Kendra Wilkinson Through the Ages: From Playboy Playmate to Mom

Former Playboy model and reality star Kendra Wilkinson he is not a stranger in the public eye.

The 39-year-old woman first turned heads in 2004, when she went late Playboy the publisher Hugh Hefner78th birthday party. Soon after the ceremony, he was asked to move on to the hall of fame Playboy and started dating Hefner.

“Hef asked me to be one of his girlfriends, and to live in a mansion and I was like, ‘Hell yeah, I’m here!'” the California native recalled. I’m A Celebrity, Get Me Out Of Here! in 2014. “I used to live in this little donkey flat with this wicked woman. I was praying for anything to get me out of there. … I stayed for weeks and had no idea that sex was involved. I didn’t know anything PlayboyI had just finished high school.”

Wilkinson’s relationship with Hefner – and his simultaneous relationship with his predecessors Playboy models Holly Madison again Bridget Marquardt – was written on the hit E! The original series Girls Next. The original 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 numerous television shows, including The circle, How I Met Your Mother again Horror Movie 4. He has also written two books and starred in his own reality television show, Kendra upwhich documented his relationship with a former NFL wide receiver Hank Baskett. (The couple married in 2009 and welcomed two children before divorcing in 2018.)

In 2025, Wilkinson made headlines after fiercely defending her weight, telling naysayers that she “isn’t the girl I used to be.”

“Yes, I have gained weight. Yes, I’m getting old,” Wilkinson wrote on Instagram on January 12. “Yes, I’m not the playboy girl I used to be (playboy girl) but for once in a long time I feel good and sane.”

Read on for some of Wilkinson’s most memorable moments over the years, from Playboy co-star 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 Wilkinson’s photo.

“I wasn’t wearing anything. I was wearing a few rhinestones – it was the craziest thing,” Wilkinson said in a previous interview with. E!. “We had to attach these things one by one to my body. It was then that I met Hef for the first time. I think I caught her eye – I’m sure the rhinestones, I mean, you couldn’t miss me. It was that night that changed my whole life.”

Wilkinson went on to explain that Hefner asked her to be his girlfriend before the two met in person.

“He asked me to be [his] girlfriend before meeting me,” he added. “A picture was sent to Playboy A mansion so I can be hired as a body paint girl to work at a party. For some reason, he gave me this comforting feeling. I just looked at him and said, ‘He’s a good man.’

2005

Wilkinson and her polyamorous relationship with Hefner – which also involved Madison and Marquardt – were filmed in a reality television series. Girls Next. IE! The series premiered in August 2005 and ran for five seasons, primarily following Madison, Marquardt and Wilkinson as they navigate the difficult times of life in Playboy A mansion.

“At the end of the day, it’s a really bad situation because it’s not like we’re the Spice Girls,” Wilkinson said on Fox 5’s Good Day New York in 2015 about her relationship with the other passengers. “We dated an 80-year-old man at the same time. It’s very strange.”

That same year, Wilkinson appeared in an episode of The circletitled “Aquamansion.” In the incident, Wilkinson played with his partner.

2008

In 2008, all three are former Playboy models had ended their relationship with Hefner. During the last season of the reality show Girls Nextnew girlfriends Crystal Hefner (née Harris) and twins Kristina and Karissa Shannon had joined the show.

2009

Wilkinson makes a brief cameo in an episode of How I Met Your Motherentitled “Benefits.” In the scene, Wilkinson appears on the cover of a magazine owned by Marshall (Jason Segel), who struggles to use the bathroom at work.

That same year, Wilkinson married former NFL player Hank Baskett. The two tied the knot Playboy Mansion, with Hefner present, and later welcomed their son, Hank Baskett IV.

“We have already decided to name our son Hank Baskett IV,” Wilkinson wrote on her late 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 released his first memoir, Skiing Goes Homewhich reveals both the highs and lows of his journey from Playboy a house for a housewife.

2011

Wilkinson appeared as a guest contestant on Season 12’s Dancing with the Stars alongside a professional dance partner Louis Van Amstel. The model was finally released in the seventh week of the competition on May 3.

That same year, Wilkinson released his second book, Being Kendra: Cribs, Cocktails, and Reclaiming My Sexy. The tell-all 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 television show, Kendra at the topwhich premiered on We TV, which followed the lives of his then three-member family. The program ran from 2012 to 2017.

2014

The couple welcomed their baby girl Alijay Mary in May.

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

Wilkinson and her ex-husband later hit the headlines after rumors surfaced that he had been unfaithful when Wilkinson was eight months pregnant with their daughter.

“I messed up,” Baskett said a year later in an interview People. “I put myself in a bad situation. And everything about me brought pain to this family. I wasn’t involved 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 has officially filed for divorce from the former NFL player, citing irreconcilable differences and listing the separation date as January 1, 2018. The two have requested joint physical 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 television 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, suddenly, now I’m single, I’m left with a show, I had to go and live in a small house — I didn’t understand what was happening and all of a sudden I had to do a lot of healing.”

2021

Wilkinson is back on reality TV with a new show, Kendra Sells Hollywood.

“The beginning of my program and the beginning of recording was there [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.”

He continued, “I needed to heal. When those cameras rolled on – and I was ready to start my new job – all my confidence came back all at once. I don’t know what happened. It wasn’t ego. It was confidence.”

The show ran for two seasons.

2023

Wilkinson made headlines in September when she suffered a panic attack that sent her to hospital, Us confirmed at that time. In November of the same year, Wilkinson shared on Instagram that she had “completed treatment for my depression and anxiety.”

2025

Wilkinson had more than a few words to say to the naysayers on the internet who scorned the original Playboy model weight.

“For those of you who hate my new weight, my 40 year old face please know that I am finally happy, healthy, and at peace in life,” she wrote on Instagram in January. “Let go and respect that I am where I want to be in the end.”