Matthew Perry's Dating History: From Julia Roberts To Lizzy Caplan

Matthew Perry, who died October 28, 2023 at age 54, didn't have the easiest time when it came to love. While the "Friends" star enjoyed a string of relationships in the public eye, including several famous women, he was notoriously private when it came to speaking publicly about his love life; he did, however, confirm that some of the reports about celebrities he'd been linked to weren't exactly true. Speaking to People in September 2002, Perry coyly shared he was "single and enjoying [himself]" after hitting the headlines for a number of rumored romances. "I've dated a few people over the summer. Some mentioned in magazines I've never met. Some I was just having coffee with," he claimed.

Although Perry was known to have gotten cozy with a few of his co-stars (more on that later), one place things never got romantic was on the set of "Friends." Speaking to Access in May 2021, Perry confirmed while reuniting with his co-stars that they had a rule that meant none of the cast could get together — despite David Schwimmer and Jennifer Aniston totally crushing on one another in the early days. "If we were hooking up or any strangeness going on that might mess with things," he explained.

So, given that Schwimmer, Aniston, Lisa Kudrow, Courteney Cox, and Matt LeBlanc didn't pop up in Perry's dating history, read on for a look at a timeline of Matthew Perry's dating history.

After having his first drink at age 14, Matthew Perry's lifelong relationship with alcohol was in its infancy when the teenager's early sexual experimentation led him to conclude he was impotent — not realizing it was all that drinking that led to his inability to perform. It wasn't until he was 18, and began dating Tricia Fisher (half-sister of Carrie Fisher) that he made the connection. 

As he wrote in his 2022 memoir, "Friends, Lovers, and the Big Terrible Thing," he initially told Fisher he was planning to remain a virgin until his wedding night — a cover for his presumed impotence. "My firmness, at least in my conviction to wait, lasted two months," Perry wrote (via PopSugar). Perry's plan lasted until Fisher got him alone one night and took things to the next level. Perry felt obliged to share his shameful secret with her, but she was undeterred, promising him that everything would work just fine. She was right. "Sure enough, sheer glory for two whole minutes," he wrote (via Yahoo! Entertainment). After Fisher helped him realize there really was no problem, he joked that he paid her back by "sleeping with almost every woman in Southern California."

They broke up, but reconnected and resumed their romance several years later, while Perry was starring on "Friends." Their second stab at love, however, ended much like the first. "She didn't abandon me," he wrote, "but old fears crept up, and I ended the relationship."

In his memoir, Perry also wrote about dating Gabrielle Allan, a writer and producer whose credits include "Scrubs," "Veep" and Sarah Jessica Parker's HBO series "Divorce." While Perry didn't elaborate on how long they were together, he recalled that he was 21, which would place their romance around 1990.

In Perry's account, via an excerpt in PopSugar, it was during his time with Allan — whom he called Gaby — that he came to realize just how problematic his drinking had become. "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," he wrote.

According to Perry, they'd returned to her home after taking in a magic show, and he was hankering for a drink — badly. "Gaby didn't have any alcohol at home, which is, of course, totally fine, but for me at the age of 21, all of a sudden this creeping feeling came over me for the first time," he recalled. "I felt my blood on fire for more to drink."

In 1990, Matthew Perry landed a role in the short-lived sitcom "Sydney," in which he played the brother of star Valerie Bertinelli's titular private investigator. As he revealed in his memoir, excerpted by Rolling Stone, Perry was head over heels for his co-star, but realized she was "way out of my league" — not to mention that she was also "married to one of the most famous rock stars on the planet, Eddie Van Halen."

Perry was nevertheless smitten, and he fantasized that she'd leave the guitarist for him and they'd spend the rest of their lives together. His hopes were raised significantly when he was hanging out with the couple at their home one night, and Van Halen wound up over-imbibing to the point that he passed out. "This was my chance!" Perry wrote. "If you think I didn't actually have a chance in hell, you'd be wrong, dear reader — Valerie and I had a long, elaborate makeout session ... I told her I had thought about doing that for a long time, and she had said it right back to me." As it turned out, Perry was crushed when he saw her the next day, and she didn't acknowledge what had happened. 

Bertinelli seemingly confirmed Perry's account in a TikTok video. "Anyone misbehave in their 20s and early 30s?" she wrote. "Are you mortified?"

