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Friends fans will forever remember Matthew Perry as Chandler Bing. The actor died in October 2023 and left a legacy of funny quips behind him in the beloved series. Perry fans also learned more about his personal life in his memoir, Friends, Lovers, and the Big Terrible Thing. Here’s what Perry wrote about his relationship with Lizzy Caplan and subsequent intimacy issues.

Matthew Perry wrote about the intimacy issues he faced after he didn’t propose to Lizzy Caplan

Before Matthew Perry’s failed engagement, he dated fellow actor Lizzy Caplan for nearly six years. The actors started dating in 2006 after Perry crashed Caplan’s 23rd birthday party. They were both notoriously private about the relationship, but Perry explained more about what was happening behind the scenes in his memoir, Friends, Lovers, and the Big Terrible Thing.

Perry had a plan for getting down on one knee for Caplan. He paid an artist to create a work that showed himself and Caplan along with nearly 2,000 of their text messages, and he gave this to Caplan as a Christmas gift. Along with the present, Perry planned to propose. But the proposal never happened.

“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,'” Perry wrote, according to The Mirror. “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!'”

Perry couldn’t say why he backed out of the proposal plan. He admitted that after that Christmas, he had difficulty getting intimate with Caplan. While the two went to couple’s therapy, it didn’t help.

Lizzy Caplan, the ex-girlfriend of Matthew Perry, at a movie premiere in 2023
Lizzy Caplan | Axelle/Bauer-Griffin/FilmMagic
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He wrote more about his impotence in his memoir

Matthew Perry’s failed romance with Lizzy Caplan wasn’t the only time he described having intimacy issues in his memoir. He wrote about how his heavy drinking affected his impotence.

“Back in Ottawa, before I’d left, a girl had tried to have sex with me, but I was so nervous that I drank six beers beforehand and couldn’t perform,” he wrote, according to the New York Post. “By then, I’d been drinking for a few years. I failed to make the correlation between the booze and my private parts not working.”

Perry felt great shame. “No one could know about this — no one,” he continued. “So, I was walking around the planet thinking sex was something for other people.”

Perry’s issues improved after dating Tricia Fisher, Carrie Fisher’s half-sister. But the Friends star dumped Tricia. “She didn’t abandon me, but old fears crept up, and I ended the relationship,” he wrote.

The ‘Friends’ star later proposed to Molly Hurwitz, but their relationship ended

Matthew Perry and Lizzy Caplan didn’t work out, as stated previously, but he eventually got down on one knee for another woman — Molly Hurwitz. The two started dating in 2018, and Perry popped the question in 2020. Unfortunately, he called off his engagement in 2021.

It’s unclear exactly what caused the end of the relationship. But Perry had a well-known history of cold feet. “He’s crazy in love, but he’s scared of messing up a good thing by making things official,” a source told OK! Magazine, noting that he “worries about what kind of husband he’ll make” due to his past addiction issues.

How to get help: In the U.S., contact the Substance Abuse and Mental Health Services Administration helpline at 1-800-662-4357.

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