Former first lady Michelle Obama drew laughter and curiosity during a recent episode of her podcast when she touched on her marriage and playfully imagined herself as a single guest at Airbnb CEO Brian Chesky’s home.

Obama hosted Chesky on her podcast to discuss his unique Airbnb listing, share light-hearted banter, and clarify public speculation about her marriage alongside her co-host and brother, Craig Robinson, as Fox News reports.

The conversation aired on a Wednesday episode of IMO, Michelle Obama's podcast, where she and Robinson interviewed Brian Chesky, co-founder and CEO of Airbnb. Obama greeted him warmly and told listeners that Chesky is a close friend and someone she would "want as a son" if she had one. The familiarity between the three helped set the stage for a relaxed and personal discussion.

Chesky shares details of personal life, home

During the episode, Chesky shared details about his one-of-a-kind Airbnb listing -- his actual home, which he opens to guests while living there during their stay. "Starting today, my home is now on Airbnb," he stated. He added he personally welcomes visitors and participates in their experience.

The CEO described several special amenities he includes for guests, such as freshly brewed coffee, chocolate chip cookies he bakes himself, and time with his golden retriever. One unique component includes physical workouts, with Chesky joking, "We will work out together and train until total muscle failure (after we’ve eaten lots of cookies)."

Chesky explained that his home was immediately in high demand, with reservations for the first three months of the year sold out before he officially announced the listing. He shared with Obama that additional weekends will become available later in the year as interest builds.

Hypothetical single life discussed

The conversation turned humorous when Michelle Obama playfully suggested what it might be like if she were single and looking to stay at Chesky’s Airbnb. "If I'm a single girl out there," she said while referencing Chesky’s eligibility, "and I find out that Brian Chesky is single, and I can, like, stay in his house, have you ever —"

Her brother, Craig Robinson, quickly interjected, joking, "Here she goes," followed by, "Right to the relationship," signaling the direction the conversation had taken. He reassured Chesky, saying he didn’t need to feel pressured by the intimacy of the topic.

Laughing off the moment, Obama addressed the humorous tone but also took the opportunity to clarify any speculation about her personal life. She indirectly responded to circulating rumors, affirming that her marriage to former President Barack Obama remains intact.

Obamas as matchmakers

The dialogue shifted once more into Chesky’s personal life and the Obamas’ history of interest in his relationships. Chesky revealed, "She and her husband have tried to set me up before," acknowledging the couple’s efforts to help him find a partner.

Michelle confirmed her enthusiasm about Chesky’s dating prospects, saying she’s "very invested in Brian’s love life." Her interest appeared genuine, yet she still delivered in a fun, friendly manner throughout the interview.

Chesky spoke positively about Barack Obama’s involvement in his love life, describing the former president as being "definitely very invested." He also shared that Barack has provided a significant amount of romantic advice to him, although when asked if Barack has been a successful matchmaker, Chesky replied, "It remains to be seen."

Mixing business, humor, friendship

Throughout the episode, Michelle Obama maintained a balance of serious interest and light-hearted interaction, telling Chesky, "I usually don't get to talk to you in an interview format, so let's pretend like it's just us at dinner." This casual tone helped make the discussion feel approachable, even while involving topics such as dating, business hosting, and public speculation.

The episode reflects the friendly, layered relationship among the Obamas, Robinson, and Chesky, one built on years of trust and continued personal investment. Obama’s comment that she would want Chesky as a son highlighted how well regarded he is by her family.

While the interview began with Chesky’s career as a tech executive and Airbnb host, the discussion quickly evolved to highlight the comfort and rapport among the guests, blending personal updates with public curiosity and humor.

Podcast gains fan base

This episode of IMO stood to fans out not just for its engaging conversation but also for its mixture of insight and spontaneity. The candid tone offered a rare look into a business leader’s home life and relationships -- and the role high-profile friends may play in shaping them.

The popularity of the podcast among admirers of the former first lady has been attributed in part to Michelle Obama’s ability to connect casually with her guests, as shown in this interview. Listeners continue to appreciate her efforts in making topics like business, relationships, and even rumors relatable and light-hearted.

With more weekends to be opened for guests at Chesky’s Airbnb and further episodes of IMO on the horizon, followers will likely continue tuning in to see what other unexpected conversations might come up.