Michelle Obama gets flirty with Airbnb boss amid split speculation

Michelle Obama teases about being single while discussing love, cookies, and Airbnb with CEO Brian Chesky.

Former First Lady Michelle Obama sparked interest with a light-hearted remark during her “IMO” podcast, where she interviewed Airbnb co-founder and CEO Brian Chesky.

The episode featured friendly banter about relationships, cookies, and Chesky’s home — now listed on Airbnb.

During the conversation, Michelle joked about the idea of being single and booking a stay at Chesky’s house, which he recently opened to guests. "If I'm a single girl out there and I find out that Brian Chesky is single...," she began, teasingly. Her brother and co-host Craig Robinson quickly interjected, saying, "Here she goes. Right to the relationship."

Chesky’s Airbnb listing, which includes fresh cookies, coffee, and a golden retriever, has seen high demand, with weekends booked out months in advance. The tech executive hosts guests personally, often cooking for them on the first night and training together for "total muscle failure" after dessert.

Michelle warmly noted that both she and former President Barack Obama consider Chesky a close family friend, adding, “If I had a son, I would want my son to be Brian.” The discussion revealed that the Obamas have even attempted to set Chesky up in the past.

Chesky shared that Barack Obama has given him plenty of relationship advice, though he playfully declined to rate the former president’s matchmaking skills.

The episode showcased the Obamas’ bond with Chesky, blending warmth, humor, and glimpses into the personal lives of two high-profile figures. The exchange underscored Michelle Obama’s signature charm and her continued influence in media and pop culture.