Matthew Perry, the star of Friends, had a heartbreaking romance with Mean Girls actress Lizzy Caplan and in his memoir revealed he was "seconds away" from proposing to her.
The actor, who was tragically found dead at his Los Angeles home at age 54 after reportedly drowning in his hot tub, never mentioned Lizzy by name in his book, but fans quickly figured out who she was. He confessed that he had planned a grand romantic gesture for the proposal.
Fans might be curious as to why Matthew decided not to go ahead with his plans and in his memoir, Friends, Lovers and the Big Terrible Thing explained that he slipped into his Chandler Bing character at the last moment. Matthew also reflected emotionally on his weight loss journey due to addiction struggles.
The story of how he met Lizzy is quite interesting as Matthew, then 36, crashed Lizzy's 23rd birthday party. He wrote about how their casual relationship evolved into a loving partnership, despite both having "intimacy issues."
Matthew had planned a big romantic surprise for Lizzy as he commissioned an artist to create a painting that represented the numerous text messages they had exchanged during their relationship. The artwork, which depicted the couple and their 1,780 texts, was meant to be unveiled on Christmas.
The actor, known for his role as Chandler Bing in Friends, shared a heart-wrenching story about how he missed the chance to propose to his then-girlfriend. He said: "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.'
"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 admitted that he had "missed the moment," and wondered about what might have been. He imagined his life with Lizzy, complete with a house and two kids, and questioned why he didn't seize the opportunity when he had it – his hesitation put a strain on their relationship.
The Friends star couldn't pinpoint exactly why he backed out of the proposal. He suggested that maybe he was too scared or broken, and confessed that he struggled to be intimate with Lizzy after that Christmas.
Despite attending couples therapy, he was still left wondering why he'd "never asked the damn question." Lizzy went on to marry British actor Tom Riley in 2017 after splitting from Matthew, who got engaged to Molly Hurwitz in 2020.
However, Matthew and Molly called off their engagement around 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."
Matthew was left heartbroken when Lizzy announced their split via email, which he described as "incredibly harsh," especially after he tried to meet her while he was in London for his West End play, The End of Longing. He said the play was a "huge success" but Lizzy was "too busy" to come.
"There was one person who wouldn't come to the play, even though I begged," he wrote. "The woman I'd dated for six years was, by now, dating a British guy, and they were spending half the year in London, the rest in Los Angeles."
When she said she couldn't meet him, he added: "I replied saying I was a little hurt that she couldn't make it…and then a while later I got an email telling me that she was getting married and that she had no room in her life for friends.
"It was an incredibly harsh way to reveal the news that she was getting married, and not something that I would ever do to a person, but there you have it. I'm glad she got married and that she's happy. I want nothing but the best for her, forever."
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