Celebrity Jon Cryer, in New Memoir, Reveals He Dated Demi Moore – Before His Costar Ashton Kutcher! "It was awkward in that I'm not sure she even told him that we dated," Cryer told Entertainment Tonight By Jacqueline Andriakos Published on April 7, 2015 08:30 AM Share Tweet Pin Email Photo: Jason LaVeris/FilmMagic; Stefanie Keenan/Getty Jon Cryer has more in common with his Two and a Half Men costar Ashton Kutcher than fans may realize. The actor, 49, revealed in his new memoir So That Happened a piece of his dating history involving Kutcher’s ex-wife Demi Moore, 52. Cryer and the actress dated 30 years ago around the time that they starred together in the 1984 romantic comedy No Small Affair, he revealed in the new tell-all, which hit shelves Tuesday. The most awkward part? They didn’t exactly tell his sitcom buddy upfront. “It was awkward in that I’m not sure she even told him that we dated,” Cryer told Entertainment Tonight in an interview posted Monday. “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,” he remembered. (Kutcher and Moore finalized their divorce in November 2013.) That’s not the only secret Cryer was keeping close to his chest. After his split from his first wife Sarah Trigger in 2004, Cryer hired a prostitute, he admits in his book. “It’s not the proudest moment of my life,” he told ET. He also hoped his 14-year-old son Charlie wouldn’t come across his past on the Internet once the excerpts hit the Web. “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 said in the interview. “So I told him the facts of it, and he said, ‘Yeah, I’m not surprised.’ I was like, ‘Wow, okay!’ ” RELATED VIDEO: Demi Moore s Changing Looks!