Michelle Obama’s brother, Craig Robinson, once doubted the longevity of her relationship with Barack Obama. In a candid conversation on their podcast IMO with Michelle Obama & Craig Robinson, Craig admitted that when Michelle began dating Barack, he thought it would last only a month. He humorously remarked, “We don’t know who this guy is. We’re just like, ‘Barack? Who’s got a name like Barack?’” However, Michelle quickly defended her past relationships, stating, “I’ve had many a long-term boyfriend.” Craig jested, “I wouldn’t call those guys boyfriends.”

The siblings also reminisced about their first meeting with Barack. Their late mother, Marian Robinson, was impressed by his height, but Craig was initially skeptical. Michelle then asked Craig to take Barack to play basketball—a test Craig was reluctant to undertake. Eventually, he agreed, and after the game, he acknowledged that Barack had “done fine.”

Despite early doubts, the Obamas’ relationship has flourished. In October 2025, they celebrated their 33rd wedding anniversary. Michelle expressed her enduring love for Barack, calling herself “lucky to go through life” with him, while Barack described marrying Michelle as the “best decision” of his life.

In their podcast, Michelle and Craig discuss various topics, including relationships and personal growth. Michelle has addressed rumors about her marriage, emphasizing that her recent decisions to step back from certain public commitments are about prioritizing herself, not marital discord.