11:57 PM EDT 05/24/2016
Originally posted 05/24/2016 11:50AM
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."
Kendra Wilkinson Admits She Did 'Freak Out' a Little at the Overwhelming Response to That Stretch Mark Pic
Originally posted 05/13/2016 03:45PM
The Kendra on Top star joined the body-beautiful conversation on Mother's Day when she showed off her stretch marks in a photo captioned, "Look what my 2 babies did... They made me happy. #happymothersday."
Though the picture received tons of support, Wilkinson admitted to PEOPLE Now on Friday that she does get intimated by the huge response.
Kendra Wilkinson Blasts Holly Madison in Shocking Rant: She Wasn't Living in Fear [Having Sex With Hugh Hefner] for a Paycheck
Originally posted 05/12/2016 12:55PM
In an exclusive interview for PEOPLE, Madison revealed that she was in constant fear while living at the Playboy Mansion with former boyfriend Hugh Hefner.
"I was trying to sell this image of 'Oh everything is so great here,' but I was miserable inside," she said. "There was so much competition among the other women. I learned not to confide in certain people. There was a lot of fear."
On Thursday, Wilkinson, 30, stopped by PEOPLE Now and blasted her former Girls Next Door costar and her new book The Vegas Diaries, which details Madison's journey after she left the Playboy world.
Originally posted 04/08/2016 07:40PM
Keith Hefner, the younger brother of Playboy founder Hugh Hefner, died on Friday at his home in Beverly Hills at the age of 87.
Kendra Wilkinson on How She Managed to Date While Living at the Playboy Mansion: 'I Would Go to Hotels Down the Street'
Originally posted 03/30/2016 11:55PM
Kendra Wilkinson was put in the hot seat about her time at the Playboy mansion during Wednesday's Kocktails with Khloé
Originally posted 03/30/2016 11:30AM
In an exclusive sneak peek at Wednesday's Donnie Loves Jenny, McCarthy revisits the surprising place where she first dreamed of centerfold stardom – the Chicago convenience store where she worked for most of her teens.
Originally posted 03/07/2016 07:00PM
Crystal Hefner has been diagnosed with Lyme disease.
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.
Playboy Model Saw Chiropractor for Neck Pain Prior to Deadly Stroke but Not Medical Doctor, Family Says
Originally posted 02/05/2016 05:45PM
Playboy model Katie May, who passed away Thursday night at age 34, most likely had not gone to a doctor for her neck pain prior to her deadly stroke, her brother tells PEOPLE.
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