Demi Moore was still married to Ashton Kutcher when he joined Jon Cryer on “Two and a Half Men” in 2011, and Cryer revealed that he couldn’t stop thinking about his own past with Moore while trying to get to know his new costar. “It was a little bit awkward because she and I had dated when he was 7, so there was that aspect,” he quipped on “Live with Kelly and Michael.” Cryer recalled that he was maybe laughing a bit too hard at Kutcher’s jokes while he continued to wonder whether Kutcher knew that he had dated Moore. After watching him squirm for a bit, Cryer recalled Kutcher telling him, “She told me. It’s cool. Don’t worry about it.”
Two months after Kutcher appeared in the season premiere of the retooled sitcom, he and Moore announced their separation. “Two and a Half Men” ended in 2015, but four years later, both Kutcher and Cryer would find themselves starring together in Moore’s 2019 memoir.
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In “Inside Out,” Moore recounted how Cryer fell head-over-heels for her after they appeared together in the 1984 movie “No Small Affair.” She claimed that she took his virginity and would later regret the way their short-lived romance played out. “It pains me to think of how callous I was with his feelings — that I stole what could have been such an important and beautiful moment from him,” she wrote (via Page Six).
