Matthew Perry’s Relationship History Includes Some of Hollywood’s Most Famous Women

He’s back on the market! Following Matthew Perry’s split from his most recent ex, Molly Hurwitz, he’s a single man once more. But don’t expect him to jump into a new relationship anytime soon. After his breakup from ex Lizzy Caplan, who he dated for six years, the Friends alum was single for half a decade. He didn’t always fly solo, though. Back in the late ‘90s and early 2000s, he dated plenty of Hollywood’s most famous women.

When the TV star was first working on Friends, he described himself as “not an unattractive man,” but “just awful with women” while talking to the series creators. “I also am not comfortable with any silence at all,” he said on Dateline in 2004 when he told the story. “I have to break any awkward moment or silence with a joke.”

After the show started gaining traction, however, he found himself in a series of high-profile relationships — and the source of Hollywood gossip whenever he so much as hung out with a female friend. “If you have dinner with someone and the next day the country thinks you’re in a relationship, it gets a little weird,” he joked with Entertainment Weekly in 1997. “I was confused about dating before Friends. This all just makes it more confusing … [But], worst-case scenario, I still have the best job anyone could ever ask for.”

Matthew Perry
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In his most recent relationship, he turned his attention to a woman behind the camera rather than in front of it. He and talent manager Molly privately dated for a year and a half before they were first spotted together in December 2019. In February, she confirmed their relationship online with a romantic Valentine’s Day post. “Second year being my Valentine, but his first as an Instagram influencer,” she joked after the 17 Again star joined the social media site. “HVD to my favorite.”

The duo made a good pair as Matt seemed to go through some serious turmoil. “She’s been his rock in recent months,” an insider told In Touch in January. Unfortunately, the two decided to “go their separate ways” by May. “It was very amicable,” a second source said.

Whether Matt plans to get back into the dating game has yet to be seen, but one thing we do know is he’s got plenty of experience dating Hollywood’s hottest. Check out his full dating history in the gallery below.