Barack Obama Offers Surprising Dating Advice Amidst Rumors He’s Divorcing Michelle

As the rumor mill heats up with speculation about the state of Barack and Michelle Obama’s marriage, an unexpected revelation about dating advice from the former president is adding a new twist to the conversation.

Despite months of whispers that the Obamas are living “separate lives” and may be heading toward divorce, Barack recently emerged—albeit indirectly—with candid thoughts on what it means to truly connect with someone romantically.

The surprising insight came during a recent episode of Michelle Obama: The Light Podcast (formerly known as the IMO podcast), co-hosted by Michelle and her brother Craig Robinson.

Trump’s Sovereign Wealth Fund: What Could It Mean For Your Money?

The guest was none other than Brian Chesky, the 43-year-old CEO of Airbnb and a longtime mentee of Barack Obama.

As it turns out, their mentor-mentee relationship has included discussions that go far beyond business and leadership—diving into the personal and even romantic.

“One time I was like — I met somebody and I was about to go on a date with — I went on a date with them and I remember telling him like, ‘Oh my God, she checks all the boxes and like this, this, this, this, this,’” Chesky recounted on the show.

#MichelleObama‘s telling fans where she’d go if she were single 👀😏☕ MORE ON WHY SHE SPILLED THE TEA: https://t.co/xBAOIuLOfV

🎥: IMO with Michelle Obama and Craig Robinson pic.twitter.com/NTCwgv0F3k

— TMZ (@TMZ) May 21, 2025

This Could Be the Most Important Video Gun Owners Watch All Year

“And I remember him saying something. He said, ‘It’s not a checklist.’”

Chesky continued, quoting the former president’s perspective: “He’s like, the right person is someone where they’ve got this weird laugh or snort and you find it really funny. … It’s like, in other words, it’s not necessarily what you think you’re looking for. And you’re not dating a checklist, you’re dating a real person. And the real person makes you feel a certain way. I think it was like a really, really important piece of advice.”

This heartfelt wisdom came at a particularly intriguing moment.

For months, whispers have been growing louder that the Obamas’ 33-year marriage may be on the rocks.

These rumors gained momentum earlier this year when Michelle noticeably skipped major public events that drew attention—including the funeral for former President Jimmy Carter and the inauguration of Donald Trump.

As the only living former First Lady to miss both, Michelle’s absence raised eyebrows and fueled speculation about deeper personal issues.

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

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

“I have been hearing this rumor that the Obamas are getting a divorce by reputable people,” conservative political commentator Meghan McCain shared during an episode of reporter Tara Palmeri’s podcast back in January.

“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,” McCain added.

Tara Palmeri, who has covered Washington politics for years, didn’t shy away from the claim either. “We’ve heard that for a long time,” she said. “Like I just heard that they live separate lives.”

The rumors haven’t stopped at the idea of separation. In fact, they’ve escalated into speculation that Barack has already moved on—romantically.

For months, gossip sites and some media outlets have buzzed about a possible secret relationship between Barack and actress Jennifer Aniston.

The claims became so persistent that Aniston herself was asked about them during a sit-down with Jimmy Kimmel last October.

After watching this, I’m totally convinced that the story about Jennifer Aniston and Barack Obama is true!
What about you? pic.twitter.com/Dq0uVUM5aG

— Vince Langman (@LangmanVince) January 24, 2025

“I was not mad at it, but that is absolutely untrue,” Aniston said, attempting to squash the rumors.

“I’ve met him [Barack] once. I know Michelle more than him.” She explained that their sole interaction happened at a Hollywood gala in 2007—well before his presidency began.

Still, the denials haven’t stopped the rumor mill from spinning.

While Barack has remained silent on both the dating and divorce speculation, Michelle has taken to her podcast at times to voice criticisms of her husband, which some have interpreted as a sign of deep marital strain.

To date, no formal statements have been made confirming or denying the divorce.

But with each new public comment—whether it’s Barack’s unexpected musings on what really matters in a partner, or Michelle’s increasingly candid reflections on life, marriage, and personal growth—the public is left wondering what’s next for America’s former First Couple.

While some hold out hope that their decades-long union will endure, others believe the cracks are already too deep to mend.

For now, all eyes remain on Barack and Michelle, waiting to see whether their story will remain one of resilience—or become one of reinvention.

Connect with Vetted Off-Duty Cops to Instantly Fulfill Your Security Needs

The opinions expressed by contributors and/or content partners are their own and do not necessarily reflect the views of LifeZette. Contact us for guidelines on submitting your own commentary.