Kendra Wilkinson Through the Years: From Playboy Playmate to Mom

Former Playboy model and reality star Kendra Wilkinson no stranger to society.

The 39-year-old first turned heads in 2004 when she visited late Playboy the publisher Hugh Hefner78th birthday party. Shortly after the event, she was asked to switch to 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, I'm here!'” the California native recalled. I'm a celebrity, get me out of here! in 2014. “I live in this tiny apartment with this ugly dog. I begged for anything to get me out of there. … I moved in and weeks went by and I didn't know sex was involved. I didn't know anything about Playboyi just finished high school.

Wilkinson's relationship with Hefner – along with his concurrent relationship with his ex Playboy models Holly Madison and Bridget Marquardt — was documented on 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 in a number of television shows including Suite, How I Met Your Mother and Scary movie 4. She has also written two books and starred in her own reality television show, Kendra abovewhich documented her relationship with the former NFL wide receiver Hank Baskett. (The couple married in 2009 and had two children together before divorcing in 2018.)

In 2025, Wilkinson made headlines after going on a rampage defending your weightclaiming that she is not the girl I used to be.

“Yes, I've gained weight. Yes, I'm getting older,” Wilkinson wrote via Instagram on Jan. 12. “Yes, I'm not the girl I used to be (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 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 Wilkinson's picture.

“I wasn't wearing anything. I was wearing a couple of rhinestones — that was the craziest thing,” Wilkinson said in a previous interview with E!. “We had to stick these things one by one on my body. That's when I met Hef for the first time. I think 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 me life.

Wilkinson explained that Hefner asked her to be his girlfriend before the couple actually met.

“He asked me to be (his) girlfriend before meeting me,” she added. “The image was sent to Playboy Mansion to hire me as a body painted girl to work at a party. For some reason he gave me this feeling of comfort. I just watched him and thought, “He's a good guy.”

2005 year

Wilkinson and her polyamorous relationship with Hefner, which also featured Madison and Marquardt, were documented on the hit reality television show. The Girls Next Door. E! the series debuted in August 2005 and ran for five seasons, mostly following Madison, Marquardt and Wilkinson as they navigated the ups and downs of wild life Playboy A detached house.

“At the end of the day, it's a very awkward 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 an 80-year-old man at the same time. It is very inconvenient. “

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

2008

Until 2008, all three former Playboy models had ended their relationship with Hefner. During the final season of the reality show The Girls Next Doornew girlfriends Crystal Hefner (born Harris) and twins Christina and Carissa Shannon had joined the show.

2009

Wilkinson makes a cameo for the episode How I Met Your Motherentitled “Benefits”. In this scene, Wilkinson appears on the cover of a magazine held by Marshall (Jason Segel), who finds it difficult to use the bathroom at work.

That same year, Wilkinson married former NFL player Hank Baskett. The couple tied the knot at Playboy Mansion, which Hefner attended 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 several months before welcoming her son into the world. “Hank's dad and his grandfather were named Hank, so it was very important to us to carry on the family tradition.

2010

Wilkinson made her memoir debut, Skating at homewhich revealed both the highs and lows of her journey from Playboy a mansion for a stay-at-home mom.

2011

Wilkinson made a guest appearance in season 12 Dancing with the stars with a professional dance partner Louis Van Amstel. The model was eventually 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 sexy comebacks. The so-called tell-all memoir detailed her journey as a mom trying to maintain a long-distance relationship while juggling the demands of her television career.

2012 year

Wilkinson's reality TV show, Kendra abovedebuted on We TV, which followed the life of her then family of three. The show ran from 2012 to 2017.

2014 year

The couple welcomed their daughter, Aliyah 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 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 caused pain to this family. I wasn't involved in anything… It was like a bank robbery. You never know when you're going to freeze. I don't know if it was a couple of seconds or 15 seconds because all I said was, 'Get out, get out, get out.'”

2018

Wilkinson officially filed for divorce from the former NFL player, citing irreconcilable differences and setting the divorce date as January 1, 2018. The couple requested joint physical custody of the two children.

2019 year

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 Aug. 22 during an appearance on the “On Display with Melissa Gorga” podcast. “Then my divorce happened and all of a sudden, now I'm out of a marriage, I'm out of a show, I had to move into a small house — I didn't understand what was going on and everything. All of a sudden I had to do intense healing.

The year 2021

Wilkinson returned to reality TV with a new show, Kendra is selling Hollywood.

“The start of my show and the start of filming was (also) the start of my new… journey,” the star shared exclusively Us Weekly on November 9, promoting his show. “Everything started right away, including the decision to start dating. It just happened. “

She continued, “I needed to do some healing. When those cameras came on and I was ready to start my new career, my confidence came right back. I don't know what happened. It wasn't selfishness. It was confidence.”

The show ran for two seasons.

The year 2023

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

The year 2025

Wilkinson had more than a few words to say to online detractors who had disparaged the former Playboy model weight.

“For those of you who hate my new weight, 40-year-old face, please know that I am happy, healthy and finally at peace,” she wrote on Instagram in January. “Leave me alone and respect that I'm where I really want to be when we're all together.”