Matthew Perry almost proposed to Lizzy Caplan but ‘went into Chandler Bing mode’ and ‘missed the moment,’ memoir said

Matthew Perry never spoke to Lizzy Caplan again after the pair parted ways back in 2012, the Friends star admitted in his 2022 memoir Friends, Lovers, and the Big Terrible Thing. Perry did not directly refer to Caplan by name, but references suggest it was her. Caplan was 23 and Perry 36 when they first met. 

Perry died by apparent drowning on October 28. He was discovered dead in the hot tub of his home in the Pacific Palisades neighbourhood just after 4 pm.

“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),” Perry recalled in the memoir. “When we were done, I said, ‘I’m gettin out of the car now. Mostly because I’m thirty-six.’

“So began two years of probably record-breaking amounts of sexual intercourse, with no strings attached, both of us following the friends-with-benefits rule to a tee,” he continued. “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?'”

While Perry and Caplan were seen together at a few events, they mostly kept their relationship private, until they decided to make it official two years later. “[It] had morphed into love. This was one of the most ‘normal’ periods of my life. True, occasionally I’d have little slips, taking maybe two OxyContin, from which I’d then have to detox for six days,” Perry wrote. “But the relationship had deepened to the point where there was now a question I urgently needed to ask her.”

“One day, I said, ‘I think we should stop kidding ourselves. We love each other,’ and she didn’t disagree. I did love her, very much,” he wrote. “That said, our intimacy issues are being sidestepped by the fact that we were both really into working. My fear of her leaving was still deeply in place, too, and who knows, perhaps she was scared of me leaving her.”

How Matthew Perry ‘missed the moment’

Perry decided to propose to Caplan at one point, but avoided it at the last minute. He paid “a huge amount of money” to an artist and asked them to paint him and Caplan. He instructed the painter to draw multiple hearts beside her picture, which showed her reading a copy of the New York Times and holding bottled water. Perry was drawn holding a Red Bull and an issue of Sports Illustrated, wearing a long-sleeve shirt.

“I loved this woman, and I wanted her to know it,” he wrote. When he presented the gift he said “will you…” but then “immediately went into Chandler f – – king Bing mode” and “missed the moment.”

Caplan married Tom Riley in 2016, the same year that Perry invited her to watch his play The End of Longing in London. “The woman I’d dated for six years was, by now, dating a British guy, and they were spending half the year in London, the rest in Los Angeles. We were still friendly enough that we’d had a couple of lunches and texted a few times. Knowing that she was in London, I’d invited her to see ‘The End of Longing,’ but she’d texted back that she was way too busy,” Perry wrote.

“‘I’ll see you Stateside!’ she wrote. I replied that I was a little hurt that she couldn’t make it — the play was being performed in her town, for God’s sake — and then a while later I got back an email telling me that she was getting married and that she had no room in her life for friends,” he added.

Perry said that was the last contact he had with Caplan. “I never replied to that email, and we’ve never spoken since. It was an incredibly harsh way to reveal the news that she was getting married, and not something that I would ever do to a person, but there you have it,” he wrote.

“Even still, I will forever be planted in her former. I’m glad she got married and that she’s happy,” he added. “I want nothing but the best for her, forever.”