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 / Updated  / Source: TODAY
By Erin Clements

Jon Cryer and Ashton Kutcher played roommates on "Two and a Half Men," but Cryer recently revealed that the pair have another common thread.

In his new memoir, "So That Happened," Cryer reveals that 30 years ago, he dated Kutcher's ex-wife Demi Moore after he and the actress co-starred in the 1984 flick "No Small Affair."

In the film, Cryer played a teenage photographer who falls in love with a 22-year-old woman after taking a picture of her.

Demi Moore and Jon Cryer star in "No Small Affair"
Demi Moore and Jon Cryer starred in "No Small Affair" in 1984.1984 Columbia Pictures Industrie

The romantic relationship made for an uncomfortable moment when Cryer first met Kutcher, who joined his hit sitcom in 2011 as Charlie Sheen's replacement.

"It was awkward in that I'm not sure she even told him that we dated," Cryer, 49, told "Entertainment Tonight."

"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," he added.

Cryer's trip down memory lane had us reminiscing about what other celebrities were once an item. Here are some of our favorite forgotten pairings:

Moby and Natalie Portman

Moby and Natalie Portman in 2001
Moby and Natalie Portman in 2001Theo Wargo / WireImage file

The electronic-music pioneer told Spin that his 2001 fling with the actress made him "the target of a lot of nerd wrath." He added, "You can’t date Luke Skywalker’s mom and not have them hate your guts."

Ryan Reynolds and Alanis Morissette

Ryan Reynolds with Alanis Morissette at the premiere of "Blade Trinity"
Ryan Reynolds with Alanis Morissette in 2004Frazer Harrison / Getty Images file

The "You Oughta Know" singer was engaged to the actor for two years before parting ways in 2006. In 2005 she told People, "He's just such a supportive creature. I feel so loved by him, in a trampoline kind of way. He's always very happy for me."

Tom Cruise and Cher

Tom Cruise and Cher in 1985
Tom Cruise and Cher in 1985TRIPPETT/SIPA/ Sipa USA

The "Believe" singer told Andy Cohen that Cruise — whom she dated in the mid-'80s — was one of her "top five" lovers.

Giuliana Rancic and Jerry O'Connell

Jerry O'Connell and Giuliana DePandi (now Rancic)
Jerry O'Connell and Giuliana Rancic in 2003Frazer Harrison / Getty Images file

Rancic dated O'Connell from 2003 to 2004, and dished out details about the relationship in her new memoir.