A Timeline Of Matthew Perry’s Dating History

Matthew Perry doesn’t seem to have had the easiest time when it comes to love. The “Friends” star has enjoyed a string of relationships in the public eye, and he’s been linked to multiple big names over the years (more to come on that one).

Perry has been notoriously private when it comes to speaking publicly about his love life and has admitted that there have been a few famous names he’s been linked to that haven’t exactly been 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 is known to have gotten cozy with a few of his co-stars (more on that later, too), 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, now that we know Schwimmer, Aniston, Lisa Kudrow, Courteney Cox, and Matt LeBlanc won’t be popping up in Perry’s dating history, let’s get down to business.

Matthew Perry and Julia Roberts dated on and off screen

The no hook-up rule apparently didn’t extend to “Friends” guest stars, as Matthew Perry’s first high-profile romance was with none other than Julia Roberts. There are some conflicting reports about how the two came to be, with some claiming they met on the set when Roberts played Chandler Bing’s love interest, Suzie, with who he went on a date — only for her to leave him high and dry naked in a restaurant bathroom. But that’s not where it all started. 

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. How specific! 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 the two would flirt with one another 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. They dated from 1995 until 1996, but the relationship fizzled. Roberts had just ended her marriage to Lyle Lovett at the time, and then went on to marry Daniel Moder in 2002.

Matthew Perry lived Chandler Bing's dream by dating Yasmine Bleeth

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!

It was an on set romance for Neve Campbell and Matthew Perry

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.

According to Who’s Dated Who though, this one 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 and it seems neither actually commented on their relationship or breakup publicly, but 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 2019.

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.

Matthew Perry and Maeve Quinlan didn't shy away from the cameras

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.

Matthew Perry and Heather Graham dated 'briefly' in the early 2000s

2003 saw Matthew Perry 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 time 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 more friendly as exes?

Matthew Perry was with British student Rachel Dunn for around two years

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 (per People), 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.”

Did Matthew Perry not want to settle down with Lizzy Caplan?

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” (per IMDb). 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 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 doesn’t appear 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.

Matthew Perry didn't stop looking for love after ending things with Lizzy Caplan

For the longest time, there was nothing to report following Matthew Perry’s top-secret split from Lizzy Caplan. The actor’s named mainly stayed out of the spotlight when it came to his romantic life, and even he appeared to admit he was growing tired of the speculation surrounding who he was dating.

In a 2013 USA Today interview, Perry made it clear he wouldn’t be speaking about who he was getting cozy with but did open up about what he’s looking for, telling the outlet, “I definitely want to have kids. So I have to get on that.” When asked directly about his love life, Perry confirmed that he’d been dating “a little bit” but would not name names. He also spoke about working on himself more and how he could relate to his character in the show “Go On.” As Perry explained, “One of the things that I find very fascinating about the character is he’s a narcissistic guy, self-centered guy, and he’s learning to come out of himself and care about others, and learning the value in that.”

But the star wasn’t exactly shunning love altogether. Kate Haralson alleged to Page Six that she’d spotted Perry on the elite dating app, Raya, in May 2020 and claimed they matched before exchanging a few messages. The report raised some eyebrows, as Haralson was 19 at the time and Perry was 51.

Matthew Perry popped the question to Molly Hurwitz but it didn't end well

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.”

Matthew Perry's career has been plagued with rumored Hollywood hook-ups

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 2010 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.

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