US former first lady Michelle Obama sparked interest during her podcast by contemplating the idea of single women having the chance to stay at Airbnb co-founder Brian Chesky 's residence.
At the podcast, the former first lady revealed that she and Barack Obama consider Chesky a close friend, stating, "If I had a son, I would want my son to be Brian."
Few years back, Chesky has opened his own home as an Airbnb, writing, "Starting today, my home is now on Airbnb (yes, this is my actual home and I’ll be there when guests are here)."
During their discussion about his hosting practices, Chesky described preparing dinner for guests on their first evening. When he mentioned his famous cookies, Michelle Obama enquired why she hadn't sampled them yet. Chesky responded that she would need to book a stay to taste them.
Chesky shared positive experiences with his guests, mentioning that one person made extraordinary efforts to secure a booking.
The conversation took an interesting turn when Michelle Obama speculated about single women having the opportunity to stay at his house. "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 -"
This prompted her brother Robinson to interject, "Here she goes... Right to the relationship. Brian, you don't have to feel pressure."
Chesky revealed that both Michelle and Barack Obama had previously attempted to match him with potential partners. Mrs Obama openly admitted, "I'm very invested in Brian's love life."
When questioned about Barack Obama's matchmaking abilities, Chesky diplomatically responded that it "remains to be seen." However, he acknowledged that the former president has been "definitely very invested, and he's provided a lot of relationship advice to me, actually."
At the podcast, the former first lady revealed that she and Barack Obama consider Chesky a close friend, stating, "If I had a son, I would want my son to be Brian."
Few years back, Chesky has opened his own home as an Airbnb, writing, "Starting today, my home is now on Airbnb (yes, this is my actual home and I’ll be there when guests are here)."
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 their discussion about his hosting practices, Chesky described preparing dinner for guests on their first evening. When he mentioned his famous cookies, Michelle Obama enquired why she hadn't sampled them yet. Chesky responded that she would need to book a stay to taste them.
Chesky shared positive experiences with his guests, mentioning that one person made extraordinary efforts to secure a booking.
The conversation took an interesting turn when Michelle Obama speculated about single women having the opportunity to stay at his house. "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 -"
Michelle Obama says if she was a “single girl” she would love to stay at Airbnb CEO’s home.
— Oli London (@OliLondonTV) May 22, 2025
“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…” pic.twitter.com/UPvv55NZph
This prompted her brother Robinson to interject, "Here she goes... Right to the relationship. Brian, you don't have to feel pressure."
Chesky revealed that both Michelle and Barack Obama had previously attempted to match him with potential partners. Mrs Obama openly admitted, "I'm very invested in Brian's love life."
When questioned about Barack Obama's matchmaking abilities, Chesky diplomatically responded that it "remains to be seen." However, he acknowledged that the former president has been "definitely very invested, and he's provided a lot of relationship advice to me, actually."
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