Throwback/ When Matthew Perry said 'We can't be friends' to crush Jennifer Aniston

Matthew Perry once opened up about his "serial crush" on one of his co-stars, Jennifer Aniston. During The Diana Sawyer Interview, Perry disclosed how his feelings for Jennifer Aniston, who played Rachel Green on the sitcom, went beyond friendship. The actor's revelations shed light on the dynamics behind the scenes and the enduring camaraderie among the Friends cast.

Matthew Perry's encounter with Jennifer Aniston

Matthew Perry's memoir delves into his encounters with Jennifer Aniston long before they became household names on Friends. During an interview with Entertainment Weekly, Perry recounted how he met Aniston through mutual acquaintances approximately three years prior to the start of the hit show. 

The actor candidly expressed his immediate attraction to Aniston, which set the stage for a friendship that would soon evolve into something more. He said, "I was immediately taken by her (how could I not be?) and liked her, and I got the sense she was intrigued, too — maybe it was going to be something."

Matthew's crush on his co-stars

During an interview with Diane Sawyer, Perry did not shy away from addressing his "serial crush" on not only Jennifer Aniston but also his other "Friends" co-stars, Courteney Cox and Lisa Kudrow. He stated matter-of-factly, "Well, how can you not have a crush on Jenny? And Courteney [Cox]? And Lisa [Kudrow]?"

Perry's book, "Friends, Lovers, and the Big Terrible Thing," also delves into the awkwardness he experienced when working with Jennifer Aniston. He humorously recalled wondering how long he could look at the gorgeous Jen without making it uncomfortable. In one passage of the book, he writes about Jennifer Aniston letting him do just that, which became a topic of gratitude for him.

Matthew Perry's regrettable proposition

Matthew Perry shared a humorous yet somewhat regrettable incident from his past. He acknowledged that his crush on Jennifer Aniston led him to make an ill-fated proposition. At one point, he asked Aniston out, which she politely declined. This proposition seemed to complicate their budding friendship, with Perry admitting, "I compounded the error by then asking her out." Aniston's response? She expressed her desire to be friends, to which Perry responded with, "We can't be friends!"