18-Year-Old Kendra Wilkinson Dated 78 YO Hugh Hefner, Is Looking For Love On Dating Apps Now
Kendra Wilkinson has an eccentric love life, from living with 60-year-old Hugh Hefner to being ignored by a dating app.
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Add BollywoodShaadis on GoogleKendra Wilkinson, an American television personality, model, and real estate agent, has been making headlines ever since she opened up about her career setback. In July 2026, she posted a tearful video on Instagram admitting she was "struggling" after being fired by a real estate client. She opened up about the hardships she has been facing since transitioning from reality TV to real estate work. Kendra shared the emotional toll and pressure of building a business and working in the competitive Los Angeles market.
Recently, things got even tougher for her as she was fired by a luxury real estate client. Amid her struggles, her age-gap relationship with Hugh Hefner has come under the spotlight.
Kendra Wilkinson was involved in a physical relationship with 60-years-older Hugh Hefner
Kendra Wilkinson first gained popularity due to her appearance in the E! reality series The Girls Next Door. In the show, she appeared as one of the three girlfriends of now-deceased businessman Hugh Hefner. She was 18 when she began her relationship with Hugh, who was 78 years old at that time and was also dating models Holly Madison and Bridget Marquardt simultaneously. Kendra moved into the Playboy Mansion in 2004, following which she starred with Hugh in The Girls Next Door.
Kendra stated that she had just graduated high school and moved into the mansion because she wanted to party and experience the glam life. She shared that she didn't realize that intimacy would also be part of the arrangement. Although a little taken aback at first, she eventually got into a physical relationship with Hugh a few weeks after moving in with him.
Kendra, who has not been very lucky in love, always spoke highly of the entrepreneur. In the Skinny Confidential podcast, she said a simple word like dating couldn't describe their relationship, as it was one of deep friendship. As per Kendra, although their union was primarily for sexual purposes, they developed a good bond. She called Hugh Hefner "a very nice person" and mentioned:
"It was a heavenly experience for me. Like there couldn't have been a better experience...I have bad experiences when it comes to the business side of things...Not Heff. Heff was a very awesome guy to me. He was a generous, nice person. A very nice person. I don't see him in any other way."
Kendra called him a "great friend" and said that they loved each other but not in the conventional way. Their bond was difficult for outsiders to understand, as during their relationship, he had two other young women living with him while she was dating other men. She stated:
"He was a great friend to me, we loved each other in a different way. I was not dating Hugh Hefner. I had like boyfriends. I had so many boyfriends. That's why I was ready for marriage at that time because I went through my real dating process while I was at the mansion. Never really got out, but I had my fun."
Kendra Wilkinson's life after ending her live-in setup with Hugh Hefner
Kendra Wilkinson moved out of Hugh Hefner's mansion when she fell in love with and decided to get hitched to former NFL wide receiver Hank Baskett. The couple got married in June 2009 and, after nine years, filed for divorce in 2018, which got finalized in 2019. They share two children, Hank Baskett IV and Alijah Mary Baskett, and are focused on co-parenting.
Since Kendra's split, she has dated some people casually and had occasional sexual encounters with a few, but none of them emerged as long-term partners. She revealed she was looking for something serious, but it seems like she hasn't had any luck yet. She also tried looking for love on the dating app Raya, but she has been on the waitlist of the celebrity-preferred platform for four years. Kendra jokingly told PEOPLE:
"I swear to God, and they will not let me in...Dating world, Kendra is not coming in. So the universe is basically saying, 'We're not ready for you. Dating world, Kendra is not coming in. You better, you better wait an extra five years.'"
What are your thoughts on Kendra Wilkinson's eccentric dating history? Let us know.
Photos courtesy: Elayne Lodge/Playboy Enterprises
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