How Holly Madison Rebuilt Her Life After Hugh Hefner–and How She’s Rebuilding All Over Again

Holly Madison knows a thing or two about reinvention.

A decade ago, the former Girls Next Door star stunned fans of the Playboy-centric series when she announced that her time as one of Hugh Hefner‘s girlfriends had come to its end—though, as it later played out on the fifth season of the E! series, 2008 was a time of transition for all of Hef’s girls. But none more so than for Madison, who finally had to let go of whatever dream she once had of making an honest man out of the legendary publishing icon and set out on finding her own path. (His admitted inability to have children, too, proved to be a non-negotiable for her.)

So, she hightailed it out of Los Angeles for Las Vegas and began to build a world of her own. (Naturally, her spinoff series, which ran on E! for two seasons, was called Holly’s World.)

“I moved into the Playboy mansion right when I was in the middle of college. I didn’t date like a normal person in my 20s; I wasn’t pursuing a normal career or getting to know myself in the ways that most people do when they’re in the real world,” she told Broadly in 2016. “When I moved out at age 29, I felt like I was coming out of college almost. I was having the experiences that most people have in their 20s—finally.”

And it was there, in Sin City, where Madison, who turns 39 on December 23, began to finally build a career of her own. Following a stint on Dancing With the Stars, she landed a gig as the star of Planet Hollywood’s burlesque show Peeshow, replacing Kelly Monaco after her three-month contract was up. What was intended as a similarly 90-day deal wound up being extended and extended further owing to her popularity in the role. And as she lived life as Miss Las Vegas, ruling over the Strip for a period of time when such a thing was possible for someone who wasn’t either a pop diva or powerhouse DJ, she was also out in them streets.

She had dalliances with Criss Angel, (reportedly) Russell Brand, and Benji Madden, the latter of whom, perhaps because she’d learned her lesson from letting her prior relationships play out so publicly, she did her darndest to make sure didn’t get caught up in her Holly’s World docu-series, refusing to even talk about him during interviews on the show. (It didn’t work—as she revealed in her New York Times bestseller The Vegas Diaries, someone on production went behind her back to try and get his people to allow him to appear on the show, effectively ending the relationship then and there.)

But aside from being tell-all fodder for her down the road, these moments of Madison feeling her oats were just that: An opportunity for a woman breaking out of an unconventional and, as she’d later reveal, stifling situation to figure out exactly what she did and did not want. Not that it was easy, mind you. 

“You don’t wanna ask somebody you just met, ‘Oh do you wanna be in my reality show today?’ Because that just doesn’t lead to a healthy relationship necessarily,” Madison told uinterview.com in 2016. “When I was finally single and dating I had a lot of paranoia about: why do people wanna date me? Do they wanna date me because I’m on TV? Or do they wanna date me because they wanna brag to their friends that, ‘Oh I’m dating the girl on that billboard?'”

And in 2011, she met Pasquale Rotella, whose company Insomniac hosts the Electric Daisy Carnival every year out on the Las Vegas Speedway. A relationship that began online, mostly on Twitter, soon led to a feeling that they were “inseperable,” as she noted in her first memoir Down the Rabbit Hole, calling him “the total package” and her “Prince Charming.”

By the following year, as Hefner was tying the knot to new girlfriend Crystal Harris—a sudden about face from the man who always told her he couldn’t commit to marrying her, which left her “very surprised,” as she told E! News—she was pregnant and ready to leave Peepshow behind. Daughter Rainbow Aurora  arrived on March 5, 2013, followed by an engagement announcement three months later. “I got engaged on Sunday!” she wrote on her blog, sharing photos of the 40-carat ring with a cushion-cut yellow diamond center stone surrounded by pink and yellow diamond flowers. “He proposed to me at the top of the Ferris wheel at [Electric Daisy Carnival in] Las Vegas. I was so happy that so many of our close friends were there to share the wonderful moment with us! We rode around the festival on the art car until the sun came up!”

They tied the knot three months later with a fairy-tale wedding held at their destination of choice, Disneyland. The park shut down early for the special occasion, with the ceremony being held at the Blue Bayou restaurant inside the Pirates of the Caribbean ride shortly after 9 p.m. Nearly 150 people were present to witness the event, including their daughter Rainbow Aurora and Madison’s former Girls Next Door co-star Bridget Marquardt, who served as one of her bridesmaids. “It was just amazing,” she told E! News a week later. “We had our own Fantasmic! showing and we had the reception in New Orleans Square.”

