Jon Cryer Dated Demi Moore Decades Before She Wed Ashton Kutcher

Kutcher became the frontrunner to take over the lead role from Charlie Sheen after he was fired from the sitcom in 2011 following a public feud with executive producer Chuck Lorre, but Cryer feared he wouldn't be able to get along with his potential new co-star because of their unlikely connection.

The Pretty In Pink actor recalls, "It was a little awkward because she (Moore) and I had dated when he (Kutcher) was seven! There was that aspect, but what happened was, we had our very first meeting... but I didn't know if she had told him we had dated, so for the whole meeting, he didn't say anything, so every time he'd make a joke, I'd be kind of awkwardly like..., 'Ha ha ha, that's a great joke, 'cause we're old friends; it's not like I dated your wife!'

"At the very end of it, he said, 'She told me. It's cool, don't worry about it'."

Cryer, 49, and Moore, 52, dated briefly after co-starring in 1984 film No Small Affair.

The actress was 42 when she wed 27-year-old Kutcher in 2005, but they divorced in 2013.