Matthew Perry’s Dating History: Julia Roberts, Lizzy Caplan, Neve Campbell and More

26.10.2022 - 02:51 / usmagazine.com

Matthew Perry is no stranger to high-profile romance — but he’s still searching for “The One.”

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.

“If you have dinner with someone and the next day the country thinks you’re in a relationship, it gets a little weird,” he told Entertainment Weekly in 1997. “I was confused about dating before Friends. This all just makes it more confusing.”

In 2004, Perry described himself as “just awful with women,” telling Dateline that not being “comfortable with any silence” made for a tense moment with love interests. “I have to break any awkward moment or silence with a joke,” he quipped.

Friends, however, did lead Perry to a few big loves throughout his time on the show. In 1995, the Fools Rush In star began dating Julia Roberts after the Oscar winner made a guest appearance on the comedy series.

“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, per the U.K. paper The Times, “Let me say that again — she would only do the show if she could be in my story line. (Was I having a good year or what?) But first, I had to woo her.”

The Massachusetts native later sent the Pretty Woman star three dozen roses along with a note expressing his excitement about the possibility of her appearing on the sitcom. “Her reply was that if I adequately explained quantum physics to her,” she’d agree to be on the show,” he recalled, before