Highlights
- In his memoir, Matthew Perry shared that his date with Cameron Diaz went wrong when Diaz accidentally hit him in the face during a party game.
- Mattew Perry also revealed sweet details about his relationship with Julia Roberts, saying he ultimately broke up with her because he thought she would end the relationship.
- The late Friends actor also mentioned his flings with Gwyneth Paltrow, Neve Campbell, Lauren Graham, Yasmine Bleeth, and a secret make-out session with Valerie Bertinelli.
Matthew Perry's night out with Cameron Diaz didn't go to plan, according to the actor. The Friends star, who sadly passed away in October 2023, claimed that Diaz "accidentally hit him in the face," during an "unexpected" group date in 2007.
Perry explained he was set up with the There's Something About Mary star after the actress split up with Justin Timberlake. "Years ago, right after she quit seeing Justin Timberlake, I got set up on a date with Cameron Diaz," Perry wrote in his memoir Friends, Lovers, and the Big Terrible Thing. In his book, he explained how a date went very wrong after the star got a little overexcited during a party game.
What Happened During Cameron Diaz's Date With Matthew Perry?
Matthew Perry explained in his memoir how a date with Cameron Diaz went very wrong after the actress became "stoned." Perry claimed that Diaz got “immediately stoned” during a group dinner party and “wasn’t interested in him at all." Cameron Diaz had been dating Timberlake between 2003 and 2007 before a very public split.
"But the party went on nevertheless, and at one point we were all playing a game — Pictionary, I think," Perry explained. "As she was drawing, I said something witty to Cameron, to which she said, 'Oh, come on!' and proceeded to punch me in the shoulder."
But the actress missed and actually smacked the 17 Again actor in the face. Perry explained that he was caught off guard and shocked by Diaz accidentally punching him. "'Are you f****** kidding me?' I said, realizing I'd just been punched in the face by Cameron Diaz, and my big arms hadn't helped at all," he recalled. The star previously explained he began working out around this era, and wore his sleeves rolled up to show off his muscles.
Cameron Diaz and Matthew Perry's relationship didn't go any further than this incident, and there wasn't a second date.
What Matthew Perry's Relationship With Julia Roberts Was Like
In addition to sharing details about his "romantic" interaction with Cameron Diaz, Matthew Perry also opened up in his memoir about his romance with Julia Roberts. The Friends star claimed the actors would send each other “hundreds” of faxes per day, despite their intense schedules. The pair met when Roberts was a guest star on Friends.
“Three or four times a day I would sit by my fax machine and watch the piece of paper slowly revealing her next missive,” Perry wrote in his 2022 memoir. He revealed that he would find himself at a "party sharing a flirtatious exchange with an attractive woman and cut the conversation short, so I could race home and see if a new fax had arrived. Nine times out of 10, one had.”
Perry added that the Erin Brockovich star's messages were “so smart” and he felt as if “she was placed on this planet to make the world smile”.
“The way she strung sentences together, the way she saw the world, the way she articulated her unique thoughts, all was so captivating,” he added, revealing their first phone call together lasted for five hours.
Perry explained he broke up with Julia Roberts because dating the Oscar winner was "too much for him," and he was sure she would end the relationship. “So instead of facing the inevitable agony of losing her, I broke up with the beautiful and brilliant Julia Roberts.”
More Of Matthew Perry's Famous Past Relationships
Cameron Diaz and Julia Roberts were not the only famous women Matthew Perry has been connected to. In his memoir, he opens up about several famous flings he has had over the year.
One of the famous ladies he revealed he had a fling with was Gwyneth Paltrow. In his memoir, he described their brief "make-out session in a closet" the summer before Friends was aired. After Perry passed away in October, Paltrow wrote about their summer together before they both became famous.
"He was so funny and so sweet and so much fun to be with," she recalled in an Instagram tribute to the actor. "We drove out to swim in creeks, had beers in the local college bar, kissed in a field of long grass. It was a magical summer."
“He had shot the pilot of Friends, but it had not aired yet. He was nervous, hoping his big break was just around the corner. It was. We stayed friends for a while until we drifted apart, but I was always happy to see him when I did," she added, revealing there was no dramatic break-up between the acting duo.
Matthew Perry was also linked to Neve Campbell, Lauren Graham and Baywatch actress Yasmine Bleeth.
Matthew Perry also revealed in his memoir that he had a secret make-out session with his Sydney co-star, Valerie Bertinelli, while her then-husband, Eddie Van Halen, was passed out nearby. "Valerie and I had a long, elaborate make-out session. It was happening — maybe she felt the same way I did. I told her I had thought about doing that for a long time, and she had said it right back to me."
Matthew Perry's longest relationship was with the Mean Girls actress, Lizzy Caplan, although he doesn't mention her by name in his memoir. When the couple separated in 2012, Perry writes about the break-up with great regret. "All my fears reared up like a snake," he penned. "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."
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