12:06 PM EDT 08/26/2015

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Hugh Hefner

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Holly Madison 'Has No Regrets' About Time with Hugh Hefner, Source Says

Holly Madison 'Has No Regrets' About Time with Hugh Hefner, Source Says

Originally posted 06/12/2015 04:05PM

Despite her dark time in the Playboy Mansion, Holly Madison doesn't regret dating Hugh Hefner, a source close to her tells PEOPLE.

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Inside the Playboy Mansion: Holly Madison Details Orgies – and Fertility Treatment with Hugh Hefner

Inside the Playboy Mansion: Holly Madison Details Orgies – and Fertility Treatment with Hugh Hefner

Originally posted 06/10/2015 02:55PM

Facing homelessness in Los Angeles, aspiring actress and model Holly Madison turned to Hugh Hefner and the Playboy Mansion for sanctuary, she reveals.

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Holly Madison Hasn't Spoken to Kendra Wilkinson in Years Following Bitter Feud: 'I Don't Miss Her'

Holly Madison Hasn't Spoken to Kendra Wilkinson in Years Following Bitter Feud: 'I Don't Miss Her'

Originally posted 06/10/2015 10:50AM

Holly Madison reveals in her new memoir Down the Rabbit Hole: Curious Adventures and Cautionary Tales of a Former Playboy Bunny that she hasn't spoken to Kendra Wilkinson since an explosive feud separated them for good.

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Holly Madison: I Wanted to Kill Myself at the Playboy Mansion

Holly Madison: I Wanted to Kill Myself at the Playboy Mansion

Originally posted 06/10/2015 09:35AM

Holly Madison contemplated drowning herself in the bath at the Playboy Mansion in the depths of her despair as Hugh Hefner's No. 1 girlfriend, she reveals.

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Holly Madison Contemplated Suicide While Living in the Playboy Mansion

Holly Madison Contemplated Suicide While Living in the Playboy Mansion

Originally posted 03/23/2015 02:00PM

She shared her life on The Girls Next Door, but Holly Madison has been hiding a secret … until now.

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Kendra Wilkinson 'Feels Like Such a Fool' About Hank Baskett's Alleged Cheating

Kendra Wilkinson 'Feels Like Such a Fool' About Hank Baskett's Alleged Cheating

Originally posted 07/16/2014 04:00PM

Since news broke that her husband Hank Baskett allegedly cheated on her earlier this year with a transexual model, Kendra Wilkinson has been spotted several times without her wedding ring.

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Check Out Kate Moss as a Playboy Bunny!

Kate Moss Wears Playboy's Bunny Costume

Originally posted 11/13/2013 06:30PM

Kate Moss makes one sexy rabbit! The supermodel dons Playboy's legendary bunny costume to commemorate the magazine's 60th anniversary.

"She's a worldwide celebrity and iconic and crosses the boundaries from sexual imagery to upscale modeling," Playboy founder Hugh Hefner told the Los Angeles Times in September about why Moss was chosen for their sixth decade cover.

The magazine hits stands in January 2014, the same month Moss turns 40.

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Who Should Courtney Stodden Date Next? We Decide! | Courtney Stodden, Doug Hutchison

Who Should Courtney Stodden Date Next? We Decide!

Originally posted 11/06/2013 07:00PM

Adolescence is a confusing time. One moment you want to be married; the next, you don't. Or so it was for Courtney Stodden, who after two years of marriage, decided to part ways with former Lost star Doug Hutchison, her husband and elder by 35 years.

Wed at the age of 16, "Now, at 19, she's interested in exploring life as an unmarried single young adult – with the freedom to explore her independence," her rep told the U.K.'s Daily Mail. Without reading too much into that loaded statement, we're going to assume a return to dating is on the horizon for the aspiring country singer, and given her past preferences, we've narrowed down our suggestions by age range. Meet your matches, Courtney!

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Crystal Hefner's Parents 'Love' Her Playboy Lifestyle

Crystal Hefner's Parents 'Love' Her Playboy Lifestyle

Originally posted 05/13/2013 05:30PM

If anyone's okay with Crystal Hefner being married to a man three times her age, it's her parents.

Her mom and dad are not just supportive of her relationship with Playboy mogul Hugh Hefner, they also enjoy the chance to reap the benefits of her lavish life.

"My parents come up here pretty much every weekend," Crystal, 26, told PEOPLE on Thursday at the Playboy Mansion, just before her husband, 87, announced Raquel Pomplun as 2013's Playmate of the Year.

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What Did Crystal Harris Get Hugh Hefner for His 87th Birthday?

Crystal Harris Shares the Birthday Gift She Got Hugh Hefner

Originally posted 04/11/2013 08:00PM

Age is nothing but a number for Hugh Hefner, who isn't showing signs of slowing down after turning 87 on Tuesday.

Part of what might keep him youthful? Having Crystal Harris, 26, as his wife.

"I'm having the time of my life," Harris gushed on Thursday to KTLA. "He's an amazing man, such a romantic. For Valentine's Day, he was like, 'What kind of flowers do you like? Do you like roses? Do you like mixed flowers?' I like everything, so he got me everything … He's just so sweet."

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