Jon Cryer was “over the moon” in love with Demi Moore, but she broke his heart

In the television series Two and a Half Men, where he co-starred with Charlie Sheen as Alan Harper, Jon Cryer rose to fame on a global scale.

The actor had previously appeared in front of a Hollywood camera before his big break came at the age of 21 in the 1986 movie Pretty in Pink.

His first major motion picture, No Little Affair, starring Cryer and Demi Moore, was released in 1984. According to reports, the performers not only became coworkers but also got involved in a relationship.

Cryer and Demi Moore’s romance didn’t survive very long since it turned out that he was more in love with her than she was with him. Years later, Moore admitted that she had stolen his virginity in her 2019 autobiography. Nevertheless, Cryer refuted this and disclosed additional information regarding the actress and their relationship.

This is all the information you need to know about Moore and Cryer’s romance.

Jon Cryer actually had a long and successful acting career before he became a star on the sitcom Two and a Half Men. Simply said, despite the fact that the sitcom was without a doubt his most notable part to date, Two and a Half Men did not make him a wonderful and renowned actor.

Acting career of Jon Cryer

In actuality, many of his detractors questioned whether he was destined to rise to the pinnacles of on-screen celebrity.

Cryer was born in New York City on April 16, 1965. Gretchen Cryer, his mother, and David Cryer, his father, were both actors. It may be said that Jon was destined for the theater.

“I knew pretty much, from when I was eight or nine years old, that this is what I wanted to do, just because it’s so stupid, it’s such a silly job,” he explained.

“I kind of can’t believe people get paid for it.”

Cryer had the opportunity to hang around backstage at both on- and off-Broadway theaters, and his father had a part in The Fantasticks, an off-Broadway show that ran for more than 30 years.

“When you’re a little kid, and you’re backstage seeing all these crazy, magical people floating in and out of your life, it can’t help but cast a spell on you,” he said.

“I wanted to be a part of that.”

Cryer at first developed a deep affection for the theater. But he also enjoyed watching movies, and starting at age seven, he recalls watching just about every television program on the air.

When Jon’s parents got divorced when he was four years old, his mother took care of him. She pursued careers as a writer and actor while making sure her son was there at work. That resulted in him landing his first acting role, where he shared the screen with his mother in a vitamin ad.

Jon became obsessed and made the decision to work in the entertainment industry. His first job was as an usher, the person who welcomes and directs guests to their seats. Later, he worked as a house manager, which required him to clean restrooms.

It should go without saying that the entertainment business is extremely competitive, particularly in New York. As a result, Cryer discovered early on that acting wasn’t always a viable career option. The aspiring actor, however, was more interested in the art of performing in front of the camera than he was in making money.

“It was one of those things where I never gave myself another option. I never really had anything to fall back on. It was this or nothing. But I didn’t give myself an alternative,” Cryer said.

“And I also got incredibly lucky because when I was about 17 or 18, there was a huge burst of teen movies and lots of parts for people my age. You can’t bank on that,” he added.

“But I just got lucky. So I started working when I was 18 got my first couple of jobs. My first gig was as Matthew Broderick’s understudy in Brighton Beach Memoirs; I lasted six weeks before they fired me.”

Cryer decided against attending college and invested everything he had into being a successful actor. He traveled to London to further his studies at the Royal Academy of Dramatic Arts, had cameos in a few plays, and appeared on television.

Demi Moore and Jon Cryer have a romance.

Cryer featured in the movie No Little Affair in 1984. That was his first ever production, and he was cast as the lead opposite rising star Demi Moore.

In their film review, The New York Times wrote: “Jon Cryer, who plays Charles, makes him a toothy, good-humored adolescent with style.”

It was undoubtedly a strong beginning for Cryer’s Hollywood career. But his most memorable performance would not be in the movie No Little Affair. Nowadays, the movie is arguably more well-known for its stars, Cryer and Moore, and their romance.

In No Little Affair, Demi and Jon played Laura and Charles, respectively. The story revolves around Charles, who has a relationship with the glitzy singer Laura, who is significantly older than Charles in the movie at 23. Yet, as already indicated, Cryer and Moore’s relationship went beyond the confines of the silver screen.

In her 2019 autobiography Inside Out, Demi Moore made it known that she and Jon Cryer had a sexual relationship while filming the movie. Moore also allegedly stole Jon Cryer’s virginity.

