Kendra Wilkinson Through the Years: From Playboy Playmate to Mother

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Kendra Wilkinson Getty Images (2)

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

The 39-year-old first turned heads in 2004, when he appeared late playboy publisher Hugh HefnerIts 78th birthday party. Shortly after the event, he was asked to go to Iconic playboy Palace and Hefner began dating.

"He asked me to be one of his girlfriends, and to stay at the mansion, and I was like, 'Hell yeah, I'm here!'" the California resident recalled. I'm a celebrity, get me out of here! In 2014. “I was living in this little-ass apartment with this ugly-ass bitch. I was praying for something to get me out of there. … I moved in and weeks went by and I didn't know that sex was involved. I didn't know anything about it playboyI just passed high school."

Wilkinson's relationship with Hefner - including her simultaneous relationship with the former playboy model Holly Madison And Bridget Marquardt — The hit was recorded on E! The real 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.

Related: Kendra Wilkinson and Hank Baskett's Ups and Downs Through the Years

Kendra Wilkinson and Hank Baskett have been through a lot in their nearly decade of marriage — from cheating scandals and sex tape revelations to pregnancies and incest. The former couple, who share son Hank IV and daughter Aliza, have had more ups and downs than most since tying the knot in June 2009. (...)

Since then, Wilkinson has appeared in several television shows, including team, How I Met Your Mother And Scary Movie 4. He has also written two books and starred in his own reality television show, Center is at the topwhich documented his relationship with the former NFL wide receiver Hank Basket. (The couple married in 2009 and welcomed two children before divorcing in 2018.)

In 2025, Wilkinson fiercely followed the headlines Protect her weightTells Innocents that she's "not the girl I used to be."

“Yes, I have gained weight. Yes, I'm getting old,” Wilkinson wrote via Instagram on Jan. 12. "Yes, I'm not the girl I was before (the Playboy girl) but I feel good and mentally healthy for a long time."

From Playboy playmate to devoted parent, read on for some of Wilkinson's memorable moments throughout the years:

2004

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Steve Condles/Bauer-Griffin/GC Photo

Wilkinson, who was born and raised in San Diego, California, attended Hefner's 78th birthday party as a full-body paint model after seeing a photo of Playboy founder Wilkinson.

“I'm not wearing anything. I wore a couple of glasses - it was the craziest thing," Wilkinson said in a previous interview with E!. “We had to glue these things onto my body one by one. That's when I first met Hef. I guess I caught his eye — I'm sure Rystones, I mean, you can't miss me. That night 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 photo has been sent playboy I will be hired as a body painted girl to work at parties. 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

Her polyamorous relationship with Wilkinson and Hefner — which also included Madison and Marquardt — was documented on the hit reality television show. The Girls Next Door. E! The series debuted in August 2005 and ran for five seasons, initially following Madison, Marquardt and Wilkinson as they navigated life's wild ups and downs. playboy Palace.

Related: Kendra Wilkinson 'respects' former players who spoke out against Hugh Hefner

Getty Images; Michael Kovac/FilmMagic Kendra Wilkinson shares her support for fellow playmates who spoke out about the late Hugh Hefner. Wilkinson, 38, "honored" her fellow The Girls Next Door alums Holly Madison and Bridget Marquardt in an interview with People published Wednesday, Jan. 17. "The timing is funny because it really does (...)

"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 about her relationship with her fellow 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 teamThe title is "Aquamansion." In the scene, Wilkinson plays a playmate.

2008

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Michael Locisano/FilmMagic

By 2008, all three ex playboy The models ended their respective relationships with Hefner. During the final season of the reality show The Girls Next Doornew girlfriend Crystal Hefner (née Harris) and twins Christina and Karissa Shannon Joined the show.

2009

Wilkinson makes a brief cameo in one episode How I Met Your MotherTitle "Benefits." In the scene, Wilkinson appears on the cover of a magazine held by Marshall (Jason Segel), who struggle to use the bathroom at work.

That same year, Wilkinson married former NFL player Hank Baskett. The couple tied the knot playboy Mansion, attended with Hefner 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 his grandfather were both named Hank, so it was very important to us to keep the family tradition going.

2010

Wilkinson debuted his memoirs, Sliding homefrom which revealed both the highs and lows of his journey playboy Palace mom to stay at home.

2011

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Wilkinson appeared as a guest contestant in season 12 Dancing with the Stars Along with a professional dance partner Louis van Amstel. The model was finally eliminated on May 3 in the seventh week of the competition.

Related: Kendra Wilkinson Teases 'Woman-to-Woman' Convo With Crystal Hefner

Get ready to do some real talking. Kendra Wilkinson has revealed that she and her ex Hugh Hefner's widow, Crystal Hefner, will share an emotional conversation on Season 2 of Kendra Sells Hollywood. "We had eye to eye," the former Playboy playmate, 37, told Us Weekly exclusively while promoting the new season of her Max Reality (...)

The same year, Wilkinson published his second book, Being Center: Cribs, Cocktails and Getting My Sexy Back. 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 television show, Center is at the topWee debuted on TV, which followed the life of her family of three. The show ran from 2012 to 2017.

2014

The couple welcomed their baby girl Alijoy Marie in May.

“I was dreaming that little Hank was holding his little sister for so long,” Wilkinson said people Immediately 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 when rumors surfaced that he had been unfaithful while Wilkinson was eight months pregnant with their daughter.

"I messed up," Baskett said in an interview a year later people. “I put myself in a bad situation. And everything through me has hurt this family. I'm not involved in anything... it's like a bank robbery. You never know when you'll 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

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

2019

Wilkinson and Baskett's divorce was final.

“I went through a divorce, I lost what 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 the Show With Melissa Gorga” podcast. "Then I got divorced and all of a sudden, now I'm not married, I don't have a show, I had to move into a small house — I didn't understand what was going on and all of a sudden I had to do some intense healing."

2021

Wilkinson returns to reality television with a new show, The center sells Hollywood.

"The start of my show and the start of filming was (also) the start of my new ... journey," the star exclusively said. our weekly November 9 while promoting his show. “Everything started at once, including the decision to start dating. It just kind of happened."

Related: Kendra Wilkinson went to the emergency room after having a panic attack

Rodin Eckenroth/Getty Images Kendra Wilkinson went to a local hospital's emergency room after having a panic attack, Us Weekly can confirm. A rep for Wilkinson, 38, told Us that the former Playboy model was not admitted to the hospital on Wednesday, September 6 due to fears for her health. "He's going home soon," added the spokesperson (...)

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 back at once. I don't know what happened. It wasn't ego. It was confidence."

The show aired for two seasons.

2023

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Paul Archuleta/Getty Images

Wilkinson made headlines in September when she suffered a panic attack that sent her to hospital, our confirmed in 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 naysayers online who insulted 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 with life," she wrote via Instagram in January. "Leave me alone and respect that I'm where I want to be finally together."



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