In a recent episode of their IMO podcast, Michelle Obama and her brother Craig Robinson took a nostalgic look back at the early days of her relationship with Barack Obama, revealing some surprising first impressions.
Joined by actress Tracee Ellis Ross for a discussion about dating, Michelle opened the episode with a laugh. “I love talking about dating because I haven’t done it in decades,” she joked, according to DailyMail.com.
Craig Robinson shared that when Michelle first introduced Barack to the family, he wasn’t convinced their relationship would last. “We don’t know who this guy is, we’re just like, ‘Barack? Who’s got a name like Barack?’ And I’m thinking it’s gonna last a month like most of your relationships,” Robinson said playfully.
Michelle quickly objected. “That’s not true. I’ve had many a long-term boyfriend,” she replied, prompting Craig to tease, “I wouldn’t call those guys boyfriends.”
Craig recounted how their late mother, Marian Robinson, was immediately pleased when she met Barack, simply because he was tall. However, Craig remained skeptical. “I said to myself, ‘Too bad it’s not going to last,’” he admitted.
At Michelle’s request, Craig agreed to take Barack out for a game of pick-up basketball — a test of character passed down from their father, who believed you could learn a lot about a person through how they played the game. Though initially reluctant to “do her dirty work,” Craig agreed and reported that they had a great time playing, and that Barack handled himself well both on and off the court.
Despite the humorous doubts early on, Michelle and Barack would go on to build a life together, withstanding years in the public eye and the pressures of political life.
Their conversation arrives as rumors swirl about the couple’s relationship, intensified by Michelle’s recent absences from major public events. However, both Michelle and Barack have spoken candidly about the challenges and realities of maintaining a relationship under the intense pressures of public life.
In a conversation at Hamilton College, Barack acknowledged that there were periods when he struggled to balance the demands of his presidency with his family life. “I was in a deep deficit with my wife,” he admitted. “So I have been trying to dig myself out of that hole by doing occasionally fun things.”
Michelle has also addressed speculation about her marriage, firmly stating that her personal decisions to scale back public appearances are about prioritizing her own well-being, not signs of marital troubles.
Speaking on Sophia Bush’s Work in Progress podcast, Michelle explained, “That’s the thing that we as women, I think we struggle with — disappointing people.” She emphasized that choosing herself was a natural, healthy decision, and criticized the tendency to assume that women’s personal choices must be tied to relationship issues.
“People couldn’t even fathom that I was making a choice for myself,” she said. “It had to be assumed that my husband and I are divorcing. That this couldn’t be a grown woman just making decisions for herself, right?”
Michelle further reflected on the societal expectations placed on women and the importance of living authentically. “Now is the time for me to start asking myself these hard questions of who do I truly want to be every day,” she said. “And that looks like whatever I want it to look like.”
While public speculation continues, both Michelle and Barack have been open about the normal ups and downs of a long relationship, offering a candid glimpse into what it means to nurture a marriage amid extraordinary pressures.
Their reflections remind many that relationships — even between two of the world’s most recognizable figures — are built on patience, effort, and understanding.