Kendra Wilkinson Through the Years: From Playboy Playmate to Full-Time Mom

Former Playboy model and reality star Kendra Wilkinson is no stranger to the public eye.

The 39-year-old first turned heads in 2004, when she attended late Playboy publisher Hugh Hefner’s 78th 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 on I’m a Celebrity, Get Me Out of Here! 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.”

Wilkinson’s relationship with Hefner — along with his simultaneous relationships with former Playboy models Holly Madison and Bridget Marquardt — was 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 of their romantic relationships ended in 2008.

Since then, Wilkinson has appeared on several television shows, including Entourage, How I Met Your Mother and Scary Movie 4. She has also authored two books and starred in her own reality television show, Kendra on Top, which documented her relationship with former NFL wide receiver Hank Baskett. (The pair married in 2009 and welcomed two children before divorcing in 2018.)

In 2025, Wilkinson made headlines after fiercely defending her weight, telling naysayers she’s “not that girl I was before.”

“Yes, I’ve gained weight. Yes, I’m aging,” Wilkinson wrote via Instagram on January 12. “Yes, I’m not that girl I was before (playboy girl) but for once in a long time I feel good and mentally healthy.”

Read on for some of Wilkinson’s most memorable moments throughout 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 picture of Wilkinson.

“I was wearing nothing. I was wearing a couple of rhinestones – it was the craziest thing,” Wilkinson said during a previous interview with E!. “We had to glue these things one by one onto 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’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 actually met in person.

“He asked me to be [his] girlfriend before meeting me,” she added. “A picture was sent to the Playboy Mansion 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 watching him and I was like, ‘He’s a good guy.’”

2005

Wilkinson and her polyamorous relationship with Hefner — which also included Madison and Marquardt — was documented in the hit reality television show The Girls Next Door. The E! series debuted in August 2005 and ran for five seasons, primarily following Madison, Marquardt and Wilkinson as they navigated the wild ups and downs of life at 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 of her relationship with her fellow costars. “We dated an 80-year-old man at the same time. It’s very awkward.”

That same year, Wilkinson appeared in an episode of Entourage, titled “Aquamansion.” In the scene, Wilkinson played a playmate.

2008

By 2008, all three former Playboy models had ended their respective relationships with Hefner. During the final season of the reality show The Girls Next Door, new girlfriends Crystal Hefner (née Harris) and twins Kristina and Karissa Shannon had joined the show.

2009

Wilkinson makes a brief cameo on an episode of How I Met Your Mother, titled “Benefits.” In the scene, 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 pair tied the knot at the Playboy Mansion, with Hefner in attendance, and later welcomed their son, Hank Baskett IV.

“We’ve already decided to name our son Hank Baskett IV,” Wilkinson wrote on her now defunct blog months before welcoming her son to the world. “Hank’s dad and his grandfather were both named Hank, so it was very important to us to carry on the family tradition.

2010

Wilkinson debuted her memoir, Sliding Into Home, which revealed both the highs and lows of her journey from the Playboy mansion to stay-at-home mom.

2011

Wilkinson appeared as a guest contestant on Season 12 of Dancing With the Stars alongside professional dancing partner Louis Van Amstel. The model was ultimately eliminated in the seventh week of competition on May 3.

That same year, Wilkinson released her second book, Being Kendra: Cribs, Cocktails, and Getting My Sexy Back. The so-called “tell-all” memoir detailed her journey as a mom trying to sustain a long-distance relationship while fulfilling the demands of her television career.

2012

Wilkinson’s reality television show, Kendra on Top, debuted on We TV, which followed the lives of her at-the-time family of three. The show ran from 2012 to 2017.

2014

The pair welcomed their baby girl Alijay Mary in May.

“I’ve been dreaming about little Hank holding his little sister for so long,” Wilkinson told People shortly after giving birth. “Little Hank had a huge smile and he now knows he really is a big brother.”

Wilkinson and her ex husband later made 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 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’ll freeze. I don’t know if it was a couple of 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 date of separation 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 little house — I didn’t understand what was going on and all of a sudden I had to do some intense 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 told Us Weekly on November 9 while promoting her show. “Everything just started all at once, including the decision to start dating. It just kinda happened.”

She continued, “I needed to do some healing. When those cameras turned on — and I was ready to start my new career — all my confidence just came back all at once. I don’t know what happened. It wasn’t ego. It was confidence.”

The show aired for two seasons.

2023

Wilkinson made headlines in September when she experienced a panic attack that sent her to the hospital, Us confirmed at the time. In November that 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 naysayers online who had disparaged the former Playboy model’s weight.

“For those of you hating on my new weight, 40 yr old face please know that I’m happy, healthy, and at a peace in life finally,” she wrote via Instagram in January. “Leave me alone and respect that I’m where I actually want to be finally all together.”