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Matthew Perry tragically passed away on Oct. 28 at the age of 54. Known for his beloved portrayal of the sarcastic Chandler Bing in TV sitcom “Friends,” his death shocked the showbiz world when it was announced by the LA Times that he had passed away from apparent drowning in his Californian home. While his legacy lives on via the immortal moments in Central Perk, Perry also released a memoir titled “Friends, Lovers, and the Big Terrible Thing” in 2022 which revealed more about his time shooting 10 seasons of “Friends,” as well as revelations about his personal life.

From his short relationship with Julia Roberts (he broke up with her because he thought she was going to break up with him) to his crush on Jennifer Aniston, Perry wrote candidly about his love life as well as his ongoing struggles with substance use disorder in the book.

While his “Friends” character, Chandler, was pretty much a one-woman man thanks to his relationship with Courteney Cox‘s Monica, Perry’s love life was a bit more varied. Unfortunately, his struggles with substance use disorder derailed a number of his relationships over the years. “Even though I considered myself not unattractive, I had terrible luck with women and that my relationships tended towards the disastrous,” he recalled telling the “Friends” creators about himself as they were creating his character.

In an Oct. 18 interview with People, he said he was always the one to end relationships. “That was me afraid. That is what I manifest, something that’s wrong with them. And then I break up with them,” he said. “But there can’t be something wrong with everyone. I’m the common denominator. I left first because I thought they were going to annihilate me.”

Ahead, see Perry’s real-life loves over the years.