One Of Matthew Perry's Final Comments About Finding Love Is Even More Heartbreaking Now

Before Matthew Perry died, he reflected on his love life in his memoir titled "Friends, Lovers, and the Big Terrible Thing." Whereas his "Friends" character, Chandler Bing, got a happy ending by marrying one of his best friends and starting a family with her, Perry's own love life was no sitcom fairytale. Some of his romance revelations in his book are downright painful, such as when he kissed his then-married "Sydney" co-star Valerie Bertinelli at her house. Upon returning to work, Bertinelli acted like nothing had happened. "I was devastated," Perry wrote.

There was also the unrequited crush on his "Friends" co-star Jennifer Aniston. He even dared to ask her out and got shut down. "She said she'd love to be friends with me," he recalled in his memoir. "And I compounded the compound by blurting, 'We can't be friends!'" 

Perry did reach the dating stage with several well-known female celebrities, including Julia Roberts, Yasmine Bleeth, Neve Campbell, and Lizzy Caplan. Unfortunately, he developed a bad habit of dumping his girlfriends. "I'm deathly afraid that they will find out that I'm not enough, that I don't matter, and that I'm too needy, and they'll break up with me and that will annihilate me and I'll have to take drugs and that will kill me," he explained to GQ. But after getting sober and pouring his heart out in the pages of his memoir, Perry was prepared to give love another chance.

For Matthew Perry, there were a lot of ones who got away. "I'm not being dramatic when I say there's 10 women on the face of the planet that I would kill to be married to," he told GQ in 2022. They were all his exes. 

That same year, Perry told People that love was something he still yearned for. The actor admitted that he'd always been the problem in his past relationships by being insecure and terrified of rejection. By reaching this realization and accepting it, he experienced some major personal growth. "Through a lot of work, I've got over that fear," he said. He was also starting to put a lot of thought into what traits would make someone his ideal partner. "A sense of humor, beautiful inside and out, caring. This is really important, somebody who can have a back and forth with me," he said. He also revealed that past experiences had made him wary of women who couldn't support themselves financially.

If he could find what he was looking for, Perry was very much ready to settle down. "I'm feeling more confident and I'm not afraid of love anymore," he said. He added that his future plans definitely included starting a family. "I think I'd be great [as a dad]. I really do ... I can't wait."

Matthew Perry revealed that he came close to marrying at least two of his exes. In "Friends, Lovers and the Big Terrible Thing," he recalls planning a proposal for one unnamed ex only to chicken out at the last minute. People identified the ex in question as "Mean Girls" star Lizzy Caplan and shared an excerpt about Perry's relationship with her. "I often think if I'd asked [her to marry me], now we'd have two kids and a house. Instead, I'm some schmuck who's alone in his house at fifty-three," Perry mused. He did pop the question to literary manager Molly Hurwitz in 2020, but their engagement was called off the following year.

Perry's relationship with "Pretty Woman" star Julia Roberts didn't progress to the point that he got down on one knee. Roberts just happened to be celebrating her 56th birthday on the day Perry died, as pointed out by the New York Post. The two actors became an item in the '90s ahead of a cameo by Roberts on an episode of "Friends." In his memoir, Perry recalled communicating with Roberts regularly by fax and ending their relationship when those old fears of rejection started creeping into his thoughts again. "Instead of facing the inevitable agony of losing her, I broke up with the beautiful and brilliant Julia Roberts," he wrote.

It was difficult for Matthew Perry to watch his former loves get married and start families because it was something he desperately desired. "They're all happy, which is great, but I'm the one who's sitting in a screening room by myself. And there's no lonelier moment than that," he told GQ in 2022. He also explained to The Washington Post why he disliked being alone, saying, "I think I'm afraid of my mind a little bit."

Perry was giving an interview to Entertainment Weekly 25 years prior when he got another chance at romance with a popular female actor. The 1997 interview was being conducted at a restaurant, and "Candyman" star Virginia Madsen had a plate of banana fritters sent over to his table. The waitress only told Perry the fritters were from someone named Virginia. He didn't read the accompanying note until the end of the interview. Once he did, he started plotting his next move. "Okay, let's see. Paying for her meal screams that I'm desperate and I'm gonna die alone," he said. Perry eventually decided to chat up Madsen and have a few drinks with her — but his interviewer observed that he was alone when he left the eatery. Although Perry's comment about the possibility of dying alone was offhand, it takes on a somber tone in retrospect.