Kendra Wilkinson's New Chapter: Real Estate, Faith, and Moving On

Imagine that the person you were at 19 is how you’re perceived for the rest of your life. Welcome to Kendra Wilkinson’s world. At 40, the former reality star, who shot to stardom as one of Hugh Hefner's girlfriends, has now been working in real estate for more than five years — a stretch that already outlasts her time at the Playboy Mansion. Her life moved forward. The label stayed put. “I started my public life as a celebrity when I was 19,” Wilkinson tells Yahoo. “I was so young. My whole identity, for 20 years, was tied into that. I’m very grateful for what it brought me. TV was amazing. I had a great journey on camera. I love to entertain. But I didn’t realize how tightly my identity would stay tethered to that 19-year-old Playboy girl.” Advertisement Advertisement Advertisement She adds, “It was five years of my life. It shouldn’t be my entire identity.” Wilkinson didn’t reach out to me to complain about the persona that followed her from The Girls Next Door with Hugh Hefner to Kendra, Kendra on Top and Kendra Sells Hollywood. I contacted her after seeing paparazzi photos of her outside an open house for one of her listings — the kind of clickbait that tabloids post to feed trolls. To me, I saw a divorcée and working mom hustling to support her two kids, Hank, 16, and Alijah, 11, after well-documented mental health challenges. She was not dressed for the male gaze. She’s dressed for work. The photos didn’t bother Wilkinson. To her, they marked something else entirely. Advertisement Advertisement Advertisement “I would rather there be photos of me in a dumpy outfit putting up an open house sign than me in a short dress on a red carpet … being a celebrity for no reason,” she says. “It’s nice that people care to see me in my new world rather than pinning me down in my old life.” Wilkinson’s new life sees her working full-time with Ernie Carswell & Associates of Sotheby’s International Realty in Los Angeles, juggling clients across price points. She’s taking new clients, she says, and has learned to spot the difference between a serious buyer and someone who just wants to meet her. “There are a couple of reality shows that make it seem like it's all glitz and glam,” she says, referring to Selling Sunset and similar fare. “In reality, it's not. Real estate is not for the weak.” However, doing the hard work has given her a deeper sense of purpose than stardom ever did. Advertisement Advertisement Advertisement “Every deal that I close feels like proof of my evolution,” she says. “I did that without fame. I did it with my knowledge, my skills. I feel like a superhero.” Wilkinson said that while she was “once on top of the world” in the “high-energy, rock 'n' roll lifestyle” she was living — shows, books, parties and appearances around the globe — it was an empty existence in many ways. “I never felt successful,” she says. “I felt famous, but I never felt the actual feeling of success. Now, if I sell a $700,000 condo, I actually experience the feeling of success.” Wilkinson no longer views herself as a celebrity, but “a single mother … working her ass off to put food on the table” — a mindset that’s driving her professionally. Advertisement Advertisement Advertisement “I only get this opportunity one time to truly succeed on my own … in a business that doesn't involve sleeping with an 80-year-old, or selling my soul for a paycheck,” Wilkinson says. “Success beyond fame is a high that nothing else gives me.” For the record, Wilkinson’s work style is mindfully curated — in her words, “I purposely dress like shit just to piss people off.” She thinks that if she dresses “pretty, people are gonna think Playboy.” So she buttons all the way up — and purposefully covers her cleavage. “I would much rather be called ‘professional’ than ‘sexy’ nowadays,” she says. “‘Professional’ is a compliment that takes me beyond the clouds. ‘Sexy’ falls completely flat. It's part of my identity that I've completely let go of.” Advertisement Advertisement Advertisement Wilkinson has thought about removing her breast implants because they’re “not even close to who I am anymore,” she says. Maybe they never were, as she’s “always been this tomboy — besides my boobs,” she says. However, elective surgery to remove them is around $10,000, and “I'm not rich anymore,” she says. “I'd rather save that money for, like, a trip.” Wilkinson’s reinvention hasn’t come without cost. After her divorce from Hank Baskett, which was finalized in 2019, and pulling back from reality TV, Wilkinson faced identity whiplash. “I never knew life without cameras,” she says. “So when they shut off one day, my whole world turned upside down. I never prepared for that.” She agreed to be on Kendra Sells Hollywood, which aired from 2021 to 2023, to document her professional pivot, but she felt pressure to entertain the world again was a “toxic turn.” Advertisement Advertisement Advertisement Wilkinson’s mental health reached a breaking point, forcing her to seek treatment for depression and severe anxiety attacks in 2023, and rethink how she wanted to live. “I was left feeling extremely lonely and depressed,” she says. “I couldn't even breathe. I had no hope of the next day.” During that period, Wilkinson was on her knees “begging for mercy” — and found comfort in God. She began Bible study — with a group of older, nurturing women who became mom figures — which has given her structure and peace. “I've learned how to live a simpler, more peaceful life with God in it,” says Wilkinson, who doesn’t identify with a certain religion or attend church. “It’s completely changed my life for the better. … I've learned to put my mental health — and God — first.” Advertisement Advertisement Advertisement That doesn’t mean that Wilkinson doesn’t “still get out and I have a little fun.” As for dating, she doesn’t want a relationship to interfere with her professional ambition. However, friends with benefits are approved. While she’s on good terms with Baskett, she’s not sure she’ll ever remarry after their divorce: “Love and marriage … hurt me to my lowest of low.” What’s not OK are men she doesn’t know hopping into her DMs with expectations rooted in her past, which she finds unsettling rather than flattering. “I'm some dumpy ass realtor now — not this sex symbol. Why are all these men reaching out saying they love me?” she says with a laugh. “All these dudes do is think of me and Playboy, which is the complete opposite of who I am nowadays. It makes me so uncomfortable. These people haven't seen me evolve into this new woman I am.” The disconnect no longer feels defining — just exhausting. Advertisement Advertisement Advertisement “I remained almost hostage in this identity for 20 years,” Wilkinson says. “For the first time, I feel liberated. I get to just be who I really am.” That sense of freedom has reshaped how she sees fame altogether — especially now, as a mother. Wilkinson says her daughter has started talking about wanting to be famous — a thought that stops her cold. “That scares me,” Wilkinson says, ”because I know what that can bring. … It’s dangerous to be famous. There’s a lot of bloodshed, tears. It’s very lonely.” She encourages her kids to focus on school, sports, their instruments and eventually college — the kind of stability she didn’t have at their age. Advertisement Advertisement Advertisement These days, she sees her own story less as a cautionary tale about Playboy than about celebrity itself. “If you’re not careful,” she says, “Hollywood can really eat you up and spit you out. That's what I feel like it did to me.”