The year was 2007, and Cameron Diaz had just broken up with Justin Timberlake when her friends thought it was time for her to meet someone new. The person they had in mind was funnyman and fellow actor Matthew Perry. So, they organized a get-together so the two could become better acquainted. Unfortunately, things did not go well. As the “Friends” star recalled in an excerpt published by Business Insider, he was looking his best — “I was working out a lot and had developed big arms” — and even worked on his tan ahead of the meetup, but it was all for nothing. “The date was at a dinner party with a bunch of other people, but upon seeing me, Cameron got almost instantly stoned,” he wrote. “It was clear that she wasn’t interested in me at all.”
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Even so, neither he nor Diaz left. The party went on, and they eventually found themselves playing Pictionary. That’s when things went from bad to worse. “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.” Except she missed, and as Perry recalled, she missed. Instead, Diaz smacked him in the face. While it was an accident, Perry’s response perfectly encapsulated their night: “Are you f**king kidding me?” he seethed. Needless to say, Perry and the “Charlie’s Angel” star were not meant to be.
