Michelle Obama Jokes About Being Single and Booking a Stay at Airbnb CEO Brian Chesky’s House

Michelle Obama made headlines after a funny and unexpected moment on her recent podcast episode. While speaking with Airbnb CEO Brian Chesky, the former First Lady imagined what it would be like to be single and book a stay at his home. The conversation happened during the latest episode of her “IMO” podcast, co-hosted by her brother Craig Robinson.

Chesky recently opened up his personal home as an Airbnb. He announced the news on social media, saying, “Yes, this is my actual home and I’ll be there when guests are here.” The listing includes fun details like freshly baked cookies, a golden retriever, and workout sessions with the host himself.

The home is already wildly popular. Chesky said all available weekends in January, February, and March were booked immediately. He promised to add more dates throughout the year for those who missed out.

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Michelle Obama Gets Playful About Booking a Stay

On the podcast, Michelle joked about the idea of being a single woman booking a visit. She said, “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…”

Her brother Craig jumped in, saying, “Here she goes. Right to the relationship.” He teased both of them as the playful banter continued.

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Michelle responded, “We’ve never talked about this.” Chesky laughed and mentioned that the Obamas had tried to set him up before. “Her and her husband have tried to set me up,” he said.

Michelle confirmed, “I’m very invested in Brian’s love life.”

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Craig then asked if Barack Obama was good at matchmaking. Chesky answered, “It remains to be seen.” He did admit that Barack had given him relationship advice and was “definitely very invested.”

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Michelle shared her excitement about the podcast moment. “Let’s pretend it’s just us at dinner somewhere,” she said as she welcomed Chesky.

The conversation also covered how Chesky hosts his guests. He shared that he prepares dinner for them on the first night. When he brought up his famous cookies, Michelle asked, “Why haven’t I had any cookies?” Chesky replied, “You’ll have to book a stay.”

Fans Loved the Lighthearted Chat

The playful exchange quickly became a highlight of the podcast. Fans praised the relaxed and humorous tone. Many enjoyed hearing Michelle Obama show her fun and curious side. Others were surprised to learn about Chesky’s personal hosting habits and how much the Obamas care about his dating life.

Michelle also revealed how close she and Barack are with Chesky. She said, “If I had a son, I would want my son to be Brian.”

This episode gave fans a unique and fun look into the personal connections between public figures. It also reminded everyone that even former First Ladies enjoy joking about cookies, dating, and Airbnb stays.