Though Hugh Hefner passed away in 2017 at the ripe old age of 91, the legendary magazine publisher has not been forgotten. As founder and Editor-in-Chief of Playboy for more than half a century, Hefner made a lasting (and often controversial) impact on the entertainment world. He also had a much-talked-about love life that featured a steady rotation of younger women, many not even half his age. So where are Hugh Hefner’s former partners now? Here’s a look at some of the publishing icon’s romantic relationships over the years.
Hefner began dating model and singer Barbi Benton in 1968. According to People magazine, the couple met on the set of the TV show Playboy After Dark when Benton was 18 and Hefner was 42. During the course of their relationship, Benton appeared on four Playboy covers and lived with Hefner at his famed Playboy Mansion in Los Angeles. Though the pair broke up in 1976, they remained close friends until his death. “When he died, he took a big piece of me with him,” Benton told People in a 2017 interview. “I’m sure that every time I do something, I’ll think about having done it with Hef. He had an enormous impact on the culture and lives of people all over the world. I’ll miss him immensely.”
Benton has been married to real estate developer George Gradow since 1979. The couple has two grown children and currently lives in Colorado.
Hugh Hefner married his second wife, Kimberley Conrad, in 1989. Conrad, who had just been named Playmate of the Year, was 36 years his junior. The couple went on to have two sons together—Marston Glenn in 1990 and Cooper Bradford in 1991. Though Conrad and Hefner separated in 1998, they stayed legally married until 2010, with Conrad living in a house just next door to the Playboy Mansion. “I would’ve been happy to divorce her when we separated,” Hefner told People magazine when he eventually filed for divorce. “But she wanted to remain married for our boys.”
Getting divorced from Hef didn’t banish Conrad from the pages of Playboy, however. In 2017, after their son Cooper became CEO of the Playboy brand, Conrad once again appeared on the magazine’s cover.
Actress and model Brande Roderick was Playboy’s Playmate of the Year in 2001. She also dated Hefner from 2000 until 2001. The starlet appeared in a number of TV shows and movies during the 2000s, including Starsky & Hutch, Snoop Dogg’s Hood of Horror, Club Wild Side 2, The Nanny Diaries. The Parkers, Just Shoot Me!, and Fear Factor.
In 2007, Roderick married NFL star Glenn Cadrez. The couple has two sons together but divorced in 2017. Today, Roderick describes herself as a “mother, actress, author, and realtor” in her Instagram bio. She currently hosts a weekly series called “At Home With Brande” on YouTube, which features her in her everyday life.
When it comes to Hugh Hefner’s partners, Holly Madison is perhaps one of the most well-known. Beginning in 2001, she was in a seven-year relationship with the publisher as one of the three girlfriends living with him at the Playboy Mansion. Along with Bridget Marquardt and Kendra Wilkinson, Madison appeared on the E! reality show The Girls Next Door, which followed the trials and tribulations of Hefner’s trio of women.
Though Madison and Hefner broke up in 2008, Madison remained on The Girls Next Door for some time after their split. She then went on to star in her own reality show, Holly’s World, which ran for two seasons. She’s also written two memoirs that have been New York Times bestsellers—Down the Rabbit Hole: Curious Adventures and Cautionary Tales of a Former Playboy Bunny and The Vegas Diaries: Romance, Rolling the Dice and the Road to Reinvention. She still works regularly and has a healthy 1.1M followers on Instagram.
Madison married film producer Pasquale Rotella in 2013—they have two children together. Sadly, Madison and Rotella separated in 2018 and finalized their divorce in 2019.
Another member of The Girls Next Door girlfriend gang, model Bridget Marquardt began dating Hef after moving into the Playboy Mansion in 2002. In addition to the E! reality show, she appeared in a number of movies and TV shows, including Curb Your Enthusiasm, Entourage, The House Bunny, The Apprentice: Los Angeles, and Celebrity Paranormal Project. The later show piqued her interest in the supernatural and led Marquardt to become a private paranormal investigator. Since 2019, she’s been hosting the podcast Ghost Magnet with Bridget Marquardt, which features the model’s adventures exploring paranormal phenomena.
After moving out of Hefner’s mansion in 2009, Marquardt became involved with director Nicholas Carpenter and the pair eventually moved in together.
Also well-known for being one of Hugh Hefner’s girlfriends on The Girls Next Door, model Kendra Wilkinson met the Playboy magnate in 2004 after attending his 78th birthday party. Almost immediately, Hef asked her to join the reality show trio and move into the Playboy Mansion. “I was like, ‘Hell yeah, I’m here!’” Wilkinson told the New York Post in 2014. “I was living in this small-ass apartment with this ugly-ass bitch. I was praying for anything to get me out of there. I moved in and weeks went by and I didn’t know that sex was involved. I knew nothing about Playboy, I’d just graduated high school.”
After five years, Wilkinson moved on from Hef and out of the Playboy Mansion to star in her own reality show, Kendra. The show was a huge hit and with 2.6 million viewers, the premiere episode became the highest-rated reality show for the E! network at that time. The first season of the show followed the model as she planned her wedding to her new love, NFL star Hank Baskett. Kendra went on to air for four seasons total and spawned a spin-off, Kendra on Top, which lasted from 2012 until 2017. During that time, Wilkinson and Baskett had two children together. The couple divorced in 2018.
More recently, Wilkinson made headlines when former The Girls Next Door co-star Holly Madison insinuated Wilkinson was lying about not knowing that sex was involved in living with Hef at the Playboy Mansion. “I’m not trying to slut shame anybody or anything,” Madison said, “but nobody ever got asked to move in unless they had slept with him.”
In response, Wilkinson made it clear that she has more important things in her life to worry about than her days as a Girl Next Door. “Dude… it’s 2021,” she wrote on Instagram. The model followed the comment by saying, “Times have changed. I forgive and have kids to love and focus on.”
When she started dating Hefner in 2009, Crystal Harris was 60 years his senior. She became Hef’s third wife in 2012, after initially breaking off their engagement five days before they were supposed to marry in a lavish ceremony. Despite the initial drama, Harris remained married to Hefner until his death in September if 2017 and ended up inheriting a big chunk of his fortune. When he died, Harris described her husband as, “A pioneer. A kind and humble soul who opened up his life and home to the world.”
In 2021, Harris shared via Instagram that she nearly died as a result of a fat transfer surgery she had undergone in the fall. The experience has led her to speak out about society’s unrealistic beauty standards.
“How our culture defines beauty makes it impossible to keep up with, she wrote. “Women are overly sexualized. I know from the worst kind of experience. For ten years my value was based on how good my physical body looked. I was rewarded and made a living based on my outer appearance. To this day I need to write reminders of why I’m worthy that have nothing to do with my physical appearance to convince myself that I’m enough.”
The Shannon Twins
Karissa and Kristina Shannon dated Hugh Hefner began living with Hefner in 2008 at the tender age of 18. They lived with him for three years, and can also be seen on the TV show The Girls Next Door. They recently opened up about their experience with Hefner and claim to have PTSD from their experience. It has been revealed they were only 17-years-old when they posed for the Playboy magazine.
The Shannon twins are still recovering from their experience. They reported to Radar, “We weren’t allowed to even talk to other men and we were forced to smile when he started noticing our depression.”
The twins are now pursuing acting careers and have an OnlyFans.