When did Demi Moore and Jon Cryer date? 'Two and a Half Men' star reveals he was unaware of star's addiction issues during their relationship

Jon Cryer opened up about dating
Jon Cryer opened up about dating 'Brat Pack' member Demi Moore (Image via Instagram/@demimoore, @mrjoncryer, @andrewtmccarthy)

Two and a Half Men star Jon Cryer opened up about his time dating Striptease actress Demi Moore. In an interview with People magazine published on Saturday, June 7, 2024, Cryer recalled the time that he and Moore were involved romantically while working on the 1984 film No Small Affair. The actor revealed that he was not aware of Moore's struggle with drugs at the time. He told the publication:

"She was already struggling with a drug problem. One that I was blissfully unaware of until a couple of weeks before the movie ended."

Moore had entered rehab during the same decade due to her issues with alcohol and drugs. Demi Moore was last involved in a romantic relationship with Swiss chef Daniel Humm, before calling off the relationship in late 2022. Jon Cryer, on the other hand, has been married to reporter Lisa Joyner since 2007.

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"I guess our particular affair was, in fact, pretty small"— Jon Cryer on his relationship with Demi Moore

In an interview with People magazine, Two and a Half Men's Jon Cryer recalled his brief relationship with Demi Moore in the 80's. As mentioned above, the actor remembered being "blissfully unaware" of Moore's drug issues until the end of filming for their 1984 flick No Small Affair. He told the publication:

"We dated for a short time while we were working on No Small Affair, but I guess our particular affair was, in fact, pretty small."

However, the actor was still deeply smitten with Moore at the time. He stated:

"What would always be great about her was already evident; that incredible combination of vulnerability, toughness and beauty."

Cryer also called Moore "incredibly charismatic" and conceded that the Indecent Proposal star had a better grasp of the movie industry than he did. The actor said that Moore "knew everybody in town" but both of them were still quite nervous while shooting No Small Affair as this was their first time being cast as leads.

In her 2019 memoir Inside Out, Moore claimed that she believed she was the first person that Jon Cryer entered into a s*xual relationship with. However, Cryer took to X in the same year to state that while Demi was fair to make that assumption, however, he actually lost his virginity in high school. The actor further tweeted:

"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."

Demi Moore went on to film, the American coming-of-age cult classic St. Elmo's Fire the year after No Small Affair. The late Joel Schumacher's film was not well received at the time of its release but over time, it has earned itself a cult classic status. More importantly, Demi Moore entered rehab right after the movie was released.

As per a 1997 People magazine interview, director Joel Schumacher, who himself experienced issues with substance abuse told the actress that he was "firing her" if she didn't get clean. He told the publication at the time:

"I didn’t want to do what they had done with John Belushi, which was just give her the money to kill herself."

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John Belushi was a prominent actor, musician, and comedian who tragically passed away in 1982 aged only 33 due to a combined drug intoxication from both heroin and cocaine. Belushi had struggled with addiction throughout his life. Schumacher further added in the interview:

"When she came out, we hired a counselor to live with Demi during filming."

At the time, Schumacher stated that Demi had been sober "ever since." However, as per People, the actress did relapse a few years later in 2012 and had to enter rehab once again for her addiction problems as well as an eating disorder.


Jon Cryer is all set to make an appearance in Andrew McCarthy's upcoming Hulu documentary BRATS, which will chronicle the lives of the elusive "Brat Pack," a group of talented young stars who appeared in multiple coming-of-age films of the 80s. Demi Moore, a core member of the "Brat Pack" will also feature in the documentary, which will premiere on Hulu on Thursday, June 13, 2024.

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