Kendra Wilkinson through the years: from Playboy girlfriend to mom

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

The 39-year-old first attracted attention in 2004 when she was late Playboy the publisher Hugh Hefner78th birthday. Shortly after the event, she was asked to move to the cult Playboy mansion and began dating Hefner.

“Hef asked me to be one of his girlfriends and live in the mansion, and I was like, ‘Fuck, I’m here!'” the California native recalled. I’m a celebrity, get me out of here! in 2014. “I lived in this little apartment with this ugly bitch. I prayed for something to save me from there. …I moved and weeks went by and I didn’t know it was sex. I knew nothing 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 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 TV shows, including Entourage, How I Met Your Mother and Scary movie 4. She has also written two books and starred in her own reality show, Kendra is on topwhich 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 hit the headlines after a furious protecting his weighttelling naysayers that she is “not the girl she used to be”.

“Yes, I gained weight. “Yes, I’m getting old,” Wilkinson wrote via Instagram on Jan. 12. “Yes, I’m not the girl I used to be (playboy girl), but for the first time in a long time I feel good and mentally healthy.”

From Playboy girlfriend to devoted parent, read some of Wilkinson’s most memorable moments throughout the years:

2004 year

Wilkinson, who was born and raised in San Diego, California, attended Hefner’s 78th birthday party as a model with body paint after the Playboy founder came across Wilkinson’s photo.

“I wasn’t wearing anything. I wore a pair of rhinestones — it was the craziest thing,” Wilkinson said during a previous interview with E!. “We had to glue these things one by one to my body. That was when I first met Hef. I guess I caught his eye – I’m sure rhinestones, I mean, you couldn’t have missed 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 couple ever met in person.

“He asked me to be (his) girlfriend before he met me,” she added. “The photo was sent to Playboy Mansion for me to be hired as a body painted girl to work the party. Somehow he made me feel comfortable. I just watched him and thought, “He’s a good guy.”

2005 year

Wilkinson and her polyamorous relationship with Hefner, which also included Madison and Marquardt, were documented on the hit reality show. Girls next door. E! The series debuted in August 2005 and ran for five seasons, mainly following Madison, Marquardt and Wilkinson as they experience the wild ups and downs of life on Playboy Mansion.

“At the end of the day, it’s a very embarrassing situation because we’re not the Spice Girls,” Wilkinson said on Fox 5’s Good Afternoon New York in 2015 and about her relationship with the other cast members. “We met an 80-year-old man at the same time. It’s very embarrassing.”

Wilkinson appeared in an episode that same year Entouragecalled Aquamancy. In the scene, Wilkinson played a playmate.

2008 year

By 2008, all three were former Playboy models ended their relationship with Hefner. In the last season of the reality show Girls next doornew girlfriends Crystal Hefner (née Harris) and twins Christina and Carissa Shannon joined the show.

2009 year

Wilkinson makes a brief cameo in the episode How I Met Your Motherentitled “Benefits”. In the scene, Wilkinson appears on the cover of a magazine held by Marshall (Jason Segel), who has difficulty using the toilet at work.

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

2010 year

Wilkinson debuted her memoir, Sliding into the housewhich revealed both the highs and lows of her journey from Playboy a mansion for a stay-at-home mom.

2011 year

Wilkinson made a guest appearance in season 12 Dancing with the stars along with a 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: Cheat Sheets, Cocktails, and Reclaiming My Sexuality. 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 year

Wilkinson’s reality show, Kendra is on topdebuted on We TV, which followed the lives of her then-family of three. The show ran from 2012 to 2017.

2014 year

In May, the couple had a baby girl, Aliya Mary.

“I’ve been dreaming about little Hank holding his little sister for so long,” Wilkinson said. People soon after giving birth. “Little Hank had a huge smile and now he knows he really is a big 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 was wrong,” Baskett said a year later in an interview People. “I put myself in a bad situation. And everything through me brought pain to this family. I didn’t do anything… It was like robbing a bank. You never know when you will freeze. I don’t know if it was a couple of seconds or 15 seconds because all I was saying was, “Go away, go away, go away.”

2018 year

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

2019 year

Wilkinson and Baskett’s divorce was finalized.

“I went through a divorce, I lost everything I knew, and this 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 my divorce happened, and all of a sudden I was single, I was single, I had to move into a small house — I didn’t understand what was going on, and all of a sudden I had to go through intensive treatment.”

2021 year

Wilkinson is back on the reality show with a new show, Kendra sells Hollywood.

“Starting my show and starting filming was (also) the start of my new … journey,” the star said exclusively Us Weekly Nov. 9 while promoting his show. “Everything started at once, including the decision to start dating. It just happened.”

She continued: “I needed to heal. When those cameras rolled on – and I was ready to start my new career – all my confidence just came right back. I don’t know what happened. It wasn’t ego. It was confidence.”

The show ran for two seasons.

2023 year

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 year

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

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