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Friends fans are grieving the death of Chandler Bing star Matthew Perry. Perry had a history of drug and alcohol abuse and relationships that didn’t last. Many fans know he dated fellow actor Lizzy Caplan for years, though, like the star’s other romances, it ended. Here’s what ultimately caused Perry and Caplan to break up, according to a source.

An insider alleged that Matthew Perry wasn’t ready to commit to Lizzy Caplan, causing their breakup

Lizzy Caplan looking over her shoulder at a red carpet event
Lizzy Caplan | Christopher Polk/NBC/NBCUniversal via Getty Images
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Julia Roberts Had a ‘Look of Confusion’ When Matthew Perry Dumped Her

Matthew Perry’s relationship with Lizzy Caplan spanned six years, which is no easy feat when you’re in the limelight. The couple managed to keep their low-profile romance private, as neither of them took to the tabloids to discuss dating or future plans.

Perry reportedly connected with Caplan when he crashed her 23rd birthday party, and their initial fling turned into a full-fledged relationship in 2006. Unfortunately, by 2012, Perry and Caplan were ready to call it quits. An insider told Daily Mail that Perry had trouble committing to Caplan, resulting in the breakup.

 “He wasn’t ready to make the full commitment, so they split,” the insider alleged in 2013.

“For the last year that they were together, it was very up and down, a lot of back and forth,” the source continued. “It was hard for them to let go, but ultimately, Lizzy decided she wanted more. Maybe Matthew just didn’t want to marry Lizzy, or maybe he never wants to get married at all. I don’t know, but I do know it was an issue for them. They’re both decent people. I don’t think the split was ugly.”

While Perry wasn’t ready to marry Caplan, he wrote in his memoir, Friends, Lovers, and the Big Terrible Thing, that he had plans to propose with custom-made artwork for Christmas. But he never followed through, putting strain on their relationship.

“My plan was to give her the painting and then ask the question … well, I never asked it,” he wrote. “I gave her the present and she was really moved by it, saying, ‘Matty, my little heart — what you’re doing to my little heart.’ And it was time, all I had to do was say, ‘Honey, I love you. Will you ….’ But, I didn’t say it. All my fears reared up like a snake. I immediately went into Chandler [expletive] Bing mode. ‘Hey, hey, hey!’ I said to her consternation, ‘Look at this!'”

Matthew Perry said he wasn’t ‘afraid’ of love anymore’ in 2022

Friends star Matthew Perry wasn’t ready to marry Lizzy Caplan — but in 2022, he announced that he was prepared to find lasting love.

“That was me afraid,” Perry told People regarding his past failed romances that he ended out of fear. “That is what I manifest, something that’s wrong with them. And then I break up with them. But there can’t be something wrong with everyone. I’m the common denominator. I left first because I thought they were going to annihilate me.”

“I’m going to learn as I go,” he continued. “The thing that’s changed about me is I have no interest in hanging out with somebody that I don’t know or somebody that I’m not that into. The next person I really take seriously is somebody that I’m going to be in love with and not be scared by the things that used to scare me.”

Perry also mentioned that he felt he’d make an excellent father, and he was ready to take that next step in his life. “I think I’d be great. I really do,” he said.

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