Matthew Perry's romance with Mean Girls star and heartbreak as she got married

30 October 2023 , 01:15

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Matthew Perry revealed in his memoir that he almost asked Lizzy Caplan to marry him (Image: Getty Images)

It was already common knowledge that Friends star Matthew Perry, who suddenly died last night, was previously engaged to Molly Hurwitz, but fans are discovering his almost-marriage to Lizzy Caplan.

The one-line king shared the intimate details of his six-year relationship with Mean Girls star Lizzy Caplan in his memoir, Lovers and the Big Terrible Thing. Matthew never mentions Lizzy by name, but fans obviously figured out who she was. He wrote that he was "seconds away" from getting down on one knee, admitting that he had planned a giant romantic gesture.

You may be wondering why the beloved sitcom actor chose to abandon his pursuit. In the memoir, he explained how he went into his Chandler Bing persona right at the last minute.

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Matthew originally planned to propose to Lizzy on Christmas after unveiling his gift

The two had met at Lizzie's 23rd birthday party (Getty Images)

Apparently, the two met when Matthew, then 36, had crashed Lizzy's 23rd birthday party. He described how their casual relationship transformed into a loving partnership, adding that they both had "intimacy issues."

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Matthew had a huge romantic gesture planned. He was going to reveal a painting in tribute to the countless texts the two had sent to each other during their relationship. On Christmas, he paid an artist to create an artwork depicting the two and their 1,780 text messages.

Matthew admitted he had issues being physical in the relationship after his proposal attempt (Getty Images Europe)

"My plan was to give her the painting and then ask the question…well, I never asked it.," he said. "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!'"

Claiming to have "missed the moment," he wondered about what might have been. He imagined his marriage to Lizzy involving a house and two kids, asking himself why he didn't take the chance when he had it. Unfortunately, his hesitation had become a strain on the relationship.

Matthew couldn't definitively say why he had backed out. He said maybe he was too scared, broken or bent, admitting that he had a hard time being intimate with Lizzy after that Christmas. Couples therapy had proved pointless because he was still wondering why he'd "never asked the damn question." The Mean Girls star went on to marry British actor Tom Riley in 2017 after her split from Matthew, who got engaged to Molly Hurwitz in 2020.

The two called it off about 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."

She announced the news of their marriage to Matthew via email, which he described as "incredibly harsh," after he tried to see her during a stay in London for his West End play, The End of Longing. He described the theatre production as a "huge success" but Lizzy was "too busy" to attend.

"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."

After 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."

Mataeo Smith