Jon Cryer was “over the moon” in love with Demi Moore before she broke his heart - 24/7

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

Jon Cryer became a worldwide star thanks to his work on the television series Two and a Half Men, where he starred alongside Charlie Sheen as Alan Harper.

The actor had his big breakthrough at the age of 21, in the 1986 film Pretty in Pink, but that wasn’t the first time he had stood in front of a Hollywood camera.

In 1984, Cryer starred in the film No Small Affair, alongside Demi Moore; his first big production. The actors reportedly not only became working colleagues, but also engaged in a romantic affair. 

Cryer turned out to be more in love with Demi Moore than she was in love with him, and their romance didn’t last for long. Years later, in her 2019 memoir, Moore revealed that she had taken his virginity. However, Cryer denied this was remotely close to being accurate, and revealed other details about the actress and their relationship.

Here’s all you need to know about Moore and Cryer’s love affair.

Jon Cryer, Demi Moore
Youtube/Tom Simon

Before Jon Cryer turned into a star on the sitcom Two and a Half Men, he had actually already had a long and successful acting career. Plainly put, it wasn’t Two and a Half Men that made him a brilliant and celebrated actor, though the sitcom was undeniably his most prominent role yet.

Jon Cryer – acting career

As it happens, many of his critics doubted that he was destined to reach the upper echelons of on-screen stardom.

On April 16, 1965, Cryer was born in New York City. His parents, mother Gretchen Cryer and father David Cryer, worked as actors. One might say that Jon was born for the stage.

“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 got to hang out backstage at on and off-Broadway theaters, and his father was actually in a production called The Fantasticks, which ran off-Broadway 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.”

At first, Cryer fell in love with the theater. At the same time, however, he loved movies, and from the age of seven, he recalled watching pretty much every television show going.

Jon Cryer
Shutterstock/s_bukley

When Jon was four years of age, his parents divorced, and his mother assumed custody of Jon. She worked as both an actress and writer, and made sure that her son joined her at work. That led to his first job in acting, as he appeared alongside his mother in a television commercial for vitamins.

“It was this or nothing”

Jon was hooked, and decided to pursue a career in the entertainment business. He got his first job as an usher – the person who usually welcomes and shows people where to sit – and later as a house manager, a position that involved him cleaning toilets.

It should go without saying that the entertainment industry, especially in New York, is very competitive. As a result, Cryer learned early on that acting wasn’t necessarily something one could make a living out of. But still, the up-and-coming actor, passionate about the art of performing in front of the camera, didn’t care about the 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.”

Jon Cryer, Demi Moore
Youtube/Tom Simon

Instead of going to college, Cryer put everything he had into one basket: to try and make it as an actor. He went to study at the Royal Academy of Dramatic Arts in London, appeared in some productions, and made guest appearances on television.

Jon Cryer and Demi Moore – romance

In 1984, Cryer starred in the film No Small Affair. It was his first-ever production, and he got a leading role alongside then-up-and-coming actress 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 sure was a solid start to Cryer’s Hollywood career. But the film No Small Affair wouldn’t go down in history as his most significant role. Rather, these days, the film’s probably more famous for its actors, Cryer and Moore, and the romance they engaged in.

Demi and Jon starred as Laura and Charles in No Small Affair. The plot centers around Charles, who gets into an affair with the glamorous singer Laura, who at 23 is much older than him in the film. But, as mentioned, the romance between Cryer and Moore wasn’t just confined to the screen.

In her memoir Inside Out, released in 2019, Demi Moore revealed that she and Jon Cryer had a sexual relationship during filming. Moreover, Moore claimed that she took Jon Cryer’s virginity.

Now, according to the Two and a Half Men star, that wasn’t entirely true. It didn’t take long for Cryer to respond via Twitter, denying that Moore had taken his virginity.

Demi Moore
Shutterstock/DFree

“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

In another tweet, he added: “But she’s right 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.”

Demi and Jon had something more than just a sexual relationship. At least, that was what Jon thought. Speaking on The Meredith Viera Show, he spilled the truth about his time with Moore, saying that he was way more invested in their relationship than she was.

Eventually, it was a heartbreaking incident that made him realize he was alone in their romance.

“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.”

Demi Moore
Shutterstock/DFree

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.”

Even though Cryer was left heartbroken by Moore, theirs wasn’t the last of his relationships.

In 1999, he married his first wife, Sarah Trigger. They welcomed son Charlie Austin Cryer in 2000, though the couple then divorced in 2004.

At that point, Cryer was lost. The divorce broke his heart, and he felt “undatable.” In his memoir (as per the Hollywood Reporter), he revealed that he even went as far as paying for sex.

“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.

Jon Cryer, Lisa Joyner
Shutterstock/Kathy Hutchins

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.”

After the big success with Two and a Half Men, Cryer met and wed his second wife, television host, actress, and producer Lisa Joyner.

It’s safe to say that the couple’s first meeting wasn’t the traditional love story. It took Cryer six weeks to make his first move, and by that point, Lisa had already formed a pretty clear picture regarding what she thought her and Cryer’s relationship was going look like.

“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!’”

Jon Cryer, Lisa Joyner
Shutterstock/Kathy Hutchins

“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.”

Philanthropy work

“‘Sorry, I said. Just nervous’.”

The two got engaged and, in 2007, tied the knot at the Chapel at Pueblo Bonito Sunset Beach in Cabo San Lucas, Mexico. They went on to adopt daughter Daisy Cryer in 2009.

Together, Jon and Lisa are working with the California organization Hope of the Valley to curb homelessness in the area. They even donated $30,000 to the organization. Moreover, the couple is leading a fundraising marathon and hopes to build tiny home communities for homeless people.

Cryer – who continued his acting career after Two and a Half Men, starring in NCIS for a short while, among other jobs – has also been very active in the community concerning children with disabilities.

Jon Cryer and Demi Moore might not have been meant for each other, but the Two and a Half Men actor sure found true love later in life. We wish him and Lisa Joyner all the best.

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