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Michelle Obama has flirty exchange with CEO pal on podcast: ‘Very invested’

May 21, 2025
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Michelle Obama has flirty exchange with CEO pal on podcast: ‘Very invested’
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Michelle Obama in March.
Michelle Obama (seen here in March) had a flirty exchange with Airbnb CEO Brian Chesky. Getty Images

Michelle Obama wouldn’t mind booking a stay with Airbnb CEO Brian Chesky.

The former first lady had a flirty exchange with the single tech executive on Wednesday’s episode of her and her brother Craig Robinson’s “IMO” podcast.

Chesky rehashed a hilarious story in which an Airbnb user repeatedly refreshed the website thousands of times until they got to book a stay in his home — prompting Obama to voice her understanding for his overly eager house guest.

The former first lady’s interaction with Chesky unfolded on her podcast with Craig Robinson, “IMO.” Michelle Obama/YouTube
Brian Chesky in May.
Chesky (seen here in May) told the story of an Airbnb user who refreshed the website thousands of times until they got to book a stay at his home. AFP via Getty Images

“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 cheekily said without finishing her thought, suggesting that she finds him to be a great catch.

Chesky interrupted to acknowledge that Michelle and her husband, former president Barack Obama, have tried to set him up with potential suitors on numerous occasions.

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

Michelle Obama in April.
“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 said, without finishing her thought. IMO Podcast/YouTube
Brian Chesky on a walk.
Chesky said that Michelle and Barack Obama are constantly trying to set him up on dates. Ben Rothstein

The billionaire bachelor, 43, joked that Barack’s skills at matchmaking “[remain] to be seen.”

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

The Silicon Valley entrepreneur — who has a reported net worth of $8.9 billion — has never been married, though he dated artist Elissa Patel for nearly five years before splitting in 2022.

Michelle Obama on a podcast.
The “Becoming” author said she is “very invested” in Chesky’s dating life. IMO with Michelle Obama
Brian Chesky in May.
The tech exec (seen here in May) has never been married. AFP via Getty Images

The exes allegedly met on the Tinder dating app.

Chesky has mostly kept his dating life quite private, though he did spark romance rumors with Brooks Nader last Fall after they were seen showing PDA at a Halloween party.

Insiders told Page Six at the time that their relationship was “nothing serious.”

Brian Chesky in May.
Chesky (seen here in May) previously dated Elissa Patel. AFP via Getty Images
Brian Chesky in May.
He has a reported net worth of $8.9 billion. Getty Images for Airbnb

“Brian and Brooks run in similar social circles and have hung out a few times in New York. It was very casual and they are not dating,” a source said.

Meanwhile, the “Becoming” author and Barack, 63, have been married since 1992.

The couple are parents to daughters Sasha, 23, and Malia, 26.

The post Michelle Obama has flirty exchange with CEO pal on podcast: ‘Very invested’ appeared first on Page Six.

Tags: airbnbBarack Obamabillionairesbrian cheskycelebrity datingcelebrity friendshipsMichelle ObamaPodcasts
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