Kendra Wilkinson
Getty Images (2)Former Playboy model and reality star Kendra Wilkinson is no stranger to the public eye.
The 39-year-old returned for the first time in 2004, when she attended late Playboy publisher Hugh Hefner78th birthday party. Immediately after the event, she was asked to switch to the icon Playboy mansion and began 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!'” recalls the California native. I’m a celebrity, get me out of here! in 2014. “I was living in this little apartment with this ugly-ass whore. I was praying for something to get me out of there. … I moved in and the weeks went by and I didn’t know sex was involved. I didn’t know anything about it PlayboyI had just finished high school.”
Wilkinson’s relationship with Hefner — along with his concurrent relationships with exes Playboy pattern Holly Madison AND Bridget Marquardt — was documented on the hit E! The reality series The girls next door. The reality series premiered in August 2005 and ran for five seasons. All three of their romantic relationships ended in 2008.
Since then, Wilkinson has appeared in several television shows including entourage, How I Met Your Mother AND Scary movie 4. She has also written two books and starred in her own reality TV show, Center at the topwhich documented her relationship with the former NFL wide receiver Hank Baskett. (The pair married in 2009 and welcomed two children together before divorcing in 2018.)
In 2025, Wilkinson made headlines after fiercely defending her weight, telling naysayers she was “not the girl I used to be”.
“Yes, I have gained weight. Yes, I’m getting old,” Wilkinson wrote on Instagram on Jan. 12. “Yes, I’m not the girl I used to be (playboy girl), but once in a while I feel good and mentally healthy.”
Read on for some of Wilkinson’s most memorable moments over the years, from Playboy pal 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 wasn’t wearing anything. I was wearing some rhinestones — it was the craziest thing,” Wilkinson said during a previous interview with Oh!. “We had to attach these things one by one to my body. That’s when I met Hefi for the first time. I think I caught his eye—I’m sure the diamonds, you mean, I couldn’t miss. That’s 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 even met in person.
“He asked me to be (his) girlfriend before he met me,” she added. “A photograph has been sent to Playboy Residence for me to be hired as a body painted girl to work at the party. For some reason, he gave me this feeling of comfort. I was just looking at him and I was like, ‘He’s a good guy.'”
2005
Wilkinson and her polyamorous relationship with Hefner — which also involved Madison and Marquardt — was documented on the hit reality TV show. The girls next door. Oh! The series debuted in August 2005 and ran for five seasons, mostly following Madison, Marquardt and Wilkinson as they navigated the wild ups and downs of life in Playboy Residence.
“At the end of the day, it’s a very difficult situation because 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 co-stars. “We met at the same time with an 80-year-old man. It’s very embarrassing.”
In the same year, Wilkinson appeared in an episode of entouragetitled “Aquamansion”. On stage, Wilkinson played a playmate.
2008
Until 2008, the three ex Playboy the models had ended their respective relationships with Hefner. During the last season of the reality show The girls next doornew girlfriends Crystal Hefner (née Harris) and the twins Christina and Karissa Shannon had joined the show.
2009
Wilkinson makes a cameo appearance in an episode of How I Met Your Motherentitled “Benefits”. On stage, Wilkinson appears on the cover of a magazine held by Marshall (Jason Segel), who struggles to use the bathroom at work.
That same year, Wilkinson married former NFL player Hank Baskett. The couple got married in 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 both named Hank, so it was very important to us to carry on the family tradition.
2010
Wilkinson debuted her memoir, Sliding at homewhich revealed both the highs and lows of her journey from Playboy residence to stay at home mom.
2011
Wilkinson appeared as a guest contestant on season 12 of Dancing With the Stars alongside the professional dance partner Louis Van Amstel. The model was finally eliminated in the seventh week of the competition on May 3.
In the same year, Wilkinson published her second book, Being Kendra: Cribs, cocktails, and a sexier return. The so-called tell-all memoir details her journey as a mother trying to maintain a long-distance relationship while juggling the demands of her television career.
2012
Wilkinson’s reality TV show, Center at the topdebuted on We TV, which followed the life of her family of three at the time. The show ran from 2012 to 2017.
2014
The couple welcomed their daughter Alijay Mary in May.
“I dreamed about little Hank holding his little sister for so long,” Wilkinson said The people shortly after birth. “Little Hank had a big smile and now I know he really is a big brother.”
Wilkinson and her ex-husband later hit the headlines after rumors surfaced 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 The people. “I put myself in a bad situation. And everything through me brought pain upon this family. I didn’t engage 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 physical legal custody of their two children.
2019
Wilkinson and Baskett’s divorce was finalized.
“I went through a divorce, I lost everything I knew, which was my TV show. I had a TV show every year until my divorce,” Wilkinson said during an Aug. 22 appearance on the “On Display with Melissa Gorga” podcast. show, I had to go to a little house – I didn’t understand what was going on and all of a sudden I had to do intensive healing.”
2021
Wilkinson returned to reality television with a new show, Kendra sells Hollywood.
“The start of my show and the start of filming was (also) the start of my … new journey,” the star exclusively said Us Weekly on Nov. 9 while promoting her show. “Everything started immediately, including the decision to start the meeting. It just happened.”
She continued, “I had to do some healing. When those cameras came on – and I was ready to start my new career – all my confidence came right back. I don’t know what happened. It wasn’t ego. It was faith.”
The show aired for two seasons.
2023
Wilkinson made headlines in September when she suffered a panic attack that sent her to hospital. us confirmed at the time. In November of that 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 the online naysayers who had scorned the former Playboy the weight of the model.
“For those of you who hate my new weight, 40-year-old face, please know that I am finally happy, healthy and at peace in life,” she wrote on Instagram in January. “Leave me alone and respect that I’m where I want to be when we’re finally together.”
