When Matthew Perry went on a date with Cameron Diaz, he had everything planned out. In his memoir, he wrote that he orchestrated several details through the night to ensure that Diaz focused on his best asset — his arms — which had grown due to working out and eating healthier. Perry started with the basics: He chose to wear a long-sleeved shirt that he could roll up during the long walk he planned.
To really make his arms pop, he even got a fake tan done especially for the date. Perry detailed how it all went down, recalling, “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.” Nonetheless, Perry tried to have some fun at the party by joining a game of Pictionary, but things took a turn for the worse when Perry decided to make good use of his sense of humor.
He 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 blow didn’t hit its target, and she instead ended up punching Perry in the face. At the time, Perry was too stunned to do anything except say, “Are you f***** kidding me?” but in hindsight, he marveled at the irony of getting punched while trying to make a big deal out of his arms.