Fans loved Matthew Perry's humor and fumbles in Friends, but the actor missed his real proposal. All he had left was one last painful email.
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Friends actor and everyone's favorite, Chandler Bing, aka Matthew Perry, was someone who faced many ups and downs in his life. Even after achieving much fame in the 90s, he dealt with his own demons of addiction and health issues. Before he passed away, the actor had written his memoirs and mentioned unknown details about his life.
In his 2022 book, Friends, Lovers, and the Big Terrible Thing, he revealed quite a few secrets and personal moments. One such experience was related to his relationship with an ex-girlfriend, his near-engagement, and his biggest heartbreak. This was his "Chandler Bing" moment, as in he managed to fumble and ruin a good thing due to panic and uncertainty.
Before his failed engagement to Molly Hurwitz, Matthew Perry had almost proposed to another woman way back around 2012. The Friends alum met Lizzy Caplan in 2006, and it was a different kind of "meet-cute" (according to the New York Post).
