Julia Roberts, Lizzy Caplan, Extra

Matthew Perry is not any stranger to high-profile romance — however he’s nonetheless trying to find “The One.”

Whereas the Mates alum would finally go on up to now his fair proportion of well-known celebrities, Perry was vocal in regards to the struggles of sustaining a relationship within the highlight following the success of his NBC sitcom, by which he starred as Chandler Bing from 1994 to 2004.

“In case you have dinner with somebody and the subsequent day the nation thinks you’re in a relationship, it will get somewhat bizarre,” he instructed Leisure Weekly in 1997. “I used to be confused about courting earlier than Mates. This all simply makes it extra complicated.”

In 2004, Perry described himself as “simply terrible with girls,” telling Dateline that not being “snug with any silence” made for a tense second with love pursuits. “I’ve to interrupt any awkward second or silence with a joke,” he quipped.

Mates, nonetheless, did lead Perry to some massive loves all through his time on the present. In 1995, the Fools Rush In star started courting Julia Roberts after the Oscar winner made a visitor look on the comedy sequence.

“Julia had been provided the post-Tremendous Bowl episode in season 2 and she or he would solely do the present if she could possibly be in my story line,” Perry wrote in his 2022 memoir, Mates, Lovers and the Massive Horrible Factor, per the U.Okay. paper The Instances, “Let me say that once more — she would solely do the present if she could possibly be in my story line. (Was I having a great 12 months or what?) However first, I needed to woo her.”

The Massachusetts native later despatched the Fairly Girl star three dozen roses together with a word expressing his pleasure about the potential of her showing on the sitcom. “Her reply was that if I adequately defined quantum physics to her,” she’d comply with be on the present,” he recalled, earlier than revealing that he went on to study every little thing he might about quantum mechanics. “The next day, I despatched her a paper all about wave-particle duality and the uncertainty precept and entanglement, and solely a few of it was metaphorical.”

Perry shared that Roberts not solely agreed to do the present, “but additionally despatched me a present” – bagels. “I did let her in, each figuratively and actually, and a relationship started. We’d already be a pair by the point we began filming the Mates Tremendous Bowl episode,” he mentioned.

Regardless of their instantaneous chemistry, the pair referred to as it quits simply two months into courting, with Perry attributing the cut up to his insecurities. “Relationship Julia Roberts had been an excessive amount of for me. I had been always sure that she was going to interrupt up with me,” the Studio 30 on the Sundown Strip alum wrote in his e book.

Following his breakup with the Oceans Eleven actress, Perry entered a number of brief flings earlier than discovering love once more with Lizzy Caplan in 2006. The Odd Couple alum and the Imply Women star dated for six years earlier than Us Weekly confirmed the twosome had cut up in October 2013.

5 years later, rumors swirled that Perry had sparked a romance with Molly Hurwitz. Us completely revealed the pair have been courting in January 2020. In November of that very same 12 months, Perry confirmed that he had proposed to the expertise supervisor.

The next month, a supply instructed Us that Perry’s inside circle — particularly former costar Courtney Cox — have been thrilled that the Emmy nominee had determined to quiet down.

“They hope he and Molly go the gap. Molly prefers nights in his non-public cinema watching movies and consuming home-cooked meals than going out,” the insider mentioned on the time. “She introduced him to a spot the place he’s constructive and assured. No person can bear in mind seeing him this glad. He’s bought a spring in his step that wasn’t there earlier than.”

Hurwitz later took to social media to rejoice her love for the Ally McBeal alum on Valentine’s Day, writing through Instagram: “Second 12 months being my valentine, however his first as an Instagram influencer. HVD to my favourite,” she captioned a candy snap of the pair in February 2021.

Six months after the actor bought down on one knee, nonetheless, the twosome referred to as it quits.

“Typically issues simply don’t work out and that is considered one of them,” Perry’s rep instructed Us in a June 2021 assertion. “I want Molly the very best.”

Hold scrolling for extra of Perry’s courting historical past through the years: