In a fun, unfiltered premiere episode, Khloé Kardashian sits down with her “silly” sister Kylie Jenner — sharing laughs, drinks, and candid confessions that set the tone for a more personal new season.
Khloé Kardashian is back with a brand-new season of her hit podcast Khloé in Wonder Land — and this time, she’s bringing family, fun, and a little bit of tequila to the mic. The 41-year-old reality star kicks off season two with her youngest sister, Kylie Jenner, 28, in an episode that promises honesty, humor, and sisterly chaos.
In an exclusive conversation with PEOPLE, Kardashian revealed that Jenner’s guest appearance marks a surprising first for the billionaire beauty mogul. “What I didn’t realize — Kylie has never done a podcast before,” Khloé admitted. “I was like, ‘Oh, maybe I should have known that before I interviewed you!’”
Unlike the first season’s structured, expert-driven format, Khloé in Wonder Land season two takes a more relaxed and intimate approach. Kardashian says she wanted the new episodes to feel less like interviews and more like genuine conversations — especially when it comes to family and friends.
“Obviously, because it’s my sister, I didn’t want to ask things like, ‘Where did you grow up?’ That’s stupid,” Khloé said with a laugh. “We were supposed to be doing makeup together, but that didn’t really happen — so we just got drunk.”
As the cocktails flowed, so did the conversation. Khloé didn’t hold back, asking Kylie everything from pregnancy memories they shared to lighthearted personal quirks. “I asked her questions I think other people would love to ask her, but if they got ten minutes with her, they probably wouldn’t,” she explained. “Some were really personal, others just silly — like, ‘You keep our family chat on mute all the time? Okay, good to know!’”
Kardashian also opened up about why Kylie is one of her favorite people to interview. “She’s so silly, and I love that she doesn’t take herself seriously,” she said. “Like, if she trips, she just smiles and goes with it. I’m always like, ‘God, why can’t I respond to embarrassing moments like that?!’”
The chemistry between the sisters — who have weathered fame, family drama, and motherhood side by side — shines through in the episode, blending raw honesty with the signature Kardashian humor fans adore.
Produced by Dear Media, Khloé in Wonder Land season two premieres November 12 and is available on all major podcast platforms.
