Jon Cryer Learned Demi Moore Was Dating Someone Else While They Were in a Relationship: ‘I Got in a Lot Deeper Than She Did’

Back in the 1980s, Jon Cryer was madly in love with Demi Moore. And for a short period, the actors shared a whirlwind romance. Yet sadly, the Ghost actor admits that she didn’t take the relationship as seriously as Cryer. And during a heartbreaking incident, the Two and a Half Men actor learned that Moore was dating other people while they were supposedly boyfriend and girlfriend. 

Studio portrait of actor John Cryer, 1986
Studio portrait of actor John Cryer, 1986 | Lynn Goldsmith/Getty Images

How did Demi Moore and Jon Cryer meet?

Moore and Cryer met on the set of No Small Affair, a movie which stars both of the actors. The 1984 film centers around a 16-year-old photographer (Cryer) who falls madly in love with a 22-year-old nightclub singer (Moore.) 

And as it turns out, this dynamic occurred off-screen as well. Cryer quickly fell for Moore, and he fell hard. He reveals in an interview with Entertainment Weekly, “We were both just starting out, and we were kind of looking for a friend and an ally. You know, we kind of fell for each other. Or at least, I fell for her. She sort of revealed in her book that it was a little less important to her than it was to me.”

In her recently published memoir, Moore suggests that she mistreated Cryer during their relationship. She even claims that she took the Pretty in Pink actor’s virginity, which isn’t the case, as Cryer points out. (He actually lost his virginity in high school, prior to meeting Moore.)

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“It pains me to think of how callous I was with his feelings,” she writes of Cryer. “That I stole what could have been such an important and beautiful moment from him.”

Moore continues, saying, “I was sort of losing it right then, and I was definitely not in a place to take care of someone else’s feelings.”

Jon Cryer says Demi Moore was dating other people while they were in a relationship

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Cryer lets his fans in on the heartbreaking incident when he learned Moore wasn’t nearly as invested in their relationship as he was. In a 2015 interview with The Meredith Vieira Show, he spills all the details. 

“I went to her house, and her housekeeper greeted me,” says Cryer. “And I asked, ‘Oh, where’s Demi?’ And she said, ‘She’s out with her boyfriend.’ And I said, ‘But I’m her boyfriend.'”   

Jon Cryer thought Demi Moore was ‘the one’

Still, despite that rather unfortunate moment, Cryer has nothing but love for Moore. He says in the interview that he even thought she was “the one.” “That probably happened two days into the relationship,” he laughs. “I was like, ‘Yes. This is it, I know it. But at the time, she was more grown-up than me and more sophisticated. And I have a feeling I got in a lot deeper than she did.”

And after Moore’s memoir was released, Cryer took to Twitter to praise his ex-lover. 

“I was over the moon for her,” he professed. “I have nothing but affection for her and not a regret in the world.”