Associated Press
| March 7, 2013

Demi Moore once led the pack as one of Hollywood’s most recognizable cougars, but after filing papers requesting spousal support from ex Ashton Kutcher this week, it's fair to say the actress is back on the prowl.

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And Moore isn't the only cougar to have lost a cub.

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“For cougar women who are in long-standing relationships, the hope is that the relationship has enough depth and breadth that it works, just as any seasoned marriage or committed relationship would as the years go by,” says Susan Shapiro Barash, author of "The Nine Phases of Marriage."

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Beverly Hills-based psychotherapist Dr. Fran Walfish adds that not all relationships with age gaps are doomed.

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“I think it is absolutely possible for some cougar relationships to work,” says Walfish. “Look at Goldie Hawn and Kurt Russell to see an example of a good working cougar relationship," she says. "It takes two willing partners who have emotional maturity to give and take successfully in a relationship.”

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So which Hollywood cougars weren't so lucky? Have a look:

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Halle Berry and Gabriel Aubry

In 2010, the 43-year-old actress Halle Berry and 34-year-old model Gabriel Aubry ended their relationship after being together for nearly five years.

PHOTOS: Halle Berry's Sexiest Moments

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Kim Cattrall and Alan Wyse

The 52-year-old “Sex and the City” star was famous for having her share of boy-toys on the series, but Kim Cattrall didn’t have that same magic touch when it came to real life.  The relationship between Cattrall and 30-year-old Alan Wyse ended after five years.

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Susan Sarandon and Tim Robbins

They were a lasting couple in Hollywood, at least until 2009 when 63-year-old Susan Sarandon and 51-year-old Tim Robbins parted ways after 23 years.

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Jennifer Aniston and John Mayer

A 39-year-old Jennifer Aniston began her relationship with 30-year-old musician John Mayer in 2008, but the two later split.

PHOTOS: Jennifer Aniston Turns 45, Has Not Aged Since 1995

Eva Longoria and Tony Parker

In 2008, 35-year-old “Desperate Housewives” star Eva Longoria confirmed that she filed for divorce from 28-year-old basketball player Tony Parker following claims that he cheated on her.

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Cameron Diaz and Justin Timberlake

Then 34-year-old Cameron Diaz and a 25-year-old Justin Timberlake met in April 2003After almost four years together, Diaz and Timberlake publicly announced their breakup in 2007.

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Sheryl Crow and Lance Armstrong

They may have dated for two years and engaged for nearly six months, but 43-year-old singer Sheryl Crow and 34-year-old cyclist Lance Amstrong called it quits in 2006.

PHOTOS: Lance Armstrong And Other Athletes Who Lost Their Endorsement Deals

Sandra Bullock and Ryan Gosling

In 2002, a 39-year-old Sandra Bullock began dating a 23-year-old Ryan Gosling. The couple parted ways a year later.

PHOTOS: Sandra Bullock Continues To Defy Aging