Jon Cryer: Dating Demi Moore Made Things Awkward With Ashton Kutcher On ‘Two And A Half Men’

Jon Cryer wants you to know that he’s one lucky Duckie — during a recent interview, he revealed that he once dated one of Hollywood’s hottest women. However, during the same interview, he lost a few cool points by admitting that he once hired a prostitute.

You might be surprised to learn that Jon Cryer dated Demi Moore after meeting the beautiful brunette on the set of the 1984 movie No Small Affair. Demi would go on to get married to and divorced from Jon’s Two and a Half Men costar Ashton Kutcher. However, Jon recently told Entertainment Tonight that he wasn’t sure whether Demi ever bothered telling Ashton about their fling.

“It was awkward in that I’m not sure she even told him that we dated. 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.”

During an interview with Good Day New York, Jon Cryer described his relationship with Demi Moore as a “whirlwind” romance. The relationship probably didn’t last very long — Cryer confessed that he barely remembers it.

“I don’t know how that happened. I don’t remember it. She was already a star. It was kind of this whirlwind for me… and then suddenly she kissed me…I was very young.”

If the fling wasn’t very memorable for Jon, perhaps it was the same way for Demi Moore. It’s possible that she didn’t tell Ashton Kutcher about the relationship because she completely forgot about it.

Cryer has been talking about his past quite a bit lately because he’s busy promoting his new book, So That Happened: A Memoir. As the Inquisitr previously reported, Cryer’s autobiography is full of tawdry tales about the exploits of his rock star from Mars Two and a Half Men costar Charlie Sheen. However, it also features some interesting stories about Cryer’s earlier career, including a few from his time working on the beloved John Hughes’ movie Pretty in Pink. Nostalgic fans might think that Jon was the perfect pick to play forever-friend-zoned, dorky Duckie, but Molly Ringwald was upset that Jon’s role didn’t go to Robert Downey, Jr.

Speaking of Pretty in Pink, Jon Cryer recently got to relive his Duckie days during a game of celebrity shades. In the clip below from The Tonight Show with Jimmy Fallon, Michael Douglas proves that he doesn’t know much about Jon’s early work.

During an interview with CBS Sunday Morning, Jon Cryer’s wife, Los Angeles TV reporter Lisa Joyner, revealed that the actor almost became her Duckie in real life. She and Jon got married in 2007, but she didn’t see him as relationship material at first.

“I thought he was going to be my new best gay friend,” Joyner revealed. However, she changed her mind after she and Jon got to know one another and shared their first kiss.

Jon Cryer did something that he’s not exactly proud of before winning his happy ending. He went through a tough time after his divorce from Sarah Trigger in 2004, and he dealt with the demise of his marriage in a very Charlie Sheen way: he hired a prostitute. In his memoir, Cryer writes about using a call girl for companionship. He knew that the story would get a lot of attention online, so he decided to have a talk with his son about the embarrassing incident before the kid saw it splashed all over the internet.

“I found myself picking my son up at school and having to give him a heads up that, ‘Oh, you might read something on the Internet today that’s a little curious. So I told him the facts of it, and he said, ‘Yeah, I’m not surprised.’ I was like, ‘Wow, okay!'”

Are you more surprised that Jon Cryer dated Demi Moore or that he hired a prostitute?

[Image credits: Alberto E. Rodriguez, Mark Davis/Getty]