Khloé Kardashian & Kylie Jenner's Tipsy Podcast Debut

Sister duo Khloé and Kylie got refreshingly candid — and a little tipsy — during Kylie's first-ever podcast appearance on 'Khloé in Wonder Land' season two.

TL;DR: The Quick Scoop

Kylie Jenner made her podcast debut on Khloé Kardashian's 'Khloé in Wonder Land' season 2, which launched November 12, 2025.
The sisters opted for cocktails during recording to foster a more relaxed and intimate conversation.
They reminisced about their viral 2019 "Drunk Get Ready with Me" video and tackled surprisingly personal questions.

Kylie Jenner's Unconventional First-Ever Podcast Appearance

"I'm, like, wasted! It's hitting me," Kylie, 28, announced just minutes into the podcast. Her older sister, Khloé, 41, playfully responded, "Breaking news, me too!" This candid exchange perfectly set the tone for an episode that saw Kylie Jenner make her first-ever podcast appearance, joining her sister Khloé Kardashian on the second season premiere of 'Khloé in Wonder Land'.

The highly anticipated episode, which premiered on November 12, 2025, marked a significant moment for Kylie, who had never before been a guest on a podcast. Khloé, taken by surprise by this fact, revealed that this unique circumstance led them to ditch conventional interview plans and instead opt for a more informal, cocktail-fueled chat. Source: People, "Khloé Kardashian spills beans on 'drunk' interview with Kylie Jenner," November 12, 2025.

From Viral YouTube Drunkenness to Podcast Confessions

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The idea of Khloé and Kylie getting tipsy for a public recording isn't entirely new territory for fans. Khloé herself brought up their legendary 2019 "Drunk Get Ready with Me" video on Kylie's YouTube channel, a sensation that has racked up an impressive 27 million views. During that infamous shoot, the sisters reportedly downed 18 shots between them. Khloé humorously recalled blacking out in the parking garage afterward, requiring Kylie's security to escort her home. Source: Khloé in Wonder Land/YouTube, "Kylie's security had to take me home, and I had to f--king hold it together for security," Undated.

This time around, their alcohol intake was considerably less dramatic. Before hitting record for the podcast, Khloé shared that they split just "half a shot of vodka and half a martini." Kylie, reflecting on their past antics, noted the stark difference in their current drinking habits, admitting, "I've taken one shot," compared to the six she claimed in their original viral video. Later, during the recording, Khloé took another "half shot," while Kylie opted for a "big gulp" of her martini. This controlled approach allowed for candidness without a complete blackout.

Spilling the Tea: What Happens When Sisters Get Really Real

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Khloé's decision to forgo a traditional interview structure was deliberate. When speaking to media outlets, she explained that asking her own sister generic questions like "Where'd you grow up?" would be "stupid." Instead, she aimed for "random questions that I think other people would love to ask her, but if they got 10 minutes with her, they probably wouldn't." This approach meant delving into genuinely personal topics, offering listeners an unfiltered glimpse into their lives and sibling dynamic.

The conversation covered a broad range of subjects, from shared experiences during their pregnancies to lighter, more relatable inquiries. Khloé teased some specific revelations, like Kylie's "silly things" and even how she handles family group chats. "I asked her everything, questions about the stuff that we went through during our pregnancy together, all the way to, 'When you're alone at night, what apps do you scroll through?'" Khloé shared. Source: People, "Kylie Jenner is making her first ever podcast appearance...," November 11, 2025. She even got Kylie to confess, "'You keep our family chat on mute all the time? Okay, good to know!'"

"Obviously because it's my sister, I didn't want to ask things like, 'Where'd you grow up?' That's stupid. So then we were supposed to be doing makeup together, but that didn't really happen, so we just got drunk."

— Khloé Kardashian on her approach to interviewing Kylie Jenner

Addressing the Unconventional Interview Approach

Some might raise an eyebrow at the idea of hosts and guests drinking during a podcast, questioning its professionalism or purpose. However, Khloé explicitly articulated her reasoning: she wanted to bypass the superficiality often found in celebrity interviews, especially with a family member. The shared drinks were a calculated choice to break down barriers, allowing both sisters to relax and genuinely connect, leading to insights that a more formal setting simply wouldn't yield. This intentional casualness served as a tool for authenticity, not an oversight.

Another perspective might suggest this entire "tipsy chat" is simply another publicity stunt. While launching a new season with a high-profile guest naturally garners attention, the Kardashians have a long history of sharing highly personal and often unvarnished moments, from their reality TV show to their individual social media channels. The viral success of their previous "drunk" content indicates that fans appreciate their willingness to be less polished. This podcast episode, therefore, aligns with their established brand of transparency, suggesting a genuine effort to offer an engaging, relatable experience to their audience, rather than just a clickbait headline.

Example of Candid Sisterly Questions

Imagine you're trying to catch up with a sibling you see all the time. You wouldn't hit them with "Where did you grow up?" right? You'd dive into the real stuff, the funny quirks, the shared memories. That's exactly what Khloé aimed for. For instance, you might ask your sister, "Remember that time we tried to bake a cake for mom and accidentally used salt instead of sugar, and she pretended it was delicious?" It's a question only you could ask to get a genuine laugh and a relatable story that's deeply rooted in shared experience, cutting through any formality. That’s the kind of spontaneous, personal gold Khloé was digging for.

The New Vibe for 'Khloé in Wonder Land' Season Two

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Kylie's episode isn't just a standalone event; it signals a new direction for 'Khloé in Wonder Land' itself. Khloé revealed that season two is set to be "a little looser" and more conversational. Unlike the first season, which often featured interviews with experts, this new iteration will welcome more family members and close friends into the fold. This shift promises a more intimate and less "talk show-y" feel, as Khloé described it.

The goal is to have guests "who are still really fascinating, but who are also comfortable engaging in a conversation with me," Khloé explained. She also hinted at more solo episodes based on listener-submitted topics, indicating a stronger connection with her audience. This pivot towards familiar faces and more personal dialogue is designed to offer deeper, more authentic insights, making each episode feel like a chat among friends.

Practical Takeaways for Listeners and Fans

Expect Unfiltered Kylie: This is a rare chance to hear Kylie Jenner in a truly relaxed, personal setting, free from a curated persona.
A More Intimate Podcast: 'Khloé in Wonder Land' season two is embracing a looser, more conversational format, focusing on Khloé's inner circle.
Relatable Sibling Dynamics: Even among mega-celebrities, the playful banter and personal revelations highlight universal sibling experiences.
Authenticity Over Formality: Khloé's choice to break traditional interview norms proves that sometimes the best content comes from genuine, unscripted moments.

FAQ: Your Questions Answered

Q1: Where can I listen to "Khloé in Wonder Land"? A: "Khloé in Wonder Land" is available wherever you typically get your podcasts. The second season, featuring Kylie Jenner, premiered on November 12, 2025.
Q2: Was this truly Kylie Jenner's first podcast? A: Yes, Khloé Kardashian confirmed that she was unaware Kylie had never been on a podcast as a guest before, making this her official debut.
Q3: Why did Khloé and Kylie decide to drink during the recording? A: They chose to share cocktails to make the conversation more relaxed and candid. Khloé felt standard interview questions wouldn't work well with her own sister, so the drinks helped facilitate a more genuine chat.
Q4: What kind of topics did they discuss on the podcast? A: The sisters covered a range of personal and "random" topics, including shared pregnancy experiences, what apps Kylie scrolls through at night, and even her habit of muting the family group chat.

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