Matthew Perry admitted in his memoir, "Friends, Lovers, and the Big Terrible Thing," that he never spoke to Lizzy Caplan again after their breakup in 2012. Though he did not mention Caplan by name, there were several references in the book that pointed to her. The two initially met when Caplan was 23 and Perry was 36. Perry recalled crashing Caplan's twenty-third birthday party and their subsequent make-out session in the back of a messy Toyota.
Despite their age difference, they engaged in a two-year long "friends with benefits" relationship, strictly adhering to the rules without any emotional attachment or discussion about their personal lives. While they were occasionally seen together at public events, they kept their relationship private.
However, after two years, their relationship evolved into love, and Perry felt compelled to ask Caplan a crucial question.
He confessed his love for her, and she didn't disagree. Despite their deepening relationship, both of them were committed to their work, and their fear of abandonment persisted. Perry even considered proposing, but he backed out last minute. During Christmas, he commissioned an artist to paint a picture of them to express his love, but he missed the opportunity to propose.
In May 2016, Caplan married Tom Riley, and that same year, Perry invited her to see his play in London.
However, she declined due to her busy schedule and later informed Perry of her marriage and her desire to cut off all ties with him. Since then, they have not had any contact. Perry never responded to her email and wishes nothing but the best for her.
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