Matthew Perry almost asked Lizzy Caplan to marry him — ‘never’ spoke again after ‘harsh’ email

Matthew Perry seemingly never spoke to ex Lizzy Caplan again following their 2012 split. The “Friends” alum made the admission in his 2022 memoir, “Friends, Lovers, and the Big Terrible Thing,” which hit shelves a year before his death.

Though Perry doesn’t name Caplan by name in the book, several references point to the actress.

The pair initially met when Caplan was 23 and the “Fools Rush In” actor was 36.

“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),” he recalled. “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?’”

Perry and Caplan, now 41, would go on to be spotted at a few events, but otherwise stayed very private about their status. After two years of friends with benefits, they decided to make it official.

“[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,” he continued. “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.”

At one point, however, Perry was close to making it permanent. He decided he was going to propose, but backed out last minute.

At Christmas, he paid “a huge amount of money” for an artist to paint the two of them. Due to their relationship the first four years being “both sex-and-text driven,” he found out from his business manager they had texted “something like 1,780” times. So he asked the artist to draw that amount of hearts next to her reading a copy of the “New York Times” with bottled water as Perry was drawn in a long-sleeve shirt holding a Red Bull and a “Sports Illustrated.”

“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.”

Years later, the “Mean Girls” star would marry husband Tom Riley in May 2016. That same year, Perry invited her to see him in 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 penned.

He added: “‘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.”

According to Perry, that was the last time they ever interacted.

“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 penned.

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