From brief flings with Gwyneth Paltrow and Julia Roberts in the ’90s to a failed engagement with Molly Hurwitz in the 2020s, Matthew Perry dated several women inside and outside Hollywood.
The “Friends” star candidly discussed the biggest loves of his life — as well as his struggles with addiction — in his memoir, “Friends, Lovers and the Big Terrible Thing,” which was released one year before his untimely death in October 2023 at the age of 54.
Take a look back at everyone Perry was romantically linked to through the years on his quest to find “The One.”
Gwyneth Paltrow
1994
In his book, Perry described having a brief “makeout session in a closet” with Gwyneth Paltrow the summer before “Friends” premiered in 1994.
The actress later shared that she had met Perry at the Williamstown Theatre 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. 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. 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,” she wrote on Instagram.
“We stayed friends for a while until we drifted apart, but I was always happy to see him when I did.”
Julia Roberts
1995-1996
Perry had his first high-profile relationship with none other than Julia Roberts.
The sitcom star said he and the “Pretty Woman” star started dating around the time she made a cameo in a 1995 episode of “Friends,” but he broke things off after just two months because he felt like he would “never be enough” for her.
“Dating Julia Roberts had been too much for me. I had been constantly certain that she was going to break up with me,” Perry wrote in his book, noting that he felt Roberts was “slumming it” by dating him.
Yasmine Bleeth
1996
Sometimes life imitates art: Perry’s “Friends” character, Chandler Bing, had a crush on Yasmine Bleeth following her turn in “Baywatch,” and the pair eventually dated in real life.
Their short-lived romance took place in 1996, but Chandler continued to make several references to Bleeth in future seasons of the beloved NBC series.
Neve Campbell
1998
Perry made a habit out of dating his co-stars in the ’90s when he began seeing his “Three to Tango” scene partner Neve Campbell.
The couple became close while filming the movie in 1998. However, they called it quits before the rom-com even hit cinemas the following year.
Maeve Quinlan
2002-2003
The “Whole Nine Yards” actor had his first serious relationship with soap star Maeve Quinlan.
The “Bold and the Beautiful” alum, who portrayed Megan Conley for over 10 years, was linked to Perry from 2002 to 2003.
It’s unclear what caused their split, though fans believe the former couple ended on good terms, as they posed together at a charity event in 2006.
Lauren Graham
2003
Perry was linked to “Gilmore Girls” star Lauren Graham in 2003, but he was single again just a few months later.
It seems there was no bad blood between the pair, as they reunited several times and even appeared in the indie movie “Birds of America” together in 2008.
Rachel Dunn
2003-2005
Perry moved on with professional volleyball player Rachel Dunn in 2003.
The athlete made several public appearances with the Emmy nominee and was dating him when “Friends” came to an end.
Unlike most of his relationships, which he famously keeps under wraps, Perry spoke publicly about his time with the former fashion student.
“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,” he gushed to the Evening Standard in 2004.
Lizzy Caplan
2006-2012
Perry dated “Mean Girls” star Lizzy Caplan for six years, making their romance his longest to date.
The Massachusetts-born actor began dating Caplan in 2006, and the two managed to keep their relationship largely out of the spotlight.
Read more about Matthew Perry’s life and struggles:
- 55 Vicodin & a quart of vodka: The most shocking tales from Matthew Perry’s tell-all memoir
- Matthew Perry: How to tell which drugs I used during ‘Friends’
- Matthew Perry reveals why he broke up with Julia Roberts in the ’90s
- Matthew Perry claims Cameron Diaz once punched him in the face on secret date
- Matthew Perry, Valerie Bertinelli made out while Eddie Van Halen was passed out
Rumors of trouble in paradise first arose in 2013 when the Independent claimed Caplan would “not even entertain any questions relating to her partner” during an interview and even covered her ears when his name was mentioned.
“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,” she told the outlet.
It turns out, Perry and the “Masters of Sex” alum had secretly split one year prior.
Molly Hurwitz
2018-2020
Perry started dating literary manager Molly Hurwitz in 2018.
Hurwitz did not confirm their relationship until 2020 when she paid tribute to the “17 Again” star on Valentine’s Day.
“Second year being my valentine, but his first as an Instagram influencer. HVD to my favorite,” she captioned an Instagram post.
Flash-forward to November of that year, and Perry revealed he had popped the question.
“I decided to get engaged. Luckily, I happened to be dating the greatest woman on the face of the planet at this time,” he gushed to People after getting down on bended knee.
Six months later, however, the two called off their engagement.
“Sometimes things just don’t work out, and this is one of them,” Perry’s rep said in a June 2021 statement. “I wish Molly the best.”
