‘If I Were a Single Girl’ – Michelle Obama’s Conversation with Airbnb CEO Raises Eyebrows (VIDEO) |

In a recent episode of her podcast, former First Lady Michelle Obama created quite a buzz by playfully expressing her thoughts on being single, particularly in the context of Airbnb CEO Brian Chesky. This light-hearted exchange has sparked intrigue, considering Chesky’s own venture into the rental market.

Chesky had previously announced in 2022 that he was renting out his home on Airbnb, stating, “Starting today, my home is now on Airbnb (yes, this is my actual home and I’ll be there when guests are here),” a move that certainly raised eyebrows and perhaps a few eyebrows more. This personal touch to his Airbnb listing has only added to the allure.

Starting today, my home is now on Airbnb (yes, this is my actual home and I’ll be there when guests are here) https://t.co/6XXFA7GNZ6 pic.twitter.com/xtKeJYIVrS

— Brian Chesky (@bchesky) November 17, 2022

During the podcast, Michelle humorously mused about the potential of being a single woman who could stay at Chesky’s home, saying, “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, have you ever—” The moment prompted laughter and a quip from her brother, Craig Robinson, who jokingly cautioned Chesky against feeling pressured.

“We’ve never talked about this,” Michelle added, highlighting the spontaneity of their conversation.

Robinson chimed in with comedic timing, “He just got here!” to which Chesky revealed that the Obamas had previously attempted to play matchmaker for him. “Her and her husband have tried to set me up before,” he noted, adding a layer of lightheartedness to the discussion.

“I’m very invested in Brian’s love life,” Michelle Obama declared, a statement that surely left listeners amused and perhaps a bit bewildered by the intertwining of personal and professional lives in such a public forum.

WATCH:

Michelle Obama said she’s “very invested” in Airbnb co-founder Brian Chesky’s love life. pic.twitter.com/KglLQzGnrX

— New York Post (@nypost) May 25, 2025

The conversation around this podcast episode has since attracted additional media scrutiny, including inquiries from Fox News regarding Michelle Obama’s candid remarks and the implications of her commentary.