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In the May 21 episode of the IMO podcast, hosts Michelle Obama and Craig Robinson were joined by Airbnb CEO Brian Chesky, where he claimed that former U.S. President Barack Obama had tried to "set" him up on dates before.
When Craig asked whether Barack was good at fixing him up on dates, Brian Chesky responded:
"We'll see, I guess, remains to be seen, but, yeah, he's definitely very invested, and he's provided a lot of relationship advice to me, actually."
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Elsewhere in the podcast, Michelle asked Brian Chesky about the best dating advice Barack has given him. Chesky recalled a moment when he was about to go on a date with someone and told Barack that his date met all the qualities he was looking for in a partner.
Instead of agreeing, the former U.S. president advised him to stay away from the idea of dating based on a checklist of qualities and instead focus on the actual connection with a person.
"[Barack said] you're not dating a checklist. You're dating a real person, and the real person makes you feel a certain way. And I think it was like a really, really important piece of advice."
"I've not had a lot of success with the tools"—Brian Chesky reflects on dating in the modern world
Further in the podcast, Michelle asked the Airbnb CEO about his experience with dating apps.
"How are you using these tools to find your life partner?" Michelle Obama questioned.
Brian Chesky explained that he has had a better experience meeting people through friends than meeting them online.
"I've not had a lot of success with the tools, if I'm being honest. The best success I've had with meeting people is the old-fashioned way through other friends," Chesky said.
Chesky further opened up about his conversation with his best friend and Bumble founder Whitney Wolfe Herd about how online dating has largely become a world of "judgment," where people make split-second decisions by swiping left and right, adding:
"If people say have a type, the question I'd have back is, you met enough people in the world to know there's a type."
Chesky further explained that people's idea of having a type is based on their limited experiences and the few people they've met, adding,
"So many people end up with people that aren't 'their type.'"
He further expressed that one should approach people with curiosity and not judgment, adding:
"Instead of swiping, we need to discover and find what's really interesting to people, and so I think that's probably one of the things that we need to do more of."
As reported by Page Six on May 21, 2025, Brian Chesky is currently unmarried. He was previously in a relationship with artist Elissa Patel for about five years; however, the couple separated in 2022.
