The Biggest Revelations from Matthew Perry's Memoir, 'Friends, Lovers, and the Big Terrible Thing'

Matthew Perry is opening up about the highs and lows of his time in the spotlight.

In his memoir, Friends, Lovers, and the Big Terrible Thing (released on Nov. 1), the Friends alumnus shares candid details about everything from his acting career to his high-profile relationships.

The actor also opens up about his long journey with addiction, noting he almost died a few years ago at age 49.

"I wanted to share when I was safe from going into the dark side of everything again," he tells PEOPLE exclusively in his cover story. "I had to wait until I was pretty safely sober — and away from the active disease of alcoholism and addiction — to write it all down. And the main thing was, I was pretty certain that it would help people."

From his surprising romances to the roles he almost took on, here are the biggest revelations from Perry's memoir.

His colon burst as a result of overusing prescription opioids

Perry opens his book with a frightening experience in which he was hospitalized for five months after his colon ruptured as a result of using OxyContin.

"The doctors told my family that I had a two-percent chance to live. That's the time I really came close to my life ending," Perry told PEOPLE about the terrifying experience.

After the event, Perry reveals that he went into a coma for two weeks, and when he awoke, he had a colostomy bag that he had to use for about a year.

He started drinking when he was 14

In addition to opening up about his drug addiction, Perry also talks about his addiction to alcohol, noting that he had his first drink when he was 14. He adds that his alcoholism began to get worse in high school when he first started acting.

"Acting was another one of my drugs," he writes. "And it didn't do the damage that alcohol was already starting to do. In fact, it was getting harder and harder to wake up after a night of drinking."

He lost his virginity to Tricia Leigh Fisher

In his memoir, Perry discusses many of his high-profile relationships, including his romance with Tricia Leigh Fisher, the half-sister of the late Carrie Fisher, when he was 18. He opens up about how their relationship deepened, recalling how he lost his virginity to her.

"That night, by the dint of a miraculous universe and the ministrations of a beautiful young woman who deserved better, I finally first misplaced my virginity then lost it altogether," he writes.

He was going to be in Don't Look Up

Perry reveals that he was initially going to star in Don't Look Up, but a medical scare forced him to pull out of the movie.

The actor adds that he was on 1,800 milligrams of hydrocodone while he filmed a group scene with Jonah Hill that did not make the film's final cut.

He fell "madly in love" with Valerie Bertinelli while filming Sydney

While filming Sydney, Perry says he fell "madly in love" with his costar Valerie Bertinelli, who was married to Eddie Van Halen at the time. He recalls one moment when he was at the couple's house and made out with Bertinelli while Van Halen was passed out from drinking.

Despite their interaction, the two never officially dated, as he notes that "Valerie made no mention of what had happened" the next day on set. "I quickly got the hint and also played the role I was supposed to, but inside I was devastated," he says.

Being on another show almost stopped him from booking Friends

Perry writes about the early beginnings of Friends, which was titled Friends Like Us at the time, revealing that he almost didn't get to audition for Chandler due to conflicts with another series titled L.A.X. 2194.

Thankfully for him, L.A.X. 2194 didn't end up getting picked up, making him available to audition for Friends, which he, of course, ended up booking.

He proposed to Molly Hurwitz when he was high

Though he doesn't refer to Molly Hurwitz by name, he does open up about their engagement in November 2020.

"I bought her a ring because I was desperate that she would leave me," he recalls in his memoir. "I didn't want to be this injured and alone during Covid." He also reveals that he was "high on 1,800 milligrams of hydrocodone" when he asked her to marry him.

The couple later announced their breakup in June 2021. "Sometimes things just don't work out and this is one of them," Perry said in a statement to PEOPLE at the time. "I wish Molly the best."

He once made out with Gwyneth Paltrow in a closet

Among his many dalliances, Perry reveals that he once made out with Gwyneth Paltrow in a broom cupboard during a party in Williamstown, Massachusetts, where she was doing a play and he was visiting his grandfather. "We were both still unknown enough that it didn't make it to the tabloids," he adds.

His heart stopped for five minutes during his colon surgery

After his colon burst, Perry notes that his heart stopped beating for five minutes during surgery, as a result of doctors giving him propofol. "It wasn't a heart attack — I didn't flatline — but nothing had been beating," he says.

His relationship with Julia Roberts started over fax

Perry details his high-profile romance with Julia Roberts, who appeared on season 2 of Friends, noting that "courtship had initially been conducted via fax," as they shared poems and sweet words with each other. He also reveals that Roberts "would only do [Friends] if she could be in [his character's] storyline."

He struggled with addiction throughout his time on Friends

While tracing his drug addiction, he recalls that his "Vicodin habit" kicked in badly when he was filming Friends, noting that his appearance changed drastically based on his addiction at the time.

"You can track the trajectory of my addiction if you gauge my weight from season to season — when I'm carrying weight, it's alcohol; when I'm skinny, it's pills. When I have a goatee, it's lots of pills," he writes.

Bruce Willis appeared on Friends because he lost a bet to Matthew Perry

In addition to sharing details about his time on Friends, Perry also recalls working with Bruce Willis in the 2000 film The Whole Nine Yards.

The film ended up becoming a major hit, which incidentally led to Willis' guest appearance on Friends. "Bruce hadn't been sure the film would work at all, and I'd bet him it would — if he lost, he had to do a guest spot on Friends," he wrote, adding, "(he's in three episodes of season six)."

He planned on asking Lizzy Caplan to marry him

In the memoir, Perry opens up about his private romance with longtime girlfriend Lizzy Caplan. Though he doesn't refer to the Mean Girls alumna by name, he does make several pointed references to the actress, including how they dated for six years and how she eventually married a "British guy" when he was doing his 2016 play The End of Longing in London. (Caplan married Tom Riley in May 2016 after the two met while filming in London.)

He details how his relationship with Caplan started out as "friends with benefits" before eventually morphing into love, revealing that at one point, he almost asked her to marry him.

"I didn't say it," he recalls of not popping the question. "All my fears reared up like a snake, the snake I feared was coming to get me the year before I'd met her, the time when I'd seen God but managed to learn not enough from him."

He had to re-record most of his lines for Serving Sara as a result of his drug use

As his addiction began to interfere with his work, Perry recalls being "a mess" during filming for his 2002 film Serving Sara with Elizabeth Hurley, during which he left to go to rehab for his painkiller addiction.

He reveals that he ended up having to rerecord his slurred parts for the entire movie, "which meant I looped the entire movie," he adds.

"Of course, the movie tanked anyway," he continues. "I was paid $3.5 million to do the movie and I got sued for the shutdown, even though it was a health issue. At the mediation table a team of insurance flacks faced me down, so I just wrote them a check for $650,000."

Cameron Diaz accidentally punched him in the face on a date

Perry reveals that he once got set up with Cameron Diaz following her split from Justin Timberlake. During the dinner party, he says that Diaz "got almost instantly stoned" and ended up accidentally punching him in the face as he said something witty, meaning to hit him in the arm.