Matthew Perry was not a stranger to high-profile romance, as the actor had his fair share of dating high-society people.
While the Friends alum would eventually go on to date his fair share of famous celebrities, Perry was vocal about the struggles of maintaining a relationship in the spotlight following the success of his NBC sitcom, in which he starred as Chandler Bing from 1994 to 2004.
Friends, however, did lead Perry to a few big loves throughout his time on the show. In 1995, he began dating Julia Roberts after the Oscar winner made a guest appearance on the comedy series.
Despite their instant chemistry, the pair called it quits just two months into dating, with Perry attributing the split to his insecurities. Following their breakup, Perry entered a few short flings before finding love again with Lizzy Caplan in 2006. They dated for six years before Us Weekly confirmed their split in October 2013.
Five years later, rumors swirled that Perry had sparked a romance with Molly Hurwitz. Us exclusively revealed the pair were dating in January 2020. In November of that same year, Perry confirmed that he had proposed to the talent manager.
Six months after the actor got down on one knee, however, the twosome called it quits.
In October 2023, Perry died at age 54 following an apparent drowning.
Keep scrolling for more of Perry’s dating history over the years:
Gwyneth Paltrow
Perry briefly dated Paltrow in 1993 after they met during the Williamstown Theater Festival in Massachusetts that summer.
“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,” she wrote via Instagram in October 2023. “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. We stayed friends for a while until we drifted apart, but I was always happy to see him when I did.”
Julia Roberts
The Go On alum and the Ticket to Paradise star dated for several months from1995 to 1996 after Roberts was asked to appear on Friends during the post-Super Bowl episode.
“Julia had been offered the post-Super Bowl episode in season 2 and she would only do the show if she could be in my story line,” Perry wrote in his 2022 memoir, Friends, Lovers and the Big Terrible Thing. “Let me say that again — she would only do the show if she could be in my story line.”
While the Georgia native made Perry woo her – through roses and an essay on quantum mechanics — Roberts went on to make an appearance on the comedy and the pair dated for two months before Perry ended the romance due to his “own insecurities.”
Yasmine Bleeth
After Chandler Bing expressed having a crush on the Baywatch star during an episode of Friends, Perry and Bleeth sparked a romance in late 1996.
While the duo’s relationship was short-lived, Perry’s character would continue to make affectionate references to Bleeth on the comedy series throughout the years.
“That’s Yasmine Bleeth. She’s a completely different kind of chick. I love you both, but in very different ways,” Chandler tells his pet chick while the duo watch the actress on TV during a season 3 episode.
Neve Campbell
Sparks flew between the pair during the filming of their movie, Three to Tango, in 1998 and rumors swirled that the costars were dating. However, their fling was over by the time the romantic comedy premiered in June of the following year.
Maeve Quinlan
The Bold and the Beautiful alum was Perry’s first long term girlfriend while in the spotlight. The two dated from 2002 to 2003 before ultimately calling it quits.
Heather Graham
Following his split from Quinlan, Perry sparked romance speculation with the Austin Powers star, but they never confirmed their relationship.
Lauren Graham
The Gilmore Girls alum and the Whole Ten Yards actor began dating 2003 but split shortly after. However, they remained friendly over the years, even starring in Birds of America together in 2008.
Rachel Dunn
Perry dated the professional volleyball player – who was 14 years his junior — from 2003 to 2005.
Lizzy Caplan
The New Girl alum was Perry’s longest relationship. After six years together, the former couple quietly separated in 2012.
Molly Hurwitz
The Numb star and Canada native were together for four years, getting engaged in November 2020.
“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 one knee.
Six months after Perry popped the question, however, the two called it quits for good in June 2021.
“Sometimes things just don’t work out and this is one of them,” Perry’s rep told Us in a statement. “I wish Molly the best.”