Matthew Perry
Credit: Charley Gallay/Getty Images for Lili Claire

Friends star Matthew Perry has recalled being on a group date with Cameron Diaz shortly after her split with Justin Timberlake in his newly-released memoir, Friends, Lovers, and the Big Terrible Thing. It was sometime after 2007 when the couple were set up but according to the actor, their first date didn’t exactly go very well.

While at a group dinner party, the book alleges that Diaz had gotten “immediately stoned” and “wasn’t interested at all” in the sit-com star. Perry, now 53, writes that he said “something witty” during a game of Pictionary (classic) and instead of hitting his shoulder, the Charlie’s Angels actress put her on-screen skills to good use when she “accidentally” missed and punched his face instead. “Are you f***ing kidding me?” he remembers replying.

Cameron Diaz
Credit: James Devaney/WireImage

Diaz had been dating Timberlake between the years 2003 and 2007 before a very public split.

Within Perry’s new book we also received insight into his brief relationship with Julia Roberts in the ’90s. After trying to “woo” the actress into appearing as a special guest on Friends, the pair eventually fell into a relationship. At the time Perry was struggling with drug addiction. He wrote that “dating Julia Roberts had been too much” and that his mental health and self-esteem issues led to them breaking up.

Matthew Perry Julia Roberts
Actor Matthew Perry and actress Julia Roberts hug each other on the set of “Friends. Credit: Liaison/Getty Images

“I had been constantly certain that she was going to break up with me,” Perry wrote. “Why would she not? I was not enough; I could never be enough; I was broken, bent, unlovable. So instead of facing the inevitable agony of losing her, I broke up with the beautiful and brilliant Julia Roberts.”

Perry is currently 18 months sober.