Among the many revelations in Matthew Perry's memoir was his brief fling with Gwyneth Paltrow in the summer of 1994. As he wrote, he was on the cusp of stardom, awaiting the debut of "Friends" that fall, when he met Paltrow in Williamstown, Massachusetts. "She was doing a play there, and I was visiting my grandfather," he wrote, as excerpted by Insider. "At some big party, we slipped off into a broom cupboard and made out. We were both still unknown enough that it didn't make it to the tabloids ... This was the last summer of my life when I could make out at a party with a beautiful young woman called Gwyneth and no one, save Gwyneth and I, cared."

After the book's publication, Perry told GQ that "hopefully, she'll find it to be a cute story ... it'd be bad if Gwyneth Paltrow hated me; I wouldn't like that."

He needn't have worried. After Perry's passing, Paltrow took to Instagram to share a sweet tribute to the late actor, referencing their brief romance. "He was so funny and so sweet and so much fun to be with," she wrote. "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."

In 1995, Matthew Perry had a high-profile romance with Julia Roberts after she guest-starred on "Friends."

They actually knew each other prior, as it was Perry who orchestrated Roberts' guest appearance. "Friends" executive producer Kevin Bright told The Hollywood Reporter that Perry asked her to take part and she responded by telling him she would if he wrote her a paper on quantum physics. Perry did and faxed it over the very next day. Staff writer Alexa Junge revealed that those working on the show helped things go from platonic to more, admitting Roberts "was interested in him from afar" and that the two would flirt on set. "She was giving him these questionnaires like, 'Why should I go out with you?' And everyone in the writer's room helped him explain to her why," Junge added.

The romance didn't last long, due to Perry's anxiety that she'd break up with him. "Dating Julia Roberts had been too much for me," Perry wrote in his memoir, via an excerpt in ET Canada. "I had been constantly certain that she was going to break up with me. Why would she not?" So, to prevent himself from being dumped, Perry broke up with her first. "Instead of facing the inevitable agony of losing her, I broke up with the beautiful and brilliant Julia Roberts," he wrote. "I can't begin to describe the look of confusion on her face."

Chandler Bing would have been pretty jealous of this one. Matthew Perry actually lived his infamous "Friends" character's dream by dating actor and '90s star Yasmine Bleeth, who's probably best known for playing Caroline Holden on "Baywatch," as well as for her roles in "Ryan's Hope" and "One Life to Live."

According to the International Business Times, the two were an item for a few months in 1996 and, although neither seems to have spoken very publicly about their time together, Bleeth's name was brought up on the show a few times in the earlier seasons. As superfans will remember, in Season 3, Episode 21, "The One With the Chick and the Duck," Chandler can be seen speaking to his newly adopted chick about Bleeth while watching her in an episode of "Baywatch." 

"That's Yasmine Bleeth. She's a completely different kind of chick. I love you both. In very different ways," he said. "Love"? Despite being a shorter romance, it sounds like things may have gotten pretty serious to us!

Matthew Perry got close to another of his co-stars when he began dating Neve Campbell. The two famously starred in the 1999 movie "Three to Tango" together, alongside Dylan McDermott, and it's thought the two grew pretty close while filming.

However, this coupling didn't last too long — they'd called it quits before the movie ever even hit movie theatres. This fairly brief romance apparently lasted from February 1999 to June 1999. While it seems neither actually commented on their relationship or breakup publicly, it appears this one probably ended amicably. Despite a fizzled romance, the two seemed to be happy to pose together on the red carpet at the big premiere in October 1999.

The brief romance was probably one of the few good things to come out of the movie, as it didn't exactly do too well with reviewers or at the box office. Despite Perry and Campbell's obvious chemistry while filming, Box Office Mojo puts its earnings at $10.5 million worldwide against a reported budget of $20 million. Ouch. The reviews were pretty scathing too. Roger Ebert claimed it was "mired in a plot of such stupidity" and gave it one star, while Reel Talk Reviews wrote, "Although excellent music adds a bit of joy to 'Three to Tango,' it would take more than a good soundtrack to make this movie swing." Double ouch.

