Michelle Obama’s brother, Craig Robinson, recently shared that he once had doubts about her relationship with Barack Obama, her husband and the 44th President of the United States.
Michelle and Barack first met in 1988 while working at a law firm in Chicago, where Michelle had been assigned as Barack’s adviser. They married four years later and went on to have two daughters—Malia, born in 1998, and Natasha (Sasha), born in 2001.
In 2009, Barack made history as the first Black President of the United States, serving two terms until 2017. He has since acknowledged that the demands of the presidency placed a strain on their marriage.
Speaking on the Michelle Obama: The Light Podcast—which aired Wednesday, April 16—Craig Robinson opened up about his early impressions of Barack and why he was initially skeptical about their long-term future together.
Former First Lady Michelle Obama delivers remarks alongside former US President Barack Obama at a ceremony to unveil the official Obama White House portraits at the White House (Kevin Dietsch/Getty Images)
He said: “So Mich starts to date Barack, and we don’t know who this guy is. We’re just like, ‘Barack? Who’s got a name like Barack?’”
Craig admitted he didn’t think the relationship would go far. “I’m thinking it’s gonna last a month, like most of your relationships,” he joked.
Michelle, now 61, playfully pushed back at her 62-year-old brother’s comment, quipping, “That’s not true. I’ve had many a long-term boyfriend.”
Craig shot back with a laugh, “I wouldn’t call those guys boyfriends.”
Reflecting on the first time Michelle brought Barack home, Craig added, “I remember Mom’s first thing was, ‘Oh, at least he’s tall!’ That was her first reaction, because Mich was usually posting up her other boyfriends.”
He then confessed, “And I said to myself, ‘Too bad it’s not going to last.’”

Michelle Obama and Craig Robinson speak on stage during a live IMO podcast episode, in Texas last month (Marcus Ingram/Getty Images)
However, their relationship certainly has and it shows no sign of slowing despite divorce rumors – which Michelle addressed last week.
While appearing as a guest on Sophia Bush’s Work in Progress podcast, Michelle Obama opened up about the freedom she’s felt since leaving the White House and stepping away from the role of First Lady—particularly when it comes to making decisions for herself.
“For the first time, I’ve been able to make choices just for me,” she shared. “The interesting thing is that when I say ‘no,’ for the most part, people are like, ‘I get it,’ and I’m okay.”
Michelle reflected on the pressure women often feel to meet others’ expectations. “That’s the thing we as women struggle with—disappointing people,” she said.
She went on to address the rumors surrounding her marriage to Barack, attributing them to society’s discomfort with women exercising autonomy. “People couldn’t even fathom that I was making a choice for myself, so they had to assume that my husband and I were divorcing,” she explained.
The former First Lady pointed out that the speculation came from a deeper societal issue: “It couldn’t just be a grown woman making a set of decisions for herself. That’s what society does to us. And if it doesn’t fit into the stereotype of what people think we should do, then it gets labeled as something negative and horrible.”