Matthew Perry‘s memoir, “Friends, Lovers, and the Big Terrible Thing,” is full of 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’s love life is front and center alongside his revelations about his ongoing struggles with addiction.
While his “Friends” character, Chandler, is pretty much a one-woman man thanks to his relationship with Courteney Cox‘s Monica, Perry’s love life has been a bit more varied. Unfortunately, his struggles with addiction 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.