Matthew Perry, best known for his role as Chandler Bing in the iconic TV series “Friends,” revealed in his 2022 memoir, “Friends, Lovers, and the Big Terrible Thing,” that his relationship with actress Lizzy Caplan took an unexpected turn following their breakup in 2012. Perry’s candid memoir, which was published a year before his passing, provided insights into their whirlwind romance and the circumstances that led to their eventual separation.

While Perry did not explicitly name Caplan in his book, various references within the memoir suggest that he was referring to the actress. Their story began in 2010 when they first crossed paths, with Caplan being 23 years old at the time and Perry, 36.

The actor recalled an early encounter, stating, “In fact, I knew she was twenty-three because I’d crashed her twenty-third birthday party. Our subsequent initial make-out session was in the back of a really messy Toyota (to think I’d spent all that money on fancy cars and here I was in the backseat of a tan Corolla).”

Their initial connection evolved into a “friends-with-benefits” relationship that lasted for two years. Perry described their arrangement, saying, “We were on the same page. We never went to dinner, we never talked about each other’s families. We never discussed what went on in each other’s lives regarding other people. Instead, it was texting, and saying things like, ‘How about Thursday night at seven?'”

Despite keeping their relationship low-key and avoiding public attention, their bond eventually deepened, and Perry realized he was in love with Caplan. He contemplated proposing, even having an artist create a painting to commemorate their relationship, featuring thousands of hearts representing their text exchanges.

However, Perry’s nerves got the best of him, and he missed the moment to pop the question. Caplan would later marry Tom Riley in 2016.

Perry invited her to see him in his play, “The End of Longing,” in London, and while she was initially receptive, she later informed him that she was too busy to attend, ultimately revealing in an email that she was getting married. This abrupt and impersonal message marked the end of their contact.

Perry confessed that he never replied to the email, and their last communication was characterized as “harsh.” Despite the ending of their romantic relationship, Perry wished her well, stating, “I’m glad she got married and that she’s happy. I want nothing but the best for her, forever.”

Matthew Perry’s memoir provided an intimate look at the ups and downs of his life and relationships, offering readers a glimpse into the actor’s personal experiences.