Michelle Obama Gets Flirty as She Reveals What She’d Do if She Were ‘Single’ Amidst Divorce Rumors

For months now, speculation has been mounting that former President Barack Obama and former First Lady Michelle Obama are headed for a split.

Whispers of the Obamas living “separate lives” have circulated in both political and entertainment spheres.

This week, Michelle Obama added more fuel to the fire when she appeared to get flirty with Airbnb CEO Brian Chesky on her The Light Podcast, sparking widespread media and public reaction.

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During Wednesday’s podcast episode, Michelle, 61, interviewed Chesky, 43, alongside her brother and co-host Craig Robinson, 64. Early in the episode, Michelle appeared to make a playful — and surprisingly suggestive — comment that caught listeners off guard.

“You know, I have to say Brian if I’m a single girl out there and I find out that Brian Chesky is single and I could like stay in his house —,” she began, trailing off before her brother quickly stepped in.

“Here she goes, right to the relationship,” Craig interjected, trying to steer the conversation back to a more neutral tone. “Brian you don’t have to feel pressure.”

Rather than appearing embarrassed, Chesky responded with a calm familiarity, revealing, “Her and her husband have tried to set me up before.”

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Michelle didn’t back down. She continued the banter, admitting, “I am very invested in Brian’s love life.”

Michelle Obama admitted she’s “very invested” in Airbnb founder Brian Chesky’s love life. 👀 🎥: IMO with Michelle Obama pic.twitter.com/CvDH136O8E

— Page Six (@PageSix) May 21, 2025

Chesky, clearly caught off guard, awkwardly replied that he “appreciated” her interest.

While some listeners may have seen the moment as harmless fun, others viewed it as a sign of deeper issues in the Obama household. The timing is particularly curious given the current climate of speculation surrounding the couple’s marriage.

The former First Lady’s flirtatious tone comes on the heels of months of rumors that she and Barack have been leading increasingly separate lives.

These rumors intensified in January, when Michelle notably skipped both the funeral of former President Jimmy Carter and the inauguration of Donald Trump — the only living First Lady to miss both major events.

“I have been hearing this rumor that the Obamas are getting a divorce by reputable people,” political commentator Meghan McCain said on reporter Tara Palmeri’s podcast earlier this year.

“I’m not talking about TMZ, I’m not talking about Perez Hilton, although I love him, he’s my friend. I’m talking about like very serious journalists telling me that they’re hearing that the Obama divorce rumors are true.”

Palmeri, who has covered Washington politics for years, concurred. “We’ve heard that for a long time. Like I just heard that they live separate lives.”

Meghan McCain spills on Obama divorce rumors amid claims they ‘live separate lives pic.twitter.com/8tR3d3eQAt

— Simo Saadi🇺🇸🇲🇦 (@Simo7809957085) January 23, 2025

Michelle’s podcast behavior hasn’t helped quell the speculation.

Since launching The Light Podcast in March, Michelle has frequently taken jabs at Barack. Many of her comments paint their relationship in a less-than-flattering light — a shift that has not gone unnoticed.

Former Fox News host Tucker Carlson added his voice to the growing chorus of skepticism.

“Michelle really dislikes her husband, and it’s super obvious,” Carlson said on his own program. “I’m not just saying that to be catty. I think I’m trying to feel compassion for her but her hostility toward the guy is unbelievable.”

Megyn Kelly, another former Fox News anchor, echoed this sentiment.

“Everything Michelle says about her husband is negative,” she noted.

“I almost never say negative things about Doug,” Kelly added, referring to her husband Doug Brunt. “He’s not perfect but when I think about him, I don’t immediately go to whatever is negative. I go to what’s positive and what I love about him.”

While Barack Obama has remained silent on the divorce rumors, Michelle has made various attempts to dismiss them.

Tucker Carlson has claimed Michelle Obama hates her husband Barack, and that people like her, who aren’t happily married, are to blame for society’s collapse. pic.twitter.com/tc3wxYcMG5

— 🇺🇸⭐️OUR-VOICES⭐️🇺🇸 (@iswho) April 30, 2025

Still, moments like her recent exchange with Chesky only seem to deepen public suspicion.

Whether Michelle’s comments were just playful banter or a subtle public signal of personal discontent is anyone’s guess.

But for many, the optics couldn’t be worse — particularly given how frequently Michelle appears to take thinly veiled shots at her husband in her public appearances.

As speculation continues to build, one thing is clear: Michelle’s flirtatious moment with Chesky isn’t going to make the rumors disappear.

If anything, it’s reigniting the conversation about what’s really going on behind closed doors with America’s former first couple.

Only time will tell if Michelle and Barack Obama’s 33-year marriage can withstand the growing scrutiny and the increasingly public signs of strain.

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