Now, the Two and a Half Men actor claimed it wasn’t totally accurate. It didn’t take Cryer long to comment on Twitter and refute Moore’s claim that he had stolen his virginity.

“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 skill level (and the stunned look on my face at the time), I had actually lost my virginity in high school,” Cryer wrote on Twitter.

Demi Moore broke Jon Cryer’s heart
But she’s accurate about the other half, I was ecstatic for her during a really trying moment in her life, he continued in another tweet. I love her unconditionally and have no regrets in the world.

More than just a sexual connection existed between Demi and Jon. Jon, at least, believed that. He revealed the truth about his connection with Moore during an appearance on The Meredith Viera Show, claiming that he put a lot more effort into it than she did.

He eventually realized he was the only one in their romance after a terrible event.
“I went to her house, and her housekeeper greeted me,” Cryer recalled. “And I asked, ‘Oh, where’s Demi?’ She said, ‘She’s out with her boyfriend.’ And I said, ‘But I’m her boyfriend.’”

Though it was unfortunate at the time, Cryer hasn’t held any grudges against Moore. Instead, he added that he thought she was “The One.”

“That probably happened two days into the relationship,” Cryer said. “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.”

Jon Cryer – marriages, divorce, wife, children
In her memoir, Moore also described her relationship with Cryer, admitting that she hadn’t treated him the right way. She expressed regret for being “callous” with his feelings at the time, declaring “that I stole what could have been such an important and beautiful moment from him.”

Although Moore broke Cryer’s heart, their relationship wasn’t his final one.

He wed Sarah Trigger, his first spouse, in 1999. Charlie Austin Cryer was born to them in 2000, although the couple later got divorced in 2004.

Cryer was disoriented at that point. His heart was broken by the divorce, and he felt “undatable.” He admitted in his memoir that he even paid for sex, according to the Hollywood Reporter.

“I was in a bad state right after my divorce, and I certainly didn’t feel dateable. I was an emotional basket case. What good was I to any woman I might have interest in? I decided I might as well pay someone for company and certain intimate pleasures so that I could at least get my equilibrium back with the opposite sex,” Cryer wrote.

Charlie Sheen – his co-star on Two and a Half Men – suggested a “few online purveyors”. Cryer decided to go for it, writing that his first experience was “as awkward as you might imagine.”

Wife Lisa Joyner
“It was really a very friendly experience, maybe because the act of having sex is quite the conversational icebreaker. The next time, I went to her place, which probably wasn’t really her place,” Cryer wrote.

“We sat down, tried to make small talk, and halfheartedly stumbled into a conversation about recent fluctuations in the stock market. Somehow I ended up spending 25 minutes of my hour helping her with financial planning.”

With the popularity of Two and a Half Men, Cryer met Lisa Joyner, a television personality, actor, and producer, and they got married.

It’s reasonable to assume that the beginning of the couple’s relationship wasn’t the typical love story. Six weeks passed before Cryer made his first move, and by then Lisa had a pretty good idea of what she imagined her and Cryer’s relationship would entail.

“I thought he was going to be my new best gay friend,” Lisa recalled.

“We got to know each other. And had it not happened that way, I don’t think we’d be together. But, when we did kiss…I was done, I really was done. I said, ‘Oh, okay!’”

“She ventured cautiously:” At first I wasn’t sure if you were gay or not,’” Cryer wrote in his memoir, So That Happened.

“She looked down, then continued Y’know, because we’ve been going on dates for six weeks, and you’ve never even kissed me good night. Sorry, I said. Just nervous’.”

In 2007, the couple wed at the Chapel at Pueblo Bonito Sunset Beach in Cabo San Lucas, Mexico, after becoming engaged. In 2009, they adopted Daisy Cryer, a daughter.

Jon and Lisa are collaborating with the Californian charity Hope of the Valley to reduce local homelessness. They even gave the charity $30,000 in donations. The pair is also organizing a fundraising marathon with the goal of creating tiny home communities for the destitute.

After Two and a Half Men, Cryer maintained his acting career and briefly starred in NCIS, among other roles. He has also been a highly active member of the community when it comes to children with disabilities.

Even though Demi Moore and Jon Cryer were not destined to be together, the Two and a Half Men actor did find true love in his latter years. He and Lisa Joyner have our warmest wishes.

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