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Michelle Obama Has Flirty Interaction With CEO Despite Setting the Record Straight About Barack Obama Marriage

Photo of Michelle Obama, Brian Chesky.
Source: @MichelleObama/youtube;MEGA

Michelle Obama had a flirty moment with Airbnb CEO Brian Chesky on her podcast.

May 21 2025, Published 6:35 p.m. ET

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Michelle Obama seemed to get a little flirty with Airbnb CEO Brian Chesky.

During the Wednesday, May 21, episode of her and her brother Craig Robinson's "IMO" podcast, Chesky spoke recalled a story in which one Airbnb user kept refreshing the website until they got to book time in his abode.

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michelle obama airbnb ceo imo podcast
Source: @MichelleObama/youtube;MEGA

Michelle Obama spoke to Brian Chesky about his relationship status.

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“I have to say, Brian, if I’m a single girl out there and I find out that Brian Chesky is single and I can like, stay in his house…” Obama, who is married to Barack Obama, cheekily said.

“I’m very invested in Brian’s love life,” Michelle, 61, admitted.

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brian chesky airbnb mega
Source: MEGA

The businessman said the ex-president 'provided a lot of relationship advice' to him.

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The 43-year-old businessman joked the ex-president's matchmaking skills "[remain] to be seen."

“He’s definitely very invested and he’s provided a lot of relationship advice to me actually,” Chesky added.

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The entrepreneur has never been married, but he dated Elissa Patel for nearly five years before calling it quits in 2022.

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brian chesky and gwyneth patrow
Source: MEGA

Michelle Obama made a cheeky joke to the CEO.

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For her part, Michelle has fueled divorce rumors after she skipped Donald Trump's inauguration.

"You know, as a box-checking person who has been checking her whole life, doing the right thing, trying to always be an example, always going high … I think I just told myself, ‘I think I’ve done enough of that,’ and if I haven’t, then I never will," she previously explained.

"It’ll never be enough. So let me start now," she said about how she's starting to put up more boundaries later in life.

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michelle obama airbnb ceo imo podcast
Source: @MichelleObama/youtube

The star is married to Barack Obama.

Though the former president went to Inauguration Day in January alongside other past president's, Michelle didn't mind sitting out on that opportunity.

"At the same time I met Barack Obama, he showed up in my life as the opposite of a box checker, but somebody that I describe in my book as an 'ultimate swerver.' He did nothing by the book. He was brilliant and interesting," she recalled. "He was really trying to unpack life in a way that people in my generation weren't trying to do...and I thought, I have to do something more before I settle on this [career], and I think Barack helped give me the courage."

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