He had been close to marriage twice – first with Lizzy Caplan, whom he dated secretly for six years and was "seconds away" from proposing, and then with Molly Hurwitz, to whom he doesn't remember proposing in a rehab facility.
In his memoir Friends, Lovers and the Big Terrible Thing, the late Friends actor made a candid confession about their split, which took place months after he "realised" he was engaged to Molly after becoming sober.
"I was high on 1,800 milligrams of hydrocodone when I asked her to marry me," he wrote, without naming Molly. "I had even asked for her family's blessing. Then I'd proposed, high as a kite. And on one knee."
Matthew had already purchased a solitaire diamond engagement ring on a gold band, stating he "was desperate that she would leave me."
He admitted that once he had left rehab and Molly moved into his LA home with her dogs, she had to remind him about his proposal, which reportedly "hurt" to perform.
"I was slowly beginning to realize that I was engaged, lived with a woman and two dogs. Needless to say, I was not ready for any of this. You live with me? We live together?" he recalled, stating Molly replied: "You went down on one knee to propose, which really hurt your stomach, remember?"
Matthew added: "Needless to say, we broke up."
The actor and the literary talent manager began dating in 2018 and he confirmed to People magazine that they were engaged in 2020. The famous actor told the outlet: "I decided to get engaged. Luckily, I happened to be dating the greatest woman on the face of the planet at this time."
However, their engagement lasted just seven months before Matthew revealed they had split, just days after the Friends Reunion episode aired. In a short statement to People, he said: "Sometimes things just don’t work out, and this is one of them. I wish Molly the best."
Molly had kind words to share after hearing the news that Matthew had been found dead in his hot tub on Saturday.
"He would have cherished the world discussing his immense talent, and indeed, he was exceptionally talented," Molly began, adding: "Our mutual respect for humor was a bond between us."
Speaking about her feelings for the actor, she continued: "Though I loved him with an intensity I couldn't articulate, he was a complex soul who, at times, caused profound pain.
"No one in my adult life has influenced me more deeply than Matthew Langford Perry. I'm profoundly grateful for everything our relationship taught me."