May 24, 2016 11:50 AM

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.”

Once she moved on from her relationship with the Playboy mogul, Madison admitted that she managed to break free of the label of “Hugh Hefner‘s ex-girlfriend.”

“It was kind of tricky, and I share a lot of dating stories. Names have been changed to protect the innocent,” the former Girls Next Door star joked. “I share a lot of stories because it was my first time out there as a single woman dating and I was really trying hard – even though I was doing a reality show at the time and I was in the public eye – to keep my dating life private.”

“I was tired of being associated with one other person and that has its own set of challenges,” the author adds, “so there was some crazy adventures and mishaps along the way.”

Madison, 36, is now happily married to events company owner Pasquale Rotella and mom to 3-year-old Rainbow with a son on the way.

She released her second memoir, The Vegas Diaries, on Tuesday.

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