08/08/2026
The summer of 1989 was unseasonably hot in Chicago, and inside the corporate walls of Sidley & Austin, a young Harvard Law student named Barack Obama was about to meet the woman who would change his life. He had arrived as a summer associate, his photograph in the firm directory so unflattering that Michelle Robinson later admitted she was "pleasantly surprised to see that my nose and ears weren't quite as enormous as they looked in the photo". Assigned to mentor him, the 25-year-old associate found his advances "completely tacky" and initially refused his date requests. But Barack was persistent, finally convincing her to go out with him by offering to quit his job. On July 1, 1989, their first date began with lunch at the Art Institute of Chicago, a stroll down Michigan Avenue, and a screening of Spike Lee's "Do the Right Thing." By the end, Michelle later recalled, "We clicked right away… I was sold." The night concluded at a Baskin-Robbins on 53rd Street in Hyde Park, where the young couple sat on the curb with their ice cream. As Barack leaned in for a kiss, he later recalled, "I kissed her, and it tasted like chocolate". That sweet moment on the sidewalk was the beginning of a lifelong partnership. Two years later, on July 31, 1991, Barack passed the bar exam and took Michelle to their favorite downtown restaurant, Gordon's, to celebrate. As they reached the end of the meal, Barack once again raised the subject of marriage, a topic that had always frustrated Michelle. She felt the blood rise in her cheeks, believing they were about to have another argument. But then the waiter arrived with a dessert tray, and instead of chocolate cake, a diamond ring sat in a velvet box. Barack dropped to one knee, and the entire restaurant erupted in applause. On October 3, 1992, Barack and Michelle Robinson were married at Trinity United Church of Christ in Chicago. Michelle's brother walked her down the aisle, while Barack's brother stood as his best man. Stevie Wonder's "You and I" played as they shared their first dance, and a new chapter in American history began.