The proposal moment that never happened came after Matthew Perry gave Lizzy Caplan a custom painting that he’d commissioned of the two of them for Christmas. Perry wrote in his memoir that, “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.'”

But instead of popping the question, he said he reverted to a more Chandler Bing response to distract from the emotion of the moment. And it seems like that was the beginning of the end for their romantic relationship, with them finally separating two years after that. Along with Caplan, Perry had a number of famous exes, including Julia Roberts and Lauren Graham. Caplan went on to marry Tom Riley, a British actor, and Perry said he found out about both her engagement and the end of their friendship via email.

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