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      • Matthew Perry and Lizzy Caplan had a longstanding relationship of nearly six years. They began dating in 2006 when Perry crashed her 23rd birthday party. They went on to date until 2012. While Perry planned on getting down on one knee for Caplan, he never did, which may have played into the demise of their romance.
  1. Dec 9, 2023 · Caplan started her relationship with her now husband Tom Riley in 2015, a few years after her breakup with Perry. They were engaged in 2016 and married in 2017. Riley and Caplan became parents in 2021.

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  3. Oct 30, 2023 · While reports suggest Perry hoped to have a wife and kids someday, he never married — though he considered engagement with his longtime girlfriend and fellow actor, Lizzy Caplan. Here’s what ...

    • Lauren Weiler
    • Senior Writer
  4. Aug 2, 2022 · Matthew Perry met Lizzy Caplan while he was filming Aaron Sorkin's "Studio 60 on the Sunset Strip" in 2006, which was being shot near where the "Mean Girls" star was filming the CBS' sitcom...

  5. Nov 15, 2022 · 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....

  6. Matthew Perry planned to propose to Lizzy Caplan before their split, but their relationship ended abruptly and they never spoke again.

  7. Oct 31, 2023 · Matthew Perry’s relationship with Lizzy Caplan spanned six years, which is no easy feat when you’re in the limelight. The couple managed to keep their low-profile romance private, as neither of...

  8. Nov 16, 2022 · Matthew Perry — who died at age 54 on Friday October 27 — was very candid about his personal relationships in his memoir, Friends, Lovers and the Big Terrible Thing, including his very private...