Ashton Kutcher and Demi Moore: Can Cougar Couples Work?

VIDEO: Chris Connelly reports on what has been going on with the super couple.
ABCNEWS.com

Can an older woman and a younger man ever really make it work?

Reports of Demi Moore and Ashton Kutcher's alleged marital discord have put a spotlight on the "Graduate"-style relationship, and shown that sometimes, like when your 33-year-old husband is accused of hooking up with a pretty young thing, it's not always pretty.

Click through to see how three other famous females have fared with veritable boy toys:

PHOTO: Cameron Diaz and Her Many Men
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Cameron Diaz, 39, and Justin Timberlake, 30

Did it work? No. Blonde and beautiful, Diaz and Timberlake were the couple to be from 2003 to 2007. Fittingly, they met at the Nickelodeon Kids' Choice Awards when Diaz was 30 and Timberlake was 22. The actress and the former boy band frontman fielded questions about their age difference throughout their relationship.

"It's not like this is the first time in the history of human relationships that people were drawn to one another because of who they are, not what age they are," Diaz told W magazine in 2004.

But a lack of desire for long-term commitment may have come between the two. In 2006, months before they broke up, Diaz went on Ellen DeGeneres' talk show and shared her feelings about getting married: "I'm a commitment-phobe. Don't want to do it."

The two remained on good enough terms to appear together in this year's comedy "Bad Teacher," but director Jake Kasdan dubbed their on-screen romp the "most uncomfortable sex scene in history."

PHOTO: Mariah Carey and singer Nick Cannon arrive at the 82nd Annual Academy Awards held at the Kodak Theatre in this March 7, 2010 file photo in Hollywood, Cali.
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Mariah Carey, 41, and Nick Cannon, 30

Did it work? Yes. It's easy to poke fun at Carey and Cannon. She named one of her twins after her favorite home decor theme. He spent $12,000 on a necklace that spelled out the kids' names in diamonds. They renew their wedding vows more often than most people renew their air fresheners. But beneath all the grandstanding, the couple appears to be genuinely in love.

"Everybody knows I'm obsessed with my wife," Cannon told People magazine earlier this month. "I'm married to Mariah Carey. It doesn't get better than that. I'd be an idiot to do anything wrong. I worship my wife. Have you seen my back? My back says 'Mariah Forever.'"

PHOTO: Portia de Rossi and Ellen DeGeneres arrive at COVERGIRL Cosmetics' 50th Anniversary Party held at BOA Steakhouse in this Jan. 5, 2011 file photo in West Hollywood, Cali.
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Ellen DeGeneres, 53, and Porta de Rossi, 38

Did it work? Yes. There's no man in this relationship. But that's the point. Short of stumbling on someone as devoted as Nick Cannon, for an older woman, the key to finding harmony with a younger spouse might be to seek out the fairer sex.

DeGeneres and de Rossi have been married since 2008, and now, they're eyeing a new partnership: a new comedy created by DeGeneres that will star de Rossi. If their relationship is any indication, it'll shine.

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