‘Kendra Sells Hollywood’ Season 2 Premiere Date Announced

Kendra Wilkinson is back for another season of Kendra Sells Hollywood, and this time, the former Girls Next Door star is looking to put her Playboy past behind her and find success in the high-stakes world of luxury real estate. Season 2 of Kendra Sells Hollywood returns on May 26, having found a new home on HBO Max.

It won’t be easy for Wilkinson to make her six-figure quote as she takes on the Los Angeles real estate market, and it’s only made harder with her past looming over her with both her clients and her fellow agents at Douglas Elliman. In a trailer for the upcoming season, the 37-year-old sits down with a client who asks, “I’ve known you as a Playmate. How can I really put my confidence in you?” Wilkinson then gets emotional telling a friend, “I’m some Playboy girl forever, desperate for fame, wanting to sell a house. That’s the story.”

The mother of two also gets a call from late Playboy founder Hugh Hefner’s widow, Crystal Hefner, in the trailer, as she hints she has “something I want to talk to you about.” Wilkinson laments, “As I struggled to get ahead, my past comes calling back and I just want to move forward.”

At her very own brokerage, the reality personality finds herself at odds with a new agent who thinks Wilkinson “has something” for her boyfriend following her divorce from former NFL wide receiver Hank Baskett. “Last season, I moved on from my Playboy past and picked myself up after my divorce,” Wilkinson says in the trailer. “I am now a real estate agent. I’ve got my spot, now I’ve got to earn it.”

Wilkinson stepped out in Season 1 of Kendra Sells Hollywood as she got back on her feet from her divorce while trying to be the best mom she could be for daughter Alijah, 8, and son Hank IV, 13. Ahead of the series premiere, she told PopCulture of the new endeavor, “Hollywood ended a couple years ago and nobody was calling. I wasn’t getting any more deals. It was over for me in Hollywood. My 15 minutes were up, so I had to figure it out.”

“Being a mom of two and [having] no one to rely on, I have to provide,” Wilkinson continued. “I decided on real estate and to fully commit myself to it. So I decided that – I passed the real estate exam the first try and the cameras came back to film it all.” Season 2 of Kendra Sells Hollywood premieres Friday, May 26 on HBO Max, with two episodes dropping weekly through June 9. The entire first season, which originally debuted on discovery+, will be available on HBO Max beginning May 23.