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Jon Cryer reveals he dated Demi Moore 30 years before his Two And A Half Men co-star Ashton Kutcher married her

Published: 13:34 EST, 7 April 2015 | Updated: 15:13 EST, 7 April 2015

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Jon Cryer dated Demi Moore some 30 years before she married his Two And A Half Men co-star Ashton Kutcher.

The 49-year-old actor made the revelation in his juicy new tell-all memoir So That Happened.

Jon admitted it made for a rather awkward moment when Ashton turned up for 'chemistry meetings' to see if he would be a good replacement for Charlie Sheen after he quit CBS's hit sitcom Two And A Half Men in 2010.

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Laughing about it now: But Jon Cryer revealed on Tuesday he felt awkward when Ashton Kutcher was being cast for Two And A Half Men in 2010 because he had dated the star's wife, Demi Moore, in the 1980s

The way they were: Jon met Demi when they co-starred in 1984's No Small Affair - and life soon imitated art

On sale now: Jon's memoir So That Happened

Jon, who turns 50 on April 26, met Demi, 52, when they both starred in 1984's No Small Affair.

'How do I tell Ashton she and I dated when he was seven?' he recalled on Live! With Kelly And Michael on Tuesday morning.

He said he spent he whole time on tenterhooks waiting for the bomb to drop.

But he needn't have worried. 'At the end he said, "She told me." He was cool about it.'

At the time, Ashton and Demi were married. They split In November 2011 after six years together and finalized their divorce in November 2013.

Jon, who is now married to Lisa Joyner, told Kelly Ripa he approached Charlie when he decided to write what he called his 'comedy' book.

'He let me print the emails he sent calling me a troll, turncoat and a traitor' for continuing in the CBS sitcom after he left, indicating that pair have rebuilt burnt bridges.

The star explained his new shaved head look, saying: 'I did it because I could.

A dfferent kind of proposal: Jon told Live! With Kelly And Michael on Tuesday that Ashton let him sweat before admitting that Demi had already told him about their romance

She's my wife: Ashton and Demi, pictured at a Hollywood event in 2011, were still together when he joined the cast of Two And A Half Men

There's this freedom that you don't have for 12 years when you have to look the same for a show,' adding that Lisa called it his 'terrorist look' when he grew some designer stubble

Jon, who shot to fame in 1986's Pretty In Pink, also talked about taking Charlie's advice on hookers when he divorced first wife Sarah Trigger in 2004, in an excerpt printed by The Hollywood Reporter.

'My forays into prostitution were about as awkward as you might imagine,' he wrote. His first time 'was really a very friendly experience' that happened at his home.

Building bridges: Charlie Sheen quit Two And A Half Men in 2010, calling Jon a 'troll, turncoat and a traitor' for staying on the show. But he agreed when Jon asked permission to use his insulting emails in his memoir

Finding fame: Jon was one of the co-stars in the now iconic teen movie Pretty In Pink in 1986

'The next time, I went to her place. We sat down, tried to make small talk and halfheartedly stumbled into a conversation about recent fluctuations in the stock market,' wasting half of his hour.

Jon is making the round of chat shows to promote his memoir, revealing funny stories during appearances on Entertainment Tonight and The Tonight Show With Jimmy Fallon on Monday, among others.

So That Happened is on sale now.