02:33 PM EDT 07/10/2016
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."
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.
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.
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.
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.
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.
Originally posted 08/07/2015 12:00AM
Cooper Hefner is proving to be much less of a Playboy than his father.
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."
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.
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.
The most buzzed about stars this minute!
Treat Yourself! 4 Preview Issues
More On PEOPLE.com
Got a News Tip?
Send it to our People.com editors!