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Ashton Kutcher, Demi Moore, Jon Cryer

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Hollywood is a very small town.

In his newly released memoir, So That Happened, Jon Cryer revealed that he once romanced his Two and a Half Men co-star Ashton Kutcher's ex-wife, Demi Moore. Jon, 49, recalled that he and Demi, 52, dated 30 years ago, around the time that they co-starred in the 1984 romantic comedy No Small Affair.

When Ashton, 37, replaced Charlie Sheen on CBS' Two and a Half Men in 2011, Jon was afraid to tell him that they shared a mutual ex. "It was awkward in that I'm not sure she even told him that we dated," the actor told Entertainment Tonight Monday. "In our first meeting, we're trying to have that let's-create-that-chemistry meeting, and the whole time I'm looking at him, waiting for him to drop the bomb."

On Live! With Kelly and Michael Tuesday, Jon shared new details about his fling with Demi. "It was a little bit awkward because she and I had dated when he was 7, so there was that aspect," he joked.

"I don't know if you recall, but this was during the firestorm of all the craziness when Charlie Sheen left the show and he was a possible guy taking over, so we had a meeting to see how it would go," he said.

Before Ashton arrived for the chemistry meeting, Jon was nervous. "I didn't know if she had even told him that we had dated, so for the whole meeting, he didn't say anything," the Pretty in Pink actor said. "Every time he'd make a joke, I'd be kind of awkward, like, 'Ha, ha, ha! That's a great joke! Because we're old friends, you know? It's not like I dated your wife!' It was a very awkward meeting, but at the very end of it, he said, 'She told me. It's cool. Don't worry about it.'"


Jon was married to Sarah Trigger from 1999 to 2004; they share custody of their teenage son, Charlie Austin Cryer. Jon married Lisa Joyner in 2007; they adopted a daughter, whom they named Daisy Cryer.

Demi announced her separation from Ashton in 2011, and the actor filed for divorce the following year. The former couple, who had a 16-year age gap between them, finalized their divorce in November 2013.