Kendra Wilkinson Through the Years: From Playboy Playmate to Mom

Kendra Wilkinson
Getty Images(2)former playboy model and reality star Kendra Wilkinson Not unfamiliar to the public.
The 39-year-old first attracted attention in 2004 when she showed up late to class playboy Publisher Hugh Hefner78th birthday party. Shortly after the event, she was asked to move into the iconic playboy mansion and began dating Hefner.
“Hef invited me to be one of his girlfriends and live in the mansion, and I was like, ‘Oh my God, I’m here!'” the California native recalled. I’m a Celebrity, Get Me Out of Here! 2014. I prayed that something would get me out of there. …I moved in and a few weeks went by and I had no idea sex was involved. i know nothing playboyI just graduated from high school.
Wilkinson’s relationship with Hefner—and his concurrent relationship with his ex playboy model Holly Madison and Bridget Marquardt — documented in the hit reality series E! girl next door. The reality show premiered in August 2005 and ran for five seasons. All three of their relationships ended in 2008.
Since then, Wilkinson has appeared in several television shows, including Entourage, how I Met Your Mother and horror movie 4. She has also written two books and starred in her own reality TV show, kendra on topchronicling her relationship with the former NFL wide receiver Hank Baskett. (The two married in 2009, had two children, and divorced in 2018.)
In 2025, Wilkinson made headlines for fiercely defending her weight, telling opponents she was “not the same girl anymore.”
“Yes, I’ve gained weight. Yes, I’m getting older,” Wilkinson wrote on Instagram on January 12. “Yes, I’m not the girl I used to be (the Playboy girl), but I feel good and mentally healthy for a long time.
Read about 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 body-painted model after the late Playboy founder saw a photo of Wilkinson.
“I wasn’t wearing anything. I was wearing a couple of rhinestones – it was the craziest thing,” Wilkinson said in a previous interview. Well!. “We had to glue these things on my body one by one. That was when I first met Hef. I think I caught his attention – I’m sure Rhinestone, I mean, you don’t I will be missed. That night changed the rest of my life.
Wilkinson went on to explain that Hefner asked her to be his girlfriend before the two actually met.
“He asked me to be [his] My girlfriend before I met her,” she added. “A photo has been sent to playboy The mansion got me hired as a body paint girl to work at parties. For some reason, he gave me this feeling of comfort. I just looked at him and thought, ‘He’s a good guy.
2005
Wilkinson and her polyamorous relationship with Hefner, which also included Madison and Marquardt, were documented on the hit reality TV show girl next door. E! The show premiered in August 2005 and ran for five seasons, focusing on the ups and downs of Madison, Marquardt and Wilkinson’s school lives. playboy building.
“At the end of the day, it’s a very awkward situation because we’re not like the Spice Girls,” Wilkinson said of her relationship with her co-stars on Fox 5’s Good Day New York in 2015. “We were dating an 80-year-old man at the same time. It was very awkward.
In the same year, Wilkinson appeared in Entouragetitled “Aquaman.” In this scene, Wilkinson plays a playmate.
2008

By 2008, the top three playboy Models ended relationships with Hefner. during the final season of the reality show girl next doornew girlfriend Christopher Hefner (née Harris) and twins Christina Shannon and Carissa Shannon has joined the show.
2009
Wilkinson made a brief cameo in one episode how I Met Your Mothertitled “Benefits.” In the scene, Wilkinson appears on the cover of a magazine held by Marshall (Jason Segel), it is difficult to use the bathroom at work.
That same year, Wilkinson married former NFL player Hank Baskett. The two tied the knot at the wedding playboy Hefner attended the mansion and later welcomed their son, Hank Baskett IV.
“We have decided to name our son Hank Baskett IV,” Wilkinson wrote on her now-defunct blog a few months before welcoming her son into the world. “Hank’s father and grandfather were both named Hank, so continuing the family tradition is very important to us.
2010
Wilkinson publishes her memoirs for the first time, slide into homerevealing her origins from playboy Homestead for stay-at-home mom.
2011

Wilkinson appeared as a guest contestant in season 12 dance with the stars with a professional dance partner Louis van Amstel. The model was ultimately eliminated in the seventh week of competition on May 3.
That same year, Wilkinson published her second book, Being Kendra: Cribs, Cocktails, and Regaining Sexiness. The so-called “tell-all” memoir details her journey as a mother trying to maintain a long-distance relationship while meeting the demands of a television career.
2012
wilkinson’s reality tv show, kendra on topdebuted on We TV, telling the story of her life as a family of three at that time. The play lasted from 2012 to 2017.
2014
The two welcomed their baby girl, Alijay Mary, in May.
“I always dreamed of little Hank holding his sister,” Wilkinson told people Soon after giving birth. “Little Hank has a big smile and now he knows he really is a big brother.”
Wilkinson and her ex-husband later made headlines amid rumors that Wilkinson had been unfaithful to him while she 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. Everything I did caused pain for this family. I did nothing… It was like robbing a bank. You never know when you’re going to get frozen. I don’t know if it was a few seconds or 15 seconds, because I just said, ‘Get out, get out, get out.’
2018

Wilkinson officially filed for divorce from the former NFL player, citing irreconcilable differences, and set the date of separation as January 1, 2018.
2019
Wilkinson and Baskett’s divorce case finalized.
“I went through a divorce and lost everything I knew, which was my TV show. Before the divorce, I was on a TV show every year. “Then I got divorced, and all of a sudden, I didn’t have a marriage, no I had to move into a small house – I didn’t understand what was going on and everything went to hell. “All of a sudden I had to go through some intense therapy.
2021
Wilkinson returns to reality TV with new show, kendra sells hollywood.
“The beginning of my acting and 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 therapy. When those cameras came on – and I was ready to start my new career – all my confidence came back at once. I didn’t know what was going on. This wasn’t ego. This was It’s confidence.
The show ran for two seasons.
2023

Wilkinson made headlines in September when she experienced a panic attack and was rushed to hospital. us Confirmed at the time. In November of that year, Wilkinson shared via Instagram that she had “completed treatment for depression and anxiety.”
2025
Wilkinson has plenty to say to online naysayers who disparage the former playboy The weight of the model.
“For those of you who hate my new 40-year-old weight, please know that I am happy, healthy, and finally at peace with my life,” she wrote via Instagram in January. “Leave me alone and respect me because I really want to be together right now.”