Jon Cryer Reveals in Memoir That He Dated Demi Moore Long Before Ashton Kutcher, Admits to Hiring Prostitutes

Jon Cryer and Demi Moore
Jon Cryer revealed in his new memoir So That Happened that he dated Demi Moore long before his Two and a Half Men costar Ashton Kutcher married the actress; plus, he recently told his teen son about hiring a prostitute. David Livingston/Getty Images; JB Lacroix/WireImage


It turns out that Jon Cryer shares a bond with his former costar Ashton Kutcher that goes beyond Two and a Half Men. Cryer revealed in his new memoir, So That Happened, that he dated Demi Moore many years before Kutcher began seeing her.

More than three decades ago, the Pretty in Pink actor, 49, and fellow brat packer Moore, 52, starred in the 1984 flick No Small Affair. While their relationship fizzled out, Cryer revealed just how small of a world Hollywood is when Kutcher came into the studio for chemistry screenings after Charlie Sheen‘s sudden departure from the CBS sitcom in 2010. Kutcher, 37, officially joined the cast in May 2011.

jon cryer and demi
Demi Moore and Jon Cryer in “No Small Affair”, 1984 Columbia Pictures/courtesy Everett Collection

“It was awkward,” Cryer told Entertainment Tonight on Monday, April 6. “I’m not sure she even told him that we dated. In our first meeting, we’re trying to have that let’s-create-that-chemistry meeting and the whole time I’m looking at him, waiting for him to drop the bomb.”

At the time, Kutcher was married to Moore. In November 2011, the actress announced their split after six years of marriage, and the couple finalized their divorce in November 2013.

demi and ashton
Demi Moore and Ashton Kutcher in 2010 Florian Seefried/GC/Getty Images

Cryer also experienced firsthand a painful divorce back in 2004 from Sarah Trigger. In his memoir, which was recently excerpted by The Hollywood Reporter, Cryer admitted to hiring a prostitute after their split.

“My forays into prostitution were about as awkward as you might imagine,” Cryer wrote in his book. “I went with an out-call for my first try, which means they come over to your house. My chosen vendor drove a white BMW and sported a sexy Finnish accent. It was really a very friendly experience, maybe because the act of having sex is quite the conversational icebreaker. The next time, I went to her place, which probably wasn’t really her place. We sat down, tried to make small talk and halfheartedly stumbled into a conversation about recent fluctuations in the stock market. Somehow I ended up spending 25 minutes of my hour helping her with financial planning.”

According to the actor, Cryer had to discuss that salacious detail with his teenage son Charlie, 14. “I went through a divorce, you know,” Cryer told ET. “It’s not the proudest moment of my life.”

The actor recalled how he warned his son about the incident. “I found myself picking my son up at school and having to give him a heads up that, ‘Oh, you might read something on the Internet today that’s a little curious,'” Cryer recalled. “So I told him the facts of it, and he said, ‘Yeah, I’m not surprised.’ I was like, ‘Wow, okay!'”

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