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Michelle Obama | Source: Getty Images
Michelle Obama | Source: Getty Images

Michelle Obama Called Out for Flirty Moment With Airbnb's Brian Chesky

Olena Mosiichuk
May 26, 2025 - 08:19 A.M.

Michelle Obama is under scrutiny after making what some called a flirty remark during a podcast episode featuring Airbnb CEO Brian Chesky, prompting online speculation about her relationship with husband Barack Obama.

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Viewers of Michelle Obama's latest podcast episode were taken aback by comments she made during a lighthearted conversation with Brian Chesky, the CEO of Airbnb. Some social media users criticized the former First Lady’s tone, claiming it was overly suggestive for a married woman.

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The episode, co-hosted by Obama and her brother Craig Robinson, featured Chesky discussing a new initiative in which he opens his own home to Airbnb guests–while staying in the home himself. The listing includes amenities like freshly baked chocolate chip cookies, a golden retriever, a home gym, and freshly brewed coffee.

The home, originally offered on a limited number of weekends, was quickly booked out. In response, Chesky announced he would expand the available dates for the rest of the year to accommodate more guests.

Brian Chesky during the "IMO" podcast with Michelle Obama and Craig Robinson, released May 21, 2025 | Source: YouTube/Michelle Obama

Brian Chesky during the "IMO" podcast with Michelle Obama and Craig Robinson, released May 21, 2025 | Source: YouTube/Michelle Obama

During their conversation, Obama noted that this was her first time formally interviewing Chesky, despite their long-standing friendship. She described him as a close friend of both hers and former President Barack Obama.

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The segment that drew the most attention came after Chesky revealed that someone was so eager to stay with him at his home that they checked his page consistently to find a spot. In response, Obama joked: "I have to say, Brian, if I'm a single girl out there, and I find out that Brian Chesky is single, I can like, stay in his house. Have you ever..."

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Brian Chesky attends the "IMO" podcast with Michelle Obama and Craig Robinson, released May 21, 2025 | Source: YouTube/Michelle Obama

Brian Chesky attends the "IMO" podcast with Michelle Obama and Craig Robinson, released May 21, 2025 | Source: YouTube/Michelle Obama

Her brother quickly cut her off, quipping that she was steering the conversation into relationship territory. Chesky added, "Her and her husband have tried to set me up before." Obama responded, "I'm very invested in Brian’s love life."

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The exchange sparked a wave of online reactions. "Isn't she married... how is this appropriate [sic]" one person wrote. Another commented, "Interesting looking at Michelle Obama here, she looks like she wants to be young again."

Others were more blunt. "Really really off the hook. Totally inappropriate," a third person said. "Just come out and say you're single already," someone added, referencing persistent rumors about the Obamas' marriage.

Obama has previously addressed such speculation. In a recent appearance on "The Diary of a CEO podcast with Steven Bartlett," she dismissed the divorce rumors, saying, "If I were having problems with my husband, everybody would know about it."

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