Michelle Obama Reflects on Unconventional Love and Why Michelle Obama Tried to Set Barack Up with Her Girlfriends at First
- Victor Nwoko
- May 1
- 2 min read
Former First Lady Michelle Obama opened up about her unexpected path to love and partnership with former U.S. President Barack Obama, calling their relationship “the ultimate swerve” during a podcast interview released on May 1. Speaking alongside her brother Craig Robinson, Michelle shared candid reflections on her personal growth, early career, marriage, and the power of resilience.
Michelle described herself as a “box checker,” someone who focused on doing what was expected of her, including attending Ivy League schools and securing a prestigious job at the Sidley & Austin law firm in Chicago. It was there she met Barack Obama, who she was assigned to mentor. She recounted that Barack made an unorthodox first impression—arriving late to their first meeting—but quickly captivated her with his intelligence and charm. “He did nothing by the book. He was brilliant and interesting,” Michelle said, noting that despite being annoyed initially, she found him more attractive than his photos and realized they had an immediate connection.
While the two clicked as friends, Michelle initially resisted a romantic relationship. She even attempted to introduce Barack to her girlfriends, thinking it would appear unprofessional or predictable for two Black associates at the same firm to date. “I was into doing what wasn’t expected,” she recalled. But Barack was undeterred, famously telling her, “Who cares what it looks like,” before asking her out.
Their first date included a trip to an art institute, a stroll down Chicago’s Michigan Avenue, dinner overlooking the city, and a screening of Spike Lee’s Do the Right Thing. That experience marked a turning point for Michelle. “I started swerving,” she said, embracing a new direction in life that ultimately led to a lifelong partnership.
Michelle acknowledged that their relationship has not been without challenges. She spoke openly about the realities of marriage, pushing back on public perceptions of perfection. “People give up too quickly on marriage,” she said. “There is so much friction built into the equation.” While she admitted there were times of resentment, anger, and feeling overlooked, she emphasized that she never seriously considered leaving the marriage. “The beauty of my husband and our partnership is that neither one of us was ever really going to quit at it,” she added.
Craig Robinson shared that he was initially skeptical of Barack, estimating their relationship might last only a couple of months. Their mother, Marian Robinson, had once simply commented, “at least he’s tall,” upon meeting Barack. Michelle noted that she had dated others in the past but had only brought one other boyfriend home before Barack.
Reflecting on Barack’s presidential run in 2008, Michelle said she fully believed in his potential. “I knew he had it in him to make this happen. He would make a phenomenal president,” she stated.
Responding to ongoing rumors about marital discord, Michelle dismissed them firmly. “If I were having problems with my husband, everybody would know it,” she said. “I’m not a martyr. I would be problem solving in public.”
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