There are few stars as beloved as Matthew Perry. From his brilliant comedic timing to his all-too-real ‘Friends’ character, Chandler Bing, there was just something about the late actor that had everyone falling in love with him. And it turns out, celebrities were no different! Below, we take an up-close look at every woman Perry was romantically linked with before his untimely death, and what he had to say about them. Scroll on for more.
Tricia Fisher
At just 18 years old, Perry began dating actress and half-sister of Carrie Fisher, Tricia Fisher. The two met around 1988, when A Night in the Life of Jimmy Reardon finished filming —a movie that starred Perry and River Phoenix.
The couple’s relationship was a steamy one, though, with Perry revealing in his memoir Friends, Lovers and The Big Bad Terrible Thing that Fisher was actually the first person he ever slept with.
“My firmness, at least in my conviction to wait, lasted two months… The make-out sessions that didn’t lead anywhere were beginning to cause both of us to hyperventilate,” he wrote.
Following that, the two did break up for quite a few years, but got back together “while Friends was at its peak,” according to Perry.
“She didn’t abandon me, but old fears crept up, and I ended the relationship.”
Tricia Fisher has been married to Bryan Thames since 2007 and has three kids.
Valerie Bertinelli
After meeting on the sitcom Sydney in 1990, Perry claims that he “fell madly in love” with Valerie Bertinelli and felt bad that she was “clearly in a troubled marriage” with Eddie Van Halen.
Perry then detailed in his memoir that one night, he was over at the couple’s house, and things started to get steamy between him and Bertinelli real quick.
“As the night progressed, it was clear that Eddie had enjoyed the fruits of the vine a little too hard one more time, and eventually, he just passed out, not ten feet away from us, but still, this was my chance,” the actor wrote. “If you think I didn’t actually have a chance in h*ll, you’d be wrong, dear reader.”
“Valerie and I had a long, elaborate make-out session. 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.”
Despite these deep feelings, though, Perry and Bertinelli never dated and instead, she remained with Van Halen until 2007.
Gwyneth Paltrow
Way back in 1993, Perry and actress/model Gwyneth Paltrow embarked on a whirlwind summer romance in Los Angeles, California.
“I met Matthew Perry in 1993 at the Williamstown Theater Festival in Massachusetts. We were both there for most of the summer doing plays,” says Paltrow. “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.”
Sadly though, the romance ended as quickly as it began, but according to Paltrow, they “stayed friends for a while until we drifted apart, but I was always happy to see him when I did.”
Jamie Tarses
Right before being cast as Chandler Bing in Friends, Perry dated producer Jamie Tarses in 1994, despite her still being legally married at the time.
According to the actor, Tarses was “the most magical, beautiful, and smart [woman]” but during their relationship he needed “time to process being sober,” so he decided the best thing to do was leave.
“In order to adequately pay sweet Jamie back for two years of giving up huge portions of her own very busy and important life by basically being my nurse, I ended our relationship.” Perry wrote in his memoir.
Following their split, Tarses continued to work as a film producer before dying in 2021 from a stroke. She was 56 and is remembered by her two children.
Julia Roberts
Perry’s most talked about relationship came to be in 1995, when he dated Julia Roberts.
“We would already be a couple by the time we started filming the Friends Super Bowl episode [which Roberts guest starred in],” Perry wrote. “I did let her in, both figuratively and literally, and a relationship began.”
Despite that, though, things didn’t work and Perry and Roberts broke up after just two months.
“Dating Julia Roberts had been too much for me,” Perry 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, unloveable.”
Following their split, Roberts got married twice and has three kids.
Gabrielle Allan
Gabrielle Allan—or “Gaby” as Perry called her—dated the actor for an undisclosed time during the 1990s. According to Perry, though, while in that relationship his alcohol addiction began to skyrocket.
“Love of alcohol had indeed become the helmsman of my life, but I don’t think I realized just how much it controlled me until one night when I was out with my girlfriend at the time, Gaby,” the actor wrote.
“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.”
Following their split, Allan went on to produce the hit comedy Veep and, according to Perry, they were friends “for life.”
Rachel Dunn
From 2003 until 2005, Perry dated a woman named Rachel Dunn. Sadly, there are not a lot of details about the couple’s relationship, but in his memoir, the actor did say that she was “the ex-girlfriend of his dream.”
At the time of their relationship, Dunn was 14 years younger than Perry and she was even left as one of Perry’s trust beneficiaries in his will.
Other than that, Dunn has lived a pretty lowkey life post-Perry.
Natasha Wagner
Daughter of Richard Gregson and Natalie Wood, Natasha Wagner was one of Hollywood’s original “nepo” babies. And at some point throughout Perry’s life, she dated him—although the dates remain unknown.
“[She was] beautiful, smart, caring and sexy,” the actor detailed. “She had it all; she was perfect!”
Perry also revealed that he “dated her properly,” which led them to eventually split up.
Yasmine Bleeth
Also during the 1990’s Perry had a love affair with Baywatch star Yasmine Bleeth.
“I was dating one of the women on my list of five celebrity crushes,” the actor wrote in his memoir. “Yasmine Bleeth was stunningly beautiful, and I couldn’t believe she’d even talk to me.”
Sadly, just like the tide, this couple’s relationship eventually went out.
Cameron Diaz
Cameron Diaz and Perry dated briefly in 2007 after being set up by a friend. Sadly, the relationship was doomed from the get-go, because right as they began dating, Diaz got “immediately stoned” and “wasn’t interested in [him] at all.”
The actress then “accidentally” punched Perry in the face. The two naturally went their separate ways.
Lizzy Caplan
For six years, Perry dated Mean Girls actress Lizzy Caplan and even considered proposing to her, according to the actor his “fears reared up like a snake,” causing the two to split up in 2012.
“I often think if I’d asked [her to marry me], now we’d have two kids and a house,” noted Perry. “Instead, I’m some schmuck who’s alone in his house.”
To this day, Caplan was Perry’s longest-known relationship.
Molly Hurwitz
Perry’s final relationship was with literary manager Molly Hurwitz. The two met in 2018, got engaged in 2020, but sadly called it quits the following year.
“Sometimes things just don’t work out and this is one of them,” Perry said of their split. “I wish Molly the best.”
Hurwitz did comment on Perry’s death in 2023, saying, “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 doesn’t have any public social media and mainly remains out of the spotlight.
