11:58 PM EDT 05/24/2016

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Playboy Mansion

Holly Madison Opens Up About Rejoining the Dating Pool After Hugh Hefner Split

Originally posted 05/24/2016 11:50AM

Holly Madison is more than just a Girl Next Door.

After packing her bags and leaving the Playboy Mansion in 2008, Madison was ready to get back into the dating pool, but she feared that "outside judgment" about her past relationship would haunt her.

"I had just spent so many years living in fear of judgment and what other people think, and it was finally just letting go of that," Madison told PEOPLE Now. "It kind of set me free, so that was a big lesson."

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Credit: Richard Young/REX/Shutterstock
Playboy Founder Hugh Hefner Deposed in Sexual Battery Suit Against Bill Cosby, Lawyer Says

True Crime

Playboy Founder Hugh Hefner Deposed in Sexual Battery Suit Against Bill Cosby, Lawyer Says

Originally posted 05/20/2016 06:20PM

Playboy founder Hugh Hefner was deposed Wednesday in a sexual battery civil suit against embattled comedian Bill Cosby, according to a Los Angeles civil rights attorney.

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Holly Madison: Her Shame After Leaving Playboy, the 'Scarlet Letter' on Her Forehead and Fear She Wouldn't Find the One

Originally posted 05/11/2016 03:00PM

After seven years living in the Playboy Mansion with her former boyfriend Hugh Hefnerand his various other girlfriends, Holly Madison couldn't wait to start life on her own terms. But when she finally left the Mansion in 2008, she discovered her past would follow closely behind.

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Credit: Frazer Harrison/Getty
Hugh Hefner's Son Rails Against the Decision to Ban Nudity in Playboy

Bodywatch

Hugh Hefner's Son Rails Against the Decision to Ban Nudity in Playboy

Originally posted 02/11/2016 11:25AM

Hugh Hefner's son Cooper Hefner is frustrated with the decision to drop nudity from Playboy, which he says has put him at odds with the magazine's board.

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UpdatePosted 01/11/2016 07:50AM

Got $200 Million? The Playboy Mansion Officially Goes Up for Sale – but Hugh Hefner Will Still Live There

Originally posted 01/09/2016 07:20PM

Hugh Hefner's iconic home, the Playboy Mansion, has been listed for sale by Hilton & Hyatt and the Agency with an asking price of $200 million.

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Kendra Wilkinson's Dad: I've Wanted to Shake Hugh Hefner's Hand and Thank Him

Originally posted 10/15/2015 03:45PM

It's not a sentiment every father would have, but Kendra Wilkinson's dad Eric is utterly grateful to Hugh Hefner for taking in his daughter.

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Credit: REUTERS/Kevork Djansezian
Hugh Hefner's Son Cooper Engaged to Actress Scarlett Byrne

Hugh Hefner's Son Cooper Hefner Engaged to Actress Scarlett Byrne

Originally posted 08/07/2015 12:00AM

Cooper Hefner is proving to be much less of a Playboy than his father.

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Credit: Mike Windle/Getty; Amy Sussman/Invision/AP
Hugh Hefner's Son Blasts Holly Madison as a 'Gold Digger' | Playboy, Holly Madison, Hugh Hefner

Hugh Hefner's Son Blasts Holly Madison as a 'Gold Digger'

Originally posted 06/26/2015 02:45PM

Hugh Hefner's son is lashing out against his dad's ex, calling Holly Madison a flat-out "gold digger."

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Holly Madison Fires Back at Kendra Wilkinson and Hugh Hefner: 'I'm Definitely Not Rewriting History'

Originally posted 06/25/2015 04:15PM

A fight has been raging between two former Playboy bunnies in recent weeks, but the weapons of choice have been words, not pillows.

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Credit: Tasos Katopodis/Getty
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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