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Kendra Wilkinson
Getty Images (2)Former Playboy model and reality star Kendra Wilkinson he is no stranger to the public eye.
The 39-year-old first turned heads in 2004, when she attended a late Playboy publisher Hugh Hefner78th birthday party. Shortly after the event, she was asked to move into the iconic Playboy mansion and started dating Hefner.
“Hef asked me to be one of his girlfriends, and live in the mansion and I was like, ‘Hell yeah, I’m here!'” the California native recalled. I’m Famous, Get Me Out of Here! in 2014. “I was living in this little ass apartment with this ugly ass whore. I was praying for anything to get me out of there. … I moved in and weeks went by and I didn’t know there was sex involved. I knew nothing about PlayboyI had just graduated high school.”
Wilkinson’s relationship with Hefner — along with his concurrent relationships with exes Playboy models Holly Madison a Bridget Marquardt — documented in the hit E! Reality series The Girls Next Door. The reality series premiered in August 2005 and ran for five seasons. All three romantic relationships ended in 2008.
Since then, Wilkinson has appeared on several television shows, incl Entourage, How I Met Your Mother a Scary Movie 4. She has also written two books and starred in her own reality TV show, Kendra on Topwhich documented her relationship with a former NFL receiver Hank Baskett. (The pair married in 2009 and welcomed two children before divorcing in 2018.)
In 2025, Wilkinson made headlines after fiercely protect her weighttells the naysayers that she is “not that girl I used to be.”
“Yes, I have gained weight. Yes, I’m getting older,” Wilkinson wrote via Instagram on January 12. “Yeah, I’m not the girl I used to be (play girl) but for once in a long time I feel good and mentally healthy.”
Read on for some of Wilkinson’s most memorable moments over the years, from Playboy playmate to devoted parent:
2004
Wilkinson, who was born and raised in San Diego, California, attended Hefner’s 78th birthday party as a full body paint model after the late Playboy founder came across a photo of Wilkinson.
“I was wearing nothing. I was wearing a couple of rhinestones – that was the craziest thing,” Wilkinson said during a previous interview with E!. “We had to stick these things one by one on my body. That’s when I first met Hef. I guess I caught his eye – I’m sure the rhinestones, I mean, you couldn’t miss me. That was the night that changed the rest of my life.”
Wilkinson went on to explain that Hefner asked her to be his girlfriend before the pair met in person.
“He asked me to be (his) girlfriend before meeting me,” he added. “A photo was sent to the Playboy A mansion for me to be hired as a body painted girl to work at the party. For some reason, it gave me this feeling of comfort. I was watching him and I was like, ‘He’s a good guy.'”
2005
Wilkinson and her colorful relationship with Hefner – which also included Madison and Marquardt – were documented in the hit reality TV show The Girls Next Door. The E! the series debuted in August 2005 and ran for five seasons, mainly following Madison, Marquardt and Wilkinson as they navigate the wild and wrong turns of life in the Playboy Mansion.
“At the end of the day, it’s a very awkward situation ’cause it’s not like we’re The Spice Girls,” Wilkinson said on Fox 5’s Good Day New York in 2015 and about her relationship with her costars. “We dated an 80-year-old man at the same time. It’s very awkward.”
The same year, Wilkinson appeared in an episode of Entouragetitled “Aquamansion.” In the scene, Wilkinson played an accomplice.
2008
By 2008, the first three Playboy models had ended their relationship with Hefner. During the final season of the reality show The Girls Next Doornew lovers Crystal Hefner (née Harris) and twins Kristina and Karissa Shannon joined the show.
2009
Wilkinson makes a brief cameo on an episode of How I Met Your Motherentitled “Benefits.” In the scene, Wilkinson appears on the cover of a magazine held by Marshall (Jason Segel), who have trouble using the bathroom at work.
That same year, Wilkinson married former NFL player Hank Baskett. The pair tied the knot at the Playboy Mansion, with Hefner in attendance, and later welcomed their son, Hank Baskett IV.
“We have already decided to name our son Hank Baskett IV,” Wilkinson wrote on her now-defunct blog, months before welcoming her son into the world. “Hank’s father and grandfather were named Hank, so it was very important to us to carry on the family tradition.
2010
Wilkinson debuts her memoir, Slide Homewhich revealed the highs and lows of her journey from the Playboy mansion to stay at mother’s home.
2011
Wilkinson appeared as a guest contestant on Season 12 of Dancing With The Stars alongside a professional dance partner Louis Van Amstel. The model was eventually eliminated in the seventh week of competition on May 3.
The same year, Wilkinson released her second book, Being Kendra: Cribs, Cocktails, and Getting Back Sexually. The so-called “total” memoir detailed her journey as a mother trying to maintain a long-distance relationship while fulfilling the demands of her television career.
2012
Wilkinson’s reality TV show, Kendra on Topdebuted on We TV, which followed the lives of her family of three at the time. The show ran between 2012 and 2017.
2014
The couple welcomed their baby girl Alijay Mary in May.
“I’ve been dreaming about little Hank holding his little sister for so long,” Wilkinson said People shortly after giving birth. “Little Hank had a huge smile and now knows he really is a big brother.”
Wilkinson and her ex-husband later hit the headlines after rumors emerged that he had been unfaithful while Wilkinson was eight months pregnant with their daughter.
“I messed up,” Baskett said a year later in an interview with him People. “I put myself in a bad position. And everything through me brought pain to this family. I didn’t take part in anything … It was like a bank robbery. You never know when you will freeze. I don’t know if it was a few seconds or 15 seconds, because all I was saying was, ‘Get out, get out, get out.’”
2018
Wilkinson officially filed for divorce from the former NFL player, citing irreconcilable differences and listing the separation date as January 1, 2018. The pair requested joint legal physical custody of their two children.
2019
Wilkinson and Baskett’s divorce was finalized.
“I went through a divorce, lost everything I knew, which was my TV show. I had a TV show every year until my divorce,” Wilkinson said during an August 22 appearance on the “On Display with Melissa Gorga” podcast. “Then my divorce happened and all of a sudden, now I’m left with no marriage, I’m left with no show, I had to move into a small house – I didn’t understand what was happening and true. suddenly I had to do some intense healing.”
2021
Wilkinson returned to reality TV with a new show, Kendra Sells Hollywood.
“Starting my show and starting filming was (also) the start of my new … journey,” the star exclusively said Us Weekly on November 9 while promoting his show. “Everything started immediately, including the decision to start dating. It just happened.”
He continued, “I needed to do some healing. When those cameras turned on — and I was ready to start my new career — all my confidence came back all at once. I don’t know what happened. It was not an ego. It was confidence.”
The show aired for two seasons.
2023
Wilkinson hit the headlines in September when she suffered a panic attack that sent her to hospital, Us confirmed at the time. In November of the same year, Wilkinson shared via Instagram that she had “finished treatment for my depression and anxiety.”
2025
Wilkinson had more than a few words to say to online naysayers who had disparaged the first Playboy the weight of the model.
“For those of you who hate my new weight, 40-year-old face, remember that I am finally happy, healthy, and at peace in life,” she wrote via Instagram in January. “Leave me alone and respect that I’m finally where I really want to be together.”