Jamie Tarses, who died in 2021 at age 56, was a powerhouse TV executive who helped develop such hits as "Frasier" and "Friends." It was through her involvement with the latter that she met Matthew Perry, and the two dated for a while. While Perry didn't detail the timeframe of their relationship, he described her as his "sort-of girlfriend" in a passage of his memoir recounting how he fell ill and immediately called Tarses. "Jamie was an angel from God — she drove straight over to my house, poured me into a car, and drove me to the nearest hospital." Perry was ultimately diagnosed with pancreatitis, brought about by alcohol abuse.

That health scare spurred him to get sober. According to Perry, as reported by PopSugar, Tarses was "the most magical, beautiful, and smart" woman, but he felt it was necessary to break up with her in order to maintain his sobriety. "I need time to process being sober," he wrote, somewhat regretfully. "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."

After breaking up with Jamie Tarses, Matthew Perry wrote in his book, "Friends, Lovers, and the Big Terrible Thing," he'd met five different women with whom he felt he could have happily settled down and had children with. "Natasha Wagner was one of those women," he wrote of Wagner, the daughter of actors Robert Wagner and Natalie Wood. "Natasha had it all. She was perfect!" Perry wrote. "But I wasn't looking for perfect. I was looking for more." They dated briefly — albeit in a manner that Perry described as not "properly" — and then went their separate ways. 

Fast forward to 2020. While Perry was driving along the Pacific Coast Highway, he received a call from Wagner, with whom he'd remained friendly over the years. "I'm a mother!" she told him, revealing she and her husband Barry Watson had welcomed a daughter. 

Perry was surprised by his response to her joyous news, which led him to experience an epiphany he found to be heartbreaking. "'She could have had that child with me,' I said, to no one, as I sobbed like a newborn myself," Perry wrote.

Another lengthier romance for Matthew Perry, the star enjoyed a relationship with Maeve Quinlan, who's probably best known for playing Megan Conley in the soap opera "The Bold and the Beautiful" for more than a decade. According to Who's Dated Who, the two went out from 2002 until 2003, and things seemed to be pretty serious between the two.

In typical low-key Perry style, the two didn't appear to gush over their relationship very much — if at all — in public, however, they were photographed together on multiple occasions looking pretty happy and showing off their passion for tennis. The duo was snapped at the 2003 American Airlines Cystic Fibrosis Foundation Grand Slam Celebrity Gala And Tournament in September. A month later, they were getting active again when they were seen in their activewear at the Beverly Hills Celebrity Classic tennis tournament in Los Angeles in October 2002.

It's not clear what went down with these two to make them call it quits, though they appeared to break up on good terms as they met up again in 2006. The former lovers were photographed smiling together at a silent charity auction in Beverly Hills.

In 2003, Matthew Perry was linked to actor Heather Graham. According to Glamour, the "Drugstore Cowboy" actor and "17 Again" star supposedly only dated "briefly" back in the day at the height of "Friends'" popularity, but it seemed like the two may have been friends before things ever turned romantic. 

They were photographed together at least once before the rumors hit the headlines when they both appeared at a casino night in Hollywood in October 2002.

Not much is known about their time together as the two appeared to keep things private, but things seemed to end pretty amicably and they even continued to be photographed together at events. Despite apparently calling it on their relationship the year prior, in February 2004, they appeared together at the 3rd Annual General Motors TEN Fashion Show in Hollywood and were also spotted at the TEN GM Rocks Award Season with Cars event. Could they be any friendlier as exes?

Moving on to one of Matthew Perry's most serious romances — and one of the few he actually spoke about publicly — Perry was with Rachel Dunn when "Friends" came to an end. The two reportedly dated for two years from 2003 to 2005, during which time they stepped out together multiple times and were snapped on various red carpets.

Though Perry previously kept his private life just that, he spoke pretty openly about his romance with Dunn on at least one occasion and even revealed that he was considering starting a family with her. Speaking to the Evening Standard when "Friends" came to an end in 2004, he shared that being a dad was "something [he thought] about a lot more now than 10 years ago," admitting he "really never considered it" when the show first began. The clearly love-struck actor candidly continued, "With Rachel in my life, I know that I can be very committed and not some selfish guy who just wants to hang out with friends. I want to spend time with my girlfriend and explore what it means to have a much closer relationship than I've previously had time for." Aww!

