Jon Cryer Says He Didn’t Lose His Virginity To Demi Moore, Despite Her Memoir Claiming Otherwise

Demi Moore’s recently published memoir claims that she took Jon Cryer‘s virginity. But as it turns out, this was not the case. The Two and a Half Men star says that although he might have seemed like a virgin at the time, he had actually lost his virginity in high school.

Keep reading to find out more fascinating details about their whirlwind romance. 

Demi Moore
Demi Moore in 2014 | Tommaso Boddi/WireImage

Demi Moore and Jon Cryer both starred in ‘No Small Affair’

Moore and Cryer got to know each other on the set of the 1984 film, No Small Affair. In the movie, Cryer plays a 16-year-old photographer who falls in love with a 22-year-old nightclub singer (played by Moore.)

Similar to their on-screen personas, Cryer became enamored with Moore off-screen as well. And despite their age difference (Cryer was 19 at the time, while Moore was in her mid-20s,) they had a short-lived romance. 

“We were both just starting out, and we were kind of looking for a friend and an ally,” Cryer tells Entertainment Weekly. “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,” he laughs.

Cryer adds, “She thought that she had taken my virginity and she felt bad. It’s funny because I was on Twitter one morning, and then this headline comes up and says, ‘Demi Moore took Jon Cryer’s virginity.’ And I was like ‘Oh my goodness!'”  

Jon Cryer says he didn’t lose his virginity to Demi Moore

Jon Cryer attends the performance of "Love Letters" on July 30, 1991
Jon Cryer attends the performance of “Love Letters” on July 30, 1991 | Ron Galella Collection via Getty Images

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In Moore’s 2019 memoir, she writes how she took the Pretty In Pink star’s virginity.

“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 continued, 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.”

Although Cryer was madly in love with his co-star, he claims that he didn’t lose his virginity to Moore. 

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He told Twitter,

“Well, the good thing about this is she doesn’t have to feel bad about it anymore,” he wrote. “Because while I’m sure she was totally justified making that assumption based on my skill level (and the stunned look on my face at the time), I had actually lost my virginity in high school. But she’s right about the other part. I was over the moon for her during a very troubled time in her life. I have nothing but affection for her and not a regret in the world.”

Jon Cryer was ‘amazed’ that Demi Moore wanted to be with him

Cryer is forever grateful for the love he shared with Moore. And although he might have fallen harder for Moore than vice versa, he still has nothing but love for the star.

In an interview with The Meredith Vieira Show, he said that he was both “terrified” and “amazed” about being with the actress. 

“She was about 24, and I was 19. I was straight out of high school, and I was just terrified of this gorgeous woman,” Cryer laughs. “But it was just one of those whirlwind things, you know. We were both really excited to be in the movie, and she was fresh out of General Hospital.” 

“It was all sort of a blur,” he continues. “Honestly, if you dated Demi Moore, it would kind of be a blur too. I recall being amazed by it on a daily basis.”