If the world was amazed by the oratory skills of former President Barack Obama, they were mind blown when they heard Michelle Obama speak. No wonder she, after writing two best sellers, decided to opt for a podcast with her brother Craig.
In the latest episode of IMO with Michelle Obama and Craig Robinson, former First Lady Michelle Obama had a playful exchange with Airbnb CEO Brian Chesky. A cheeky banter that caught social media’s attention.
The sibling podcast is known for its casual tone and hilarious banter. Following the same pattern, Michelle Obama and Brian got talking, and the casual give and take was endearing.
However, it took an unexpected turn when the topic of Chesky’s Airbnb listing came up.
Chesky told a story about a fan who obsessively refreshed Airbnb in hopes of booking a stay at his personal residence. Obama was clearly amused, as were the listeners. She chimed in with a cheeky remark: “If I’m a single girl out there and I find out that Brian Chesky is single, and I can … stay in his house …”
Her flirty comment drew laughter from her brother and co-host Craig Robinson. Without missing a beat, Craig responded, “Here she goes. Right to the relationship.”
Michelle Obama admitted she’s “very invested” in Airbnb founder Brian Chesky’s love life. 👀 🎥: IMO with Michelle Obama pic.twitter.com/CvDH136O8E
— Page Six (@PageSix) May 21, 2025
The remarks were all innocent and lighthearted, but nothing ever is when there are celebrities involved. It caused a stir online, and viewers started interpreting it in various ways. This was particularly in light of ongoing rumours about the Obamas’ marriage.
The episode’s tone remained light and humorous. Robinson didn’t miss a chance and continued to rib both Michelle and Chesky throughout the segment. Chesky himself revealed that this wasn’t the first time the Obamas had taken an interest in his romantic life.
“Michelle and her husband have tried to set me up before,” he shared. This went on to show the close and long-standing friendship the couple shared with the host.
Michelle Obama added that she was very invested in Brian’s love life. It reinforced the idea that the earlier remark was more about familiarity and fun than any serious flirtation. The dynamic among the three hosts painted a picture of friendship, not of scandal.
Brian Chesky also noted that former President Barack Obama has offered him dating advice in the past. This revelation added another layer to the story. It indicated that the bond between Barack and Michelle Obama, and Chesky goes well beyond mere acquaintance.
However, when viewed in isolation, the comment has taken on a life of its own. This goes true for social media commentators and column writers who can write a whole segment based on one sentence or a look.
#MichelleObama‘s telling fans where she’d go if she were single 👀😏☕ MORE ON WHY SHE SPILLED THE TEA: https://t.co/xBAOIuLOfV
🎥: IMO with Michelle Obama and Craig Robinson pic.twitter.com/NTCwgv0F3k
— TMZ (@TMZ) May 21, 2025
And that’s exactly how it went. Many listeners took the podcast banter at face value and listened to the whole conversation. However, some observers were quick to link Michelle’s flirtatious remark to recent speculation surrounding the apparent state of the Obamas’ marriage.
Both Michelle Obama and Barack Obama have publicly denied any marital discord. Yet, the couple remains under public scrutiny. That’s why even a seemingly innocent joke sparked headlines.
For a couple as iconic as the Obamas, managing perception is as important as managing policy. Even playful moments on a podcast can become part of a broader narrative. No matter the authenticity of the narrative.
