Revealing Details About Matthew Perry’s Sad Love Life

Actor Matthew Perry, who is probably better known as the character Chander Bing on the sitcom “Friends,” died on October 28, 2023. His assistant found him unresponsive in the hot tub at his home. He was 54 years old.

While he had career success during his lifetime, he did not have relationship success to the extent that he wanted. He wanted to get married. He wanted to have kids. That family life never happened for Perry; although, he did have numerous relationships throughout his life. Unfortunately for Perry, none of those relationships turned into his dream of a family.

In 2022, before the release of his memoir “Friends, Lovers and the Big Terrible Thing,” Perry talked to PEOPLE about his desire to have a family of his own. He explained that he didn’t want to be in a relationship with someone unless it was something serious. He said, “The thing that’s changed about me is I have no interest in hanging out with somebody that I don’t know or somebody that I’m not that into.” He continued, “The next person I really take seriously is somebody that I’m going to be in love with and not be scared by the things that used to scare me.”

Perry explained that he used to be scared of love, but as of 2022, he wasn’t scared of love anymore. He said, “I’m not afraid of love anymore, so the next girl I go out with better watch out.”

He was also still hopeful that marriage and kids would happen for him. As far as being a dad, he said, “I think I’d be great. I really do.” He added, “I grew up with a lot of little kids around me, and that’s probably why, but I can’t wait.”

While the “next girl” never came around before his death, there were many relationships prior to that point. He dated celebrities including Julia Roberts, Cameron Diaz, Valerie Bertinelli, Gwyneth Paltrow, and Lizzy Caplan. In his memoir, Perry blames himself for the fact that his relationships never ended in marriage. He blamed his drug and alcohol problem as well as low self-esteem.

Perry also blamed his mother for the fact that he felt like he was attracted to women who were unavailable. One of the women he was attracted to was Jennifer Aniston. Three years before they worked together on the sitcom “Friends,” Perry asked Aniston out, and she turned him down.

While dating Roberts, he explained that he felt like he wasn’t good enough for her and expected her to break up with him, so he ultimately broke up with her.

Perry seemed to consider Caplan the one who got away. He explained that he was too scared to propose to her, but he sometimes wonders what life would have been like if he’d been brave enough to pop the question. He wrote, “I often think if I’d asked, now we’d have two kids and a house with no view…Instead, I’m some shmuck who’s alone in his house at fifty-three, looking down at an unquiet ocean.”

The only woman Perry ever did propose to was literary agent Molly Hurwitz. He explained in his memoir that he was so high when he proposed that he didn’t even remember the proposal, yet Hurwitz still said “yes.”

Watch the video below to learn more details of Perry’s tragic love life.