Here's What Matthew Perry Had to Say About His Dating History in His Memoir

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.

Tricia Fisher
Getty | Barry King

Tricia Fisher

Perry dated Fisher, the half-sister of Carrie Fisher, when he was 18. In the memoir, he revealed that the pair tried to wait to take their physical relationship to the next level in the early stages, but that didn't last too long.

"My firmness, at least in my conviction to wait, lasted two months . . . The make-out sessions that didn't lead anywhere were beginning to cause both of us to hyperventilate," he wrote, adding that Fisher made the first move.

The pair broke up but eventually rekindled their relationship. "Years later, Tricia and I would date again, while Friends was at its peak," he wrote. "She didn't abandon me, but old fears crept up, and I ended the relationship."

Gabrielle Allan
Getty | David Livingston

Gabrielle Allan

Perry mentioned dating "Veep" producer and writer Allan in his memoir, and though he didn't clarify the exact dates they were together, he did say their relationship led him to realize he had an issue with alcohol. "Love of alcohol had indeed become the helmsman of my life, but I don't think I realized just how much it controlled me until one night when I was out with my girlfriend at the time, Gaby."

He recalled coming home to Allan's house when he was 21 after seeing a magic show and realizing just how badly he wanted a drink. "Gaby didn't have any alcohol at home, which is, of course, totally fine, but for me at the age of twenty-one, all of a sudden this creeping feeling came over me for the first time. I felt my blood on fire for more to drink," he wrote.

Julia Roberts
Getty | Getty Images

Julia Roberts

Perry and Roberts began dating in 1995, around the time when Roberts prepared to guest star on "Friends." But Perry's insecurities led him to break up with her.

"Dating Julia Roberts had been too much for me," he wrote. "I had been constantly certain that she was going to break up with me. Why would she not? I was not enough; I could never be enough; I was broken, bent, unlovable. So instead of facing the inevitable agony of losing her, I broke up with the beautiful and brilliant Julia Roberts."

Jamie Tarses
Getty | Fiona Goodall

Jamie Tarses

Perry dated late network executive Tarses, who helped develop "Friends" back in 1994. He's never clarified the exact dates of their relationship, though he did describe her in his memoir as "the most magical, beautiful, and smart" woman. He also detailed some of what she had to do to help him with his addiction. "I called my sort-of girlfriend at the time, the wonderful Jamie Tarses, and managed to say, 'There's something wrong,'" Perry wrote, describing an experience in 2000 when he was diagnosed with pancreatitis. "Jamie was an angel from God — she drove straight over to my house, poured me into a car, and drove me to the nearest hospital."

Perry ended up breaking up with Tarses after getting sober. "I need time to process being sober," he wrote. "In order to adequately pay sweet Jamie back for two years of giving up huge portions of her own very busy and important life by basically being my nurse, I ended our relationship."

Rachel Dunn
Getty | Gregg DeGuire

Rachel Dunn

Perry dated fashion student Dunn from 2003-2005, describing her as "the ex-girlfriend of his dream" in the memoir.

When they broke up, a source told People, "There was no drama involved (in the breakup), just a commitment by Matthew to stay focused on his sobriety."

Lizzy Caplan
Getty | Leon Bennett

Lizzy Caplan

Perry dated Caplan, who played Janis in "Mean Girls," from 2006-2012. In his memoir, he wrote that he regrets their breakup. "All my fears reared up like a snake," he wrote. "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."

Molly Hurwitz
Getty | Frederick M. Brown

Molly Hurwitz

Perry dated literary manager Hurwitz from 2018 to 2021, and the pair even got engaged in 2020, per People. But they called off their engagement, with Perry telling the outlet, "Sometimes things just don't work out and this is one of them. I wish Molly the best."