But this one wasn't meant to be, with Perry and the British fashion student calling it quits in June 2005. A source told People at the time, "There was no drama involved [in the breakup], just a commitment by [Perry] to stay focused on his sobriety."

Among the many famous women Matthew Perry dated was Cameron Diaz, and he shared details of their date — singular — in his memoir. According to an excerpt in Insider, he was set up with the "Charlie's Angel" star, whom he met for the first time when she arrived for a group date with mutual friends. "The date was at a dinner party with a bunch of other people, but upon seeing me, Cameron got almost instantly stoned — it was clear that she wasn't interested in me at all," Perry wrote.

During a game of Pictionary, Perry wrote, he cracked a joke to Diaz, leading her to jokingly punch him in the shoulder. "Or, at least, that's what she meant to do," Perry continued. "But she missed and, instead, punched me smack in the side of my face."

Perry then shared the pithy response he gave to her errant punch, which likely ensured there would be no second date; "Are you f***ing kidding me?" he told her.

Matthew Perry's longest romance to date happened with actor Lizzy Caplan. The two were together for a pretty long stretch, six years between 2006 and 2012, and their split appeared to come as a surprise to fans. Fans will probably best know Caplan for playing Janice Ian in "Mean Girls," while she's also appeared in "True Blood," "New Girl," and "Masters of Sex." But despite both having high-profile careers, they actually managed to keep their relationship very private.

Though they seemed happy during their time together, Caplan sparked rumors things maybe weren't great between herself and her boyfriend when asked in October 2013 about the "Friends" star by The Independent. The article claimed, "Caplan will not even entertain any questions relating to her partner" and covered her ears when Perry's name was brought up. Instead, she spoke about how much she liked to live her life outside the spotlight, saying, "I can stand right next to paparazzi and I do that sometimes. I'm close with people who are far more famous, and they know how to avoid attention." It turns out, per Us Weekly, the two had actually secretly split more than a year earlier.

As for what went wrong? Well, the notoriously private couple hasn't appeared to have confirmed what happened, though a source claimed to Daily Mail that Perry supposedly "wasn't ready to make the full commitment." Caplan married Tom Riley in 2017.

In 2018, it seemed like Matthew Perry had finally found the one in Molly Hurwitz. The two seemed to go strong for around two years and, as is the norm for Perry, kept things under wraps for a good while before going public. Hurwitz officially confirmed their romance on Valentine's Day in 2020 on her private Instagram account alongside a photo of the actor (per People) — "Second year being my valentine, but his first as an Instagram influencer. HVD to my favorite," she captioned it.

But it was only three months later that In Touch claimed it was all over, with a source claiming they'd had an "amicable" breakup. That time apart didn't seem to last too long though. Fast-forward to November 2020 and Perry confirmed they were not only back together but also engaged. In a statement issued to People, loved-up Perry gushed he was "dating the greatest woman on the face of the planet" when he proposed.

But, sadly, this one didn't end well either. On June 1, 2021, Perry told People that he and Hurwitz had called it quits, saying, "Sometimes things just don't work out and this is one of them." He didn't share much more about what went wrong, but noted, "I wish Molly the best."

As the star of one of the biggest TV shows ever, it's no surprise to hear that Matthew Perry's no stranger to a gossip column. The actor has been linked to a number of big-name stars over the years, including Renée Zellweger. However, she shut down the speculation to Cosmopolitan in 2003, saying, "He's really nice and handsome, I'm not dating him ... But that's good. Let's make my list really good!"

"Gilmore Girls" star Lauren Graham was another star rumored to have gotten close to Perry, but she revealed the interesting truth in her 2016 book, "Talking As Fast As I Can." Graham explained Perry was actually a "friend who [she] almost but never exactly dated" after the two were linked in 2003. Things seemed to be amicable though, as Graham even starred alongside Perry on TV a few times, including in "The Odd Couple" – as his ex-wife, no less!

Perry was also rumored to have dated Piper Perabo and Kirsten Davis — at the same time. The Mirror claimed in 2006 Perry had supposedly started seeing Perabo but was then spotted on an apparent date with Davis a few weeks later. "They looked very into each other," a source claimed of Perry and Davis, but it looks like this one probably was all just speculation. Perry was also linked to Jennifer Capriati and Elizabeth Hurley in 2002 but denied both to People.