So, with her happily ever after seemingly on track and her time on the Las Vegas Strip firmly in her rear view, it was time to think, yet again, about rebuilding her life. And what emerged was Holly Madison, the author. 

“I got tired of people approaching me and thinking they knew my story,” she told Broadly of the impetus for putting pen to paper. “It got frustrating when I was on my own in Vegas and people would approach me and say, “Don’t you miss the mansion? Sorry didn’t things work out!” You don’t have to pity me. Things are going better than ever. I wanted to share that side of the story.”

And boy, did she.

Her first memoir, 2015’s Down the Rabbit Hole: Curious Adventures and Cautionary Tales of a Former Playboy Bunny, left no stone unturned in her quest to illuminate the general public on what life was really like inside the Playboy Mansion while she was there. Debuting at No. 1 on the New York Times Bestseller list, the book had plenty of fans, keeping it on the list for three months that year. Not among them? Hefner and fellow former Girls Next Door star Kendra Wilkinson. Amid Madison’s allegations that Hef had been a manipulator who “pitted” the girls against one another, that he offered her drugs and was verbally abusive, and kept his bedroom in a Hoarders-esque state of disarray, among many other things, Hefner issued a statement that claimed his former No. 1 girl was attempting to rewrite history “in an attempt to stay in the spotlight.” (His son, Cooper Hefner, took it further, labeling Madison a “gold digger” painting herself as “a victim of a relationship [she] aggressively sought out.”)

Meanwhile, Wilkinson, at the time starring on a series of her own, Kendra On Top, said that she and Madison “were never friends”—’At the end of the day, what we did was we just f–ked the same man”—as she staunchly defended Hefner, asserting, “She doesn’t have facts.”

The blowback didn’t faze Madison one bit. “I don’t even care what his reaction is to this,” she told E! News. “I’m doing this for me and I’m doing this so people can learn from my mistakes.” And with the response to the book as enthusiastic as it was, she quickly followed it up with her second, 2016’s The Vegas Diaries: Romance, Rolling the Dice and the Road to Reinvention.

While this tome focused more on life after the Mansion, detailing the years spent starring in Peepshow and Holly’s World, she didn’t skimp on the Hef content, either. And that prompted another round of feuding with Wilkinson, who unleashed a (since-deleted) vulgar Twitter tirade, accusing Madison of being “in fear knowing so many of us saw her doing some nasty s–t,” among many, many other things.

And while the court of public opinion was decidedly split on who they believed, with Madison’s story predating our current #MeToo-Time’s Up world, the former Playmate chose to stay above the fray when Wilkinson and other critics came for her, focusing instead on her family. Pregnant with her second child, at the time of The Vegas Diaries‘ release, she welcomed son Forest Leonardo into the world on August 7, 2016. And things between her and her husband seemed pretty, well, fairy-tale-y. 

“Oh, there’s so many great things about him, I don’t know where to start,” she gushed to Cosmopolitan that year when asked what made Rotella a good man for her. “He’s a really amazing, solid person, and I think we met just at the right times in our lives where he was ready to settle down, and where I had felt like I finally found myself and was OK with myself, and it was just magic.”

A year later, she was explaining to the Las Vegas Review-Journal that she was was happy with the way in which real romance and marriage came into her life. “I feel like that’s what I was always looking for all along, but, as I was growing, you learn that you have to find yourself first,” she said. “The right person isn’t going to come along until you’re confident, until you’ve gone out there and lived life. I’m glad that it happened that way.”

But sadly, the magic soon proved to not be enough, as the couple filed for divorce on August 31, 2018, just days shy of her fifth wedding anniversary. And while Rotella spoke out on Instagram after the news broke, assuring that he and his now-ex would “remain the best of friends while co-parenting and continuing to support one another in our respective passions in life,” Madison has yet to break her silence on the split. Much like when Hefner passed away the year prior, there has been no social media posting or statement from a publicist expressing Madison’s wishes or stance.

With Madison returning to Los Angeles as her home base post-split, as sources confirmed following the reveal, it’s clear that she finds herself, yet again, in one of those reinvention stages she knows all too well. And while it’s hard to say what, exactly, the future holds in store for her, one thing’s for sure: She knows a thing or two about reclaiming control over her life.

After all, she did write of Rotella in Down the Rabbit Hole, “He’s my prince charming, but I didn’t need saving. I saved myself.”

There’s no doubt she’ll do it again.

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