Ashton Kutcher's Former Co-Star Jon Cryer Had A Romance With Demi Moore Too

In an alternate universe, "Two and a Half Men" star Charlie Sheen could have played Demi Moore's husband in the 1993 movie "Indecent Proposal." But while Moore had once been engaged to Sheen's brother, Emilio Estevez, this potentially awkward connection apparently had nothing to do with why Sheen turned the role down. On "The Kyle & Jackie O Show" (via news.com.au), he explained that he simply didn't like the film's ending.

Moore and Estevez were one of the Brat Pack's biggest "It" couples in the '80s, but in her book "Inside Out" (via Vulture), Moore reveals that she split from her "St. Elmo's Fire" costar because she suspected him of being unfaithful. After their breakup, Moore attended the premiere of Estevez's 1987 movie "Stakeout," which is where she met future husband Bruce Willis.

Moore would work with Estevez again when he directed and costarred with her in the 2006 movie "Bobby." By then, there was a new man in Moore's life: Ashton Kutcher, who appeared alongside Moore and her ex in the drama. Perhaps this factoid should have made another of Moore's exes, Jon Cryer, a little less apprehensive about working with Kutcher after he replaced Sheen on "Two and a Half Men." On "Watch What Happens Live," Cryer revealed that meeting Kutcher for the first time was nerve-racking because he had no idea if Kutcher was aware of his romantic history with Moore — which Cryer would later make an embarrassing admission about.

Demi Moore was still married to Ashton Kutcher when he joined Jon Cryer on "Two and a Half Men" in 2011, and Cryer revealed that he couldn't stop thinking about his own past with Moore while trying to get to know his new costar. "It was a little bit awkward because she and I had dated when he was 7, so there was that aspect," he quipped on "Live with Kelly and Michael." Cryer recalled that he was maybe laughing a bit too hard at Kutcher's jokes while he continued to wonder whether Kutcher knew that he had dated Moore. After watching him squirm for a bit, Cryer recalled Kutcher telling him, "She told me. It's cool. Don't worry about it."

Two months after Kutcher appeared in the season premiere of the retooled sitcom, he and Moore announced their separation. "Two and a Half Men" ended in 2015, but four years later, both Kutcher and Cryer would find themselves starring together in Moore's 2019 memoir.

In "Inside Out," Moore recounted how Cryer fell head-over-heels for her after they appeared together in the 1984 movie "No Small Affair." She claimed that she took his virginity and would later regret the way their short-lived romance played out. "It pains me to think of how callous I was with his feelings — that I stole what could have been such an important and beautiful moment from him," she wrote (via Page Six).

In response to Demi Moore's lament that she had ruined his first sexual experience, Jon Cryer hopped on Twitter to correct the record in a self-deprecating, but sweet, way. "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," he wrote. In another tweet, 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."

While that was one load removed from Moore's conscience, on "The Howard Stern Show," Cryer did say that she broke his heart. He thought that he and Moore were exclusively dating until he showed up at her house one day and asked Moore's housekeeper where she was. "Her housekeeper said, 'She's out with her boyfriend,'" Cryer recalled. (Oof!) When he confronted Moore, she simply told him that she didn't think they were exclusive.

The saga of Cryer, Moore, and Ashton Kutcher took another bizarre twist when Cryer appeared on "Watch What Happens Live" with Scott Eastwood. While Cryer was talking about his ex, Eastwood interjected to spill some piping-hot tea: A woman Kutcher purportedly cheated on Moore with was Eastwood's girlfriend at the time.