It’s not uncommon for co-stars to fall in love while filming a movie. According to Cosmopolitan, many on-screen relationships have transferred to off-screen romances. Some of Hollywood’s It couples actually met and fell in love on sets, such as Blake Lively and Ryan Reynolds. Back in the 1980s, Demi Moore and Jon Cryer also found themselves in a budding romance that bloomed while on set. The duo co-starred in Jerry Schatzberg’s film “No Small Affair” in 1984.
Cryer played Charles Cummings alongside Moore, who played Laura Victor. The film follows a 16-year-old photographer (Cryer) who falls deeply in love with a 22-year-old nightclub singer (Moore) after accidentally snapping a photo of her. Like their characters in the film, the duo quickly fell into a short-lived whirlwind romance. Cryer’s breakout role came two years later when he starred as “John Hughes” in the film “Pretty in Pink.”
According to People, one of Cryer’s most recognizable roles is his portrayal of “Alan Harper” in CBS’s primetime Emmy-winning television series, “Two and a Half Men.” In 2011, Cryer received a star on the Hollywood Walk of Fame for his dazzling performances throughout his career.

Although his relationship with Moore ended decades ago, it has left lasting impressions on both of them. In 2019, Moore released her memoir “Inside Out” where she revealed details about their fling and admitted to being careless with Cryer’s emotions. Yet, despite how things ended, Cryer still cherishes Moore and their time together.

Here’s an inside look into Demi Moore’s and Jon Cryer’s romance.

Demi Moore (ca. 1990), (Paramount Pictures/Getty Images)

Jon Cryer fell fast and hard for Demi Moore, he revealed to Entertainment Weekly. He shared how the former couple was drawn to each other due to their status as actors on the rise.

“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,” he said. “She sort of revealed in her book that it was a little less important to her than it was to me.”

In an interview with The Meredith Vieira Show, the “Pretty in Pink” actor revealed a crucial moment in his relationship with Moore that led him to believe he was more invested than her.

“I went to her house, and her housekeeper greeted me,” recalled 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.’”

Despite the unfortunate discovery, Cryer still has nothing but love for Moore. Later in the interview, the Emmy-winning actor remembered thinking that Moore could be “the one” and joked about falling in love too fast.

“That probably happened two days into the relationship,” he admitted. “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.”

In 2019, Moore released a memoir, Inside Out, which gave readers an inside look into her life of fame and numerous Hollywood romances. Moore also offers a glimpse of her relationship with Cryer and admits that she mistreated his feelings.

“Jon fell for me in real life, too, and lost his virginity to me while we were making that movie.” She wrote.

Jon Cryer (2012), (Vera Anderson/WireImage/Getty Images)

Moore described in her memoir how she felt like she “stole what could have been such an important and beautiful moment from him,” because of her carelessness.

The “Blame it on Rio” actress revealed that during her relationship with Cryer, she believed she took his virginity. A claim that Cryer has since denied. The “Two and A Half Men” actor explained the situation in a series of tweets.

“Well, the good thing about this is she doesn’t have to feel bad about it anymore, because while I’m sure she was totally justified making that assumption based on my my [sic] skill level (and the stunned look on my face at the time), I had actually lost my virginity in high school,” Cryer tweeted.

Although the details of their romantic life are still unclear, Cryer admitted that Moore was right about his feelings for her.

“But she’s right the other part,” he added. “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.”

Since their short-lived romance, Moore went on to have several high-profile romances. The award-winning actress has been married three times. Her first marriage was to Freddy Moore. The “Ghost” actress went on to marry actors Bruce Willis and Ashton Kutcher. She has three children with Willis. Cryer also went on to experience many other loves. In 1999, he married his first wife, British actress Sarah Trigger. They divorced in 2004 and have one son. Cryer married his second wife, Lisa Joyner, in 2007. According to Today, the couple welcomed their first child, a girl named Daisy, whom they adopted in 2009.

Jon Cryer, Charlie Sheen (2009), (Chris Polk/FilmMagic/Getty Images)

Did you know about Demi Moor and Jon Cryer’s past relationship? Have you ever been in a relationship where you were more invested than your partner? Let us know, and be sure to send this to your friends and family.

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