From when you were dating Ashton Kutcher.

We all knew that there was a big age gap between Demi Moore, 52 and Ashton Kutcher, 37 when they started dating in 2003. But we thought it was a hurdle they would conquer after their marriage in 2005 and were sad it didn’t work when Kutcher filed for divorce in 2012.

But now that age gap has become even more prominent after Moore’s previous dating life with one of Kutcher’s co-stars was revealed.

Moore previously dated Kutcher’s Two-and-a-Half Men co-star Jon Cryer, 49, nearly 30 years before she met her younger beau. The ‘older’ pair got together when they appeared in No Small Affair, a movie from the 80’s.

The juicy gossip came to light from Cryer's new memoir titled, So That Happened.

The actor spoke to etonline about the moment Kutcher started on Two-and-a-Half Men with him and how awkward he found it to try and break the ice around his dating history.

The ET host said, "Flash forward and Ashton Kutcher joins Two-and-a-Half Men," with which Cryer responds, "Awkward."

"It was awkward because I didn't know if she'd even told him that we'd dated," he told the host.

Ashton Kutcher and Jon Cryer on Two and a Half Men.

Cryer also spoke to Live! With Kelly and Michael and said he didn't know how to broach the subject.

"How do I tell Ashton she and I dated when he was seven?" he told the Live! host.

Luckily Kutcher was good about it - Cryer told the television host that Ashton said, "She told me." And all was ok.

Kutcher and Moore were married for six years. Kutcher is now with Mila Kunis and the two have a baby girl, Wyatt together. Kutcher and Cryer played characters that were bestfriends and housemates in Two-and-a-Half Men - the show finished in February this year.

What do you think of dating a man or woman much older or younger than you?

CLICK THROUGH the gallery two Ashton Kutcher with his young family now...

Mila Kunis and Ashton Kutcher.

Ashton and Mila

A Mila Kunis and Ashton Kutcher montage.

Hiding out.

A throw back to Mila Kunis and Ashton Kutcher in the younger days.

Mila Kunis and Ashton Kutcher getting friendly with a mascot.

High fives. Winning.

Ashton and Mila

Blue baby belly.

Mila Kunis and Ashton Kutcher, what's the surprise?

All country.

Natural models.

Ashton and Mila

What are you looking at guys?

A retro Ashton Kutcher and Mila Kunis.

Ashton and Mila

Montage.

So cute. Adorable.

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"Ashton Kutcher reveals the inspiration behind his baby daughter's unusual name."

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