Thanks to his work on the television show Two and a Half Men, in which he co-starred with Charlie Sheen as Alan Harper, Jon Cryer rose to international fame.

At the age of 21, the actor made his major breakthrough in the movie Pretty in Pink, but it wasn’t his first experience in front of a Hollywood camera.His first significant role was in the 1984 movie No Small Affair with Demi Moore.

According to reports, the actors not only started working together but also started dating.

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.

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.

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.

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.

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.”

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.

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

In No Small 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. However, 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.

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

Moore also discussed her relationship with Cryer in her memoir, acknowledging that she hadn’t treated him fairly. She expressed remorse for being “callous” with his emotions at the time, saying “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.”

“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.”

Following 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.

To lessen local homelessness, Jon and Lisa are working with the Californian nonprofit Hope of the Valley. They even donated $30,000 to the organization. In order to build small home communities for the poor, the pair is also planning a fundraising marathon.

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.