Why Matthew Perry's Proposal To His Ex Molly Hurwitz Wasn't Ideal

This article includes mentions of substance misuse.

Chandler Bing had one of the most romantic proposals on "Friends," accompanied by candles and a sweet speech to Monica Gellar. However, Matthew Perry, who played Chandler, didn't have as dreamy of a proposal in real life.

Perry began a whirlwind romance with literary manager Molly Hurwitz in 2018, per Page Six. However, the couple's relationship was kept largely out of the spotlight, and many didn't even know they were together until two years after they started dating when Hurwitz posted Perry for Valentine's Day. In a now-deleted post, Hurwitz teased Perry, who at the time recently joined Instagram. She wrote, "Second year being my valentine, but his first as an Instagram influencer. HVD to my favorite." After going Instagram official in early 2020, Perry and Hurwitz's relationship took off. Just months later, they shocked everyone when they revealed they had gotten engaged.

In November 2020, the "Friends" actor got down on one knee and proposed to Hurwitz. He shared with People, "I decided to get engaged. Luckily, I happened to be dating the greatest woman on the face of the planet at this time." Perry didn't spill any details on how he proposed or Hurwitz's reaction, but there might have been a reason why he kept it under wraps. Apparently, the actor's proposal wasn't as romantic as one may think.

Matthew Perry was as vulnerable as it gets when he released his 2022 memoir, "Friends, Lovers, and the Big Terrible Thing." From his drug and alcohol addiction to his romantic past, Perry was willing to share it all, and one thing he discussed was his not-so-ideal proposal to Molly Hurwitz.

Although the "Friends" actor painted a pretty picture with People when revealing his engagement and calling Hurwitz the "greatest woman," the proposal wasn't as nice as it seemed. According to Page Six, Perry revealed in his memoir, "I bought her a ring because I was desperate that she would leave me. I didn't want to be this injured and alone during COVID." Although he was proposing for all the wrong reasons, that wasn't the only thing wrong with the engagement. The actor shared, "I was high on 1,800 milligrams of hydrocodone when I asked her to marry me. I had even asked for her family's blessing." Perry revealed he was "high as a kite" when he got down on one knee. The actor claimed that Hurwitz knew he was on drugs when he popped the question, but she still said yes.

Hurwitz rocked her engagement ring while out with Perry in the coming months, but the engagement bliss would only last so long because the couple eventually broke up.

Less than a year after getting engaged, Matthew Perry and Molly Hurwitz called off their engagement. The "Friends" actor broke the news of the split to People, he said in a statement, "Sometimes things just don't work out and this is one of them. I wish Molly the best." At the time, Perry didn't divulge the details on why his and Hurwitz's relationship fell apart and instead shared the real reason in his memoir, "Friends, Lovers, and the Big Terrible Thing."

After revealing he was "high" when he popped the question to the literary manager, in the days after, Perry began to realize what a big commitment he made, per Page Six. He shared, "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." Because of how inebriated he was off the pills, Perry couldn't even recall the engagement. He shared, "I didn't remember — needless to say, we broke up."

Despite their difficult engagement and breakup, Hurwitz did share a touching tribute to the actor following Perry's sudden death. She wrote on Instagram, "No one in my adult life has had a more profound impact on me than Matthew Langford Perry. I have tremendous gratitude for that, for everything I learned from our relationship."

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