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Matthew Perry Says Cameron Diaz Accidentally Punched Him on a Date

Posted on November 8, 2022

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  • Matthew Perry said he and Cameron Diaz were set up on a date after her split from Justin Timberlake.
  • Perry said while playing Pictionary at a dinner party years ago, she accidentally punched him.
  • Perry said Diaz was likely aiming for his arm but instead “punched me smack in the side of my face.”
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Matthew Perry said that he was once the recipient of an unintentional punch from Cameron Diaz.

Perry, known for his role as Chandler Bing on “Friends” said that he crossed paths with the actress approximately 15 years ago following her split with Justin Timberlake.

Diaz and Timberlake dated from 2003 to 2007 and costarred in two movies: the animated film “Shrek the Third” (2007) and the R-rated comedy “Bad Teacher” (2011). 

“Years ago, right after she quit seeing Justin Timberlake, I got set up on a date with Cameron Diaz,” Perry wrote in his memoir titled “Friends, Lovers, and the Big Terrible Thing,” released on Tuesday. 

Perry continued: “At the time, I was working out a lot and had developed big arms. For the date I prepared accordingly, taking a long walk with my sleeves rolled to my shoulders so that my guns were appropriately tanned (pro tip: this helps them look even bigger). Yes, I literally tanned my arms for this date.”

Matthew Perry in December 2006.

Matthew Perry in December 2006.

Kevin Winter/Getty Images



Perry said that despite being adequately prepared for his date with Diaz, things didn’t go according to plan when they met in a group setting.

“The date was at a dinner party with a bunch of other people, but upon seeing me, Cameron got almost instantly stoned — it was clear that she wasn’t interested in me at all,” he said.

“But the party went on nevertheless, and at one point we were all playing a game — Pictionary, I think,” Perry continued. “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.

“Or, at least, that’s what she meant to do,” he said. “But she missed and, instead, punched me smack in the side of my face.”

Perry said that he was caught off guard and left stunned by Diaz accidentally punching him. 

“‘Are you fucking 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.

A representative for Diaz didn’t immediately respond to Insider’s request for comment. 

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