Jon Cryer 'Couldn't Have Been Happier' to Meet Demi Moore — Inside Their Romance

Demi Moore and "Two and a Half Men" actor Jon Cryer's romance was born after the pair starred together in the 1984 film "No Small Affair." Cryer was thrilled to be cast alongside Moore, and soon after, an affair bloomed.

Moore played the young nightclub singer, while Cryer's role was that of a nineteen-year-old photographer who fell in love with Moore's character. However, the romantic feelings spilled into real life, and Moore would detail in her book "Inside Out" that Cryer was head over heels for her.

She also disclosed that Cryer had lost his virginity to her, a claim that the "Hot Shots!" actor vehemently denied. Cryer shared that he had been fresh in the industry while Moore had already worked on "General Hospital" and "Blame It On Rio."

When he was cast for the role in "No Small Affair," he was surprised that the casting team kept him, and he couldn't have been happier upon discovering that Moore would be his costar.

Cryer described Moore as being fun, engaging, and stylish. He also thought she had an approachable air about her. They hit it off after their first screen test.

Moore had a few more years of experience than him in the industry, while in contrast, Cryer was "innocent" in the Hollywood nightlife. However, when Moore offered to show Cryer around, he was thrilled.

Moore would take Cryer to dinners and parties, introducing him to her crowd. He also shared that Moore had a great attitude about her experiences and even dragged him to the "General Hospital" set.

According to People, Cryer confessed in his 2015 memoir "So That Happened" that Moore was his "inaugural Hollywood romance." When she first kissed him during one of their many nights out, he "fell" hard for her.

CRYER DENIED MOORE'S REVELATIONS

Despite their roller-coaster affair, the romance was short-lived, as Moore would later admit that she had not been in the best place to take care of someone else's feelings. She apologized for having "taken his virginity," then being callous with his feelings and stealing "what could have been such an important and beautiful moment from him."

In response to her admissions, Cryer brushed off the claims saying that while he had been head over heels for her, he had already lost his virginity in high school. He, however, told Moore that she had no reason to continue feeling bad about their past dalliance. He shared according to CNN:

"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."

But while he had no regrets about their romance, Cryer faced awkward situations after being cast on "Two and A Half Men" alongside Ashton Kutcher, who dated and married Moore long after her romance with Cryer failed.

Cryer recalls that before Kutcher, who replaced Charlie Sheen on the sitcom, arrived for the chemistry meeting, he had been a nervous wreck wondering if Moore had told him about their romance.

Another worrying aspect of their romance was that Moore's future husband, Kutcher was only seven years old when Moore and Cryer dated. In addition to the awkward situation, Moore had also dated Sheen's brother Emilio Esteves, but they never made it to the alter despite being engaged.

Despite their breakup, the two still talked, and Cryer recalls Moore once coming to a restaurant where he was hanging out with friends to say hello to him. Despite the relationship not working out, Cryer was happy to see Moore newly sober and making the most of her career.

ANOTHER FAILED ROMANCE

Moore is known for her numerous roles in film, as much as she is for her many failed relationships. After her romance with Cryer ended, Moore met Esteves on the 1985 film "St. Elmo's Fire" set, and the two hit it off.

However, despite the obvious attraction, they only pursued their relationship further after Moore beat her drinking habits. Six months after she became sober, the couple got engaged and began planning their December 1986 wedding.

However, that was not to be because just after sending out their wedding invites, a friend told Moore that they had spotted her fiancé with another woman, and when Moore confronted Esteves on the same, he denied it.

Moore also claimed that Esteves had been cheating on her with an ex-girlfriend, and despite initially denying it, he would later admit to the affair after finding out that the ex-girlfriend had fallen pregnant. The two soon broke off the engagement but remained friends.

In 2003, Moore started dating actor Ashton Kutcher who is 16 years her junior. The two married in 2005, with the issue of their ages hitting the headlines for a long time. Age notwithstanding, Moore says they were in sync and did not feel their age difference.

However, the couple could not make their marriage work after rumors became rife that Kutcher was unfaithful to Moore on their wedding anniversary. In 2011, the "A Few Good Men" actress announced that they were separating, with their divorce becoming final in 2013.

In 1987, Moore started seeing actor Bruce Willis. The duo married the same year and welcomed three daughters, Rumer, Scout, and Tallulah. They, however, split in 2000.

Moore is, however, not one to deny love another chance. People confirmed that the actress has been dating Swiss chef and acclaimed New York City restaurateur Daniel Humm. The two were first spotted together in March 2022 at the front row of Chloé's Fall/Winter 2022 runway show for Paris Fashion Week.

Moore's new man owns Eleven Madison Park, a Manhattan eatery, and opened the NoMad restaurants in Los Angeles and New York and Davies and Brook in London. He is also the author of several cookbooks.

CRYER IS NOT PROUD OF HIS DIVORCE

After his breakup with Moore, Cryer found and fell in love with Sarah Trigger. The two married in 1999 and had a son, Charlie Austin. Theirs was a troubled marriage, and after only five years, they went their separate ways.

They divorced in 2004, and the actor hired a callgirl, something he says he is not proud of. He said: "I went through a divorce. It's not the proudest moment of my life."

The duo underwent a nasty divorce, and later, Trigger dragged Cryer to court looking to increase the child support from the initial $8,000 to $88,000, a request that the judge shut down immediately.

After his divorce, Cryer once again found love in 2007 after meeting Lisa Joyner. The two tied the knot in Mexico and later adopted a baby girl named Daisy, born on August 11, 2019.