friends stars’ death appears to have not been attributed to a fentanyl or meth overdose.

In the last few days, former colleagues, friends, and others have paid tribute to the late actor, famously portraying Chandler Bing on Friends. 

In a statement to People Monday, his co-stars on the sitcom, Jennifer Aniston, Courteney Cox, Lisa Kudrow, Matt LeBlanc, and David Schwimmer, paid tribute to their late co-star and friend.

“We are all so utterly devastated by the loss of Matthew. We were more than just cast mates, we are a family,” the statement read. “There is so much to say, but right now we’re going to take a moment to grieve and process this unfathomable loss.”

“In time we will say more, as and when we are able,” they continued. “For now, our thoughts and our love are with Matty’s family, his friends, and everyone who loved him around the world.”

Matthew Perry
Steven Ferdman/Patrick McMullan via Getty Images

Matthew Perry lived a very complicated life, struggling with addiction for many years. But on the other hand, there were, of course, also some happy moments, including being in love. Still, the late actor never married or had children.

Over the years, Perry was in several high-profile relationships, including dating Julia Roberts and Lizzy Caplan.

Matthew Perry’s dating history – short fling with Julia Roberts

Matthew Perry and Julia Roberts had a short fling, and it was the Friends superstar who broke up with her. However, before they began dating, there were plenty of sparks.

In his 2022 memoir, Friends, Lovers, and the Big Terrible Thing, Matthew Perry recalled how they faxed each other back and forth for three months.

“I was so excited that some nights I would find myself out at some party sharing a flirtatious exchange with an attractive woman and cut the conversation short so I could race home and see if a new fax had arrived,” he wrote. “Nine times out of 10, one had.”

In 1996, for the Superbowl special episode of Friends, they wanted to get Julia Roberts on as a guest star. But it was all thanks to Matthew Perry that it happened.

Behind the scenes, Perry charmed Roberts into starring in the episode. But she had one demand: Being in Matthew’s character, Chandler Bing’s, storyline. However, there was one more thing she wanted from Matthew Perry.

“Matthew asked her to be on the show. She wrote back to him, ‘Write me a paper on quantum physics, and I’ll do it,’” Friends co-creator Kevin Bright told The Hollywood Reporter.

It might appear impossible for someone unfamiliar with that field to do it. But Matthew Perry was a dedicated person.

Matthew Perry, Julia Roberts

“But first, I had to woo her,” he wrote in his memoir. “Her reply was that if I adequately explained quantum physics to her, she’d agree to be on the show. 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.”

Matthew Perry and Julia Roberts flirted over fax

“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. Not only did Julia agree to do the show, but she also sent me a gift: bagels — lots and lots of bagels. Sure, why not? It was Julia f—ing Roberts,” he continued.

The Pretty Woman star was set to appear on the Superbowl special episode of Friends. Throughout the series’ lifetime, many guest stars, including Danny DeVito, Brad Pitt, and, of course, Tom Selleck (though he had a more prominent recurring role), appeared. But for Matthew Perry, having Julia Roberts on the show was undoubtedly the most special one. And the chemistry between them onscreen was apparent.

“They may have met before the episode, but she was interested in him from afar because he’s so charming. There was a lot of flirting over faxing. She was giving him these questionnaires like, ‘Why should I go out with you?’” Friends staff writer Alexa Junge explained. “And everyone in the writers’ room helped him explain to her why.”

Sadly for Matthew Perry’s character Chandler Bing, Julia Roberts’ character, his former classmate Susie, wasn’t there to be charmed. Instead, she flirted with him to get revenge for a prank he pulled on her in fourth grade. Meanwhile, when she was not on camera but standing behind the stage watching Perry act, it was obvious that something was happening between them. If not, it was bound to happen.

“I remember standing with her on the sidelines. She kept saying, ‘Chandler’s so funny!’ And I’m like, ‘I wrote every one of those lines!’” Friends writer Jeff Astrof recalled.

Matthew Perry, Julia Roberts
Liaison

He added, “I don’t know if she fell in love with Matthew on the spot, but they soon started dating. I felt like Cyrano (de Bergerac). Like, Chandler is going to date Julia Roberts, and I’m going to go home to my horrible girlfriend. That’s my memory of that episode.”

Why Matthew Perry broke up with Julia Roberts

After the episode had aired, Perry and Roberts began dating. Sadly, their romance lasted only two months as Matthew Perry broke up with her.

In his memoir, the late actor revealed that he felt “constantly worried” that Julia Roberts would be the one calling it quits. Therefore, he decided to do it himself.

“Dating Julia Roberts had been too much for me,” Perry wrote in his memoir. “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.”

Matthew Perry was involved in several relationships. He never married nor had children. But in 2020, he announced his engagement to literacy manager Molly Hurwitz.

At the time they met, Perry was in and out of rehab for his addiction illness. He once said he spent approximately 7 million dollars over the years to get clean, being to rehab 15 times.

But that one time while in rehab, in 2020, when he and Molly had dated for about two years, he decided to propose to her.

Writing in Friends, Lovers and the Big Terrible Thing, Matthew Perry explained how he was in an expensive Swiss rehab facility when proposing to her.

Matthew Perry’s engagement to Molly Hurwitz

He tragically recalled being lonely and under the influence of drugs at the time.

“I bought her a ring because I was desperate that she would leave me,” he wrote, without actually using Hurwitz’s name, I didn’t want to be this injured and alone during Covid. 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 added.

Shortly after their engagement was made public, Perry gave a comment to People Magazine. And man, was he happy,

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

When he got out of rehab and returned home to Los Angeles, Perry was nearly sober. However, he was shocked when he realized that he had proposed and, at the same time, lived with Molly and her dogs. He didn’t remember ever proposing to her.

“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?” Perry wrote.

“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?’”

Matthew Perry

The Friends actor continued, “I didn’t remember — needless to say, we broke up,” he curtly noted.

“He would love that the world is talking about how talented he was”

In June 2021, Matthew Perry and Molly Hurwitz decided to call off their engagement.

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

Shortly after Matthew Perry’s tragic passing, Molly Hurwitz took to Instagram to honor her former fiancé. She said she will remember him as someone who had a “profound impact” on her life.

“He would love that the world is talking about how talented he was,” she began her post. “And he really was very talented.”

“But, I obviously knew that man in a very different way, too,” she continued, touching on their difficulties during their time together. “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.”

“Matty, I feel relief that you are at peace,” Molly Hurwitz ended her post on Instagram.

Matthew Perry

Matthew Perry had many friends and former colleagues who wanted to send their condolences and last messages to him.

Matthew Perry – his longtime friend shares his last message

He debuted in the 1988 film A Night in the Life of Jimmy Reardon, where he starred alongside Ione Skye, who became a great friend.

On Instagram, Ione Skye shared a screenshot of their last-ever conversation and paid tribute to the Friends star.

“Hi! I hope all is well. I was meditating (I meditate now) and ‘In Your Eyes’ started playing. And I instantly thought of how beautiful you are,” Perry wrote in a text message sent to Skye on October 15, in which he referenced the song from her 1989 film Say Anything, according to People.

She replied, “Awe. I love that. Xo,” to which Perry answered, “Hope you are healthy and happy.”

Further, Ione Skye told Matthew it was “good to hear” from him, saying, “I only have nice memories with you.”

Perry said, “Me too. That one afternoon, I was just sitting in my apartment, and there you were!”

If you enjoyed this article about Matthew Perry, perhaps you’d be interested in reading about how the Friends star reportedly ‘never fully got over’ Courteney Cox.

Rest in peace, Matthew Perry. Please share this article on Facebook with friends and family to honor his legacy.