Michelle Obama's remark about being single to CEO pal Brian Chesky on podcast gets Internet talking

Michelle Obama's remark about being single to CEO pal Brian Chesky on podcast gets Internet talking
Airbnb CEO Brian Chesky appeared on Michelle Obama's podcast (Screengrab/@michelleobama/YouTube)

LOS ANGELES, CALIFORNIA: Michelle Obama shared a humorous and flirtatious moment with Airbnb CEO Brian Chesky during the latest episode of her 'Michelle Obama: The Light Podcast', which she co-hosts with her brother, Craig Robinson.

As Chesky recounted a funny story about an Airbnb guest who obsessively refreshed the site until securing a booking in his home, Michelle couldn't resist chiming in with a teasing remark, reports Page Six.



 

Michelle Obama jokes about Airbnb CEO’s bachelor status in playful podcast moment

“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…” she said suggestively, leaving the rest to the imagination.

Chesky, 43, laughed off the comment, acknowledging that both Michelle and former President Barack Obama have tried to play matchmaker for him in the past.


AUSTIN, TEXAS - MARCH 13: Michelle Obama speaks onstage during a recording of the
Michelle Obama speaks onstage during a recording of the 'IMO with Michelle Obama & Craig Robinson' podcast during the 2025 SXSW Conference And Festival at Austin Convention Center on March 13, 2025 in Austin, Texas (Julia Beverly/WireImage)

“I’m very invested in Brian’s love life,” Michelle, 61, admitted, prompting more laughter. Chesky agreed, joking that Barack Obama has offered “a lot of relationship advice,” though the results are yet “to be seen.”

The billionaire tech executive, whose estimated net worth is $8.9 billion, has mostly kept his dating life private. He was previously in a long-term relationship with artist Elissa Patel, whom he met on Tinder, before they split in 2022.

Rumors briefly swirled in late 2023 linking him to model Brooks Nader, though insiders dismissed the pairing as casual.

Brian Chesky, CEO of Airbnb, Inc., attends the Allen & Company Sun Valley Conference on July 14, 2023 in Sun Valley, Idaho. Every July, some of the world's most wealthy and powerful figures from the media, finance, technology and political spheres converge at the Sun Valley Resort for the exclusive weeklong conference. (Photo by Kevin Dietsch/Getty Images)
Brian Chesky, CEO of Airbnb, Inc, attends the Allen & Company Sun Valley Conference on July 14, 2023 in Sun Valley, Idaho (Kevin Dietsch/Getty Images)

“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,” the source noted.

Internet reacts to Michelle Obama’s playful podcast banter with Brian Chesky

Former First Lady Michelle Obama welcomes the audience at Matriarch - An Evening with Tina Knowles at The Theater at MGM National Harbor on April 30, 2025 in National Harbor, Maryland (Photo by Shannon Finney/Getty Images)
Former First Lady Michelle Obama welcomes the audience at Matriarch - An Evening with Tina Knowles at The Theater at MGM National Harbor on April 30, 2025, in National Harbor, Maryland (Shannon Finney/Getty Images)

A lighthearted exchange between Michelle Obama and a longtime CEO friend on a recent podcast episode has sparked a wave of commentary across social media, with reactions ranging from amused to sharply critical.

A handful of critical users claimed it felt “attention-seeking” or “out of character” for Obama. 

“Michelle thirst for attention is so off putting!!” one user wrote.

“Flirty? Well that doesn't fit her personality. It's just silly. Next!” added another.

Some comments were more pointed, with users calling the podcast banter “pathetic” and accusing her of seeking the spotlight unnecessarily, with one writing, “She is one truly disgusting person. Why won’t she just go away? Why this constant need for attention?”

“I almost feel sorry for Barack,” another added.

This article contains remarks made on the Internet by individual people and organizations. MEAWW cannot confirm them independently and does not support claims or opinions being made online.

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