It's well known that Matthew Perry, who passed away at age 54 this week, was previously engaged to Molly Hurwitz, but he revealed he almost settled down with his ex-girlfriend Lizzy Caplan.
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The Friends actor opened up about his six-year relationship with the Mean Girls star in his memoir, Friends, Lovers and the Big Terrible Thing. Although he never mentions her by name, he explained he was "seconds away" from proposing – and he even had the romantic set-up planned.
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So why did Matthew and Lizzy never get married? The TV star, most widely known for his portrayal of Chandler Bing, candidly opened up about his near-miss proposal, and how he fell back on his comedic sitcom character's persona at the crucial moment.
The former couple met at Lizzy's 23rd birthday party which Matthew, then 36, had crashed. What began as a very casual relationship "morphed into love", he explained, adding they both had "intimacy issues."
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Matthew almost proposed to Lizzy during their six-year relationship
"For Christmas, I'd paid a huge amount of money for an artist to paint the two of us," he said, as he revealed the painting paid tribute to the 1,780 texts they'd sent to each other over the course of their relationship.
"My plan was to give her the painting and then ask the question…well, I never asked it. 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.'
Friends, Lovers and the Big Terrible Thing by Matthew Perry, $14.39/£12.50, Amazon
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"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," Matthew said. "I immediately went into Chandler [expletive] Bing mode. 'Hey, hey, hey!' I said to her consternation, 'look at this!'"
After adding he'd been "seconds away" but "missed the moment", he mused about the life he could have had with her – which, in his mind, included "two kids and a house" – and tried to understand why he had let the opportunity pass him by.
Lizzy and her husband Tom Riley, whom she married in 2017
"I was too scared, or broken, or bent," he said, before revealing that the almost-proposal had a huge impact on their physical relationship over the following two years. "No amount of couples therapy could explain why I'd never asked the damn question, and why now I just looked on her as my best friend only."
After their split, Lizzy went on to marry British actor Tom Riley in 2017 while Matthew got engaged to Molly Hurwitz in 2020 before calling it off seven months later. "Sometimes things just don't work out and this is one of them," Matthew said, according to People. "I wish Molly the best."
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