Some time before she was married to former president Barack Obama and served eight years as the first lady of the United States, Michelle Obama enjoyed a more casual romance in her native Chicago with another man. In 2008, Obama’s ex boyfriend, David Upchurch, shared and discussed a prom photo of them with the National Enquirer, a picture which Obama would later post on Instagram in 2020 to encourage high school seniors to vote. Though the couple appeared happy while dressed to the nines in a tuxedo and pink satin dress, their relationship did not persist long after Obama graduated. As the first of Obama’s ex-boyfriends to discuss their relationship, Upchurch revealed their relationship was happy, albeit short-lived.
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Upchurch and Obama, then Robinson, started dating in the early 1980s, while the unknowing first lady-to-be was still a junior in high school. Upchurch told the National Enquirer that he and Obama had grown up together as neighbors and family friends in Chicago. They spent approximately a year and a half together, and even attended the Whitney M. Young High School’s prom in 1982, a night which Upchurch has since claimed he’s forgotten in detail. While sparks may have flown between Obama and Upchurch while the latter was still a high schooler, their differing priorities entering adulthood eventually led to their romance’s downfall. “Michelle knew what she wanted and after graduation she was off to Princeton University,” he told the National Enquirer (per Daily Mail). “I couldn’t stand in her way.”
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David Upchurch blames himself for his relationship with Michelle Obama ending
Michelle Obama’s ex boyfriend David Upchurch said their relationship ended due to a lack of responsibility on his part. “Michelle and I really liked each other, but you know how some high school boys are,” Upchurch told the National Enquirer. “We’re not ready to be responsible and we screw up. I was a screw-up, plain and simple. At that point, I just didn’t take my life or my future seriously.” Conversely, Obama simply stated in her 2018 memoir “Becoming” that she left Upchurch behind upon entering university life.
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While Upchurch was still figuring out where his life was heading, Obama was preparing for her future at Princeton, where she went on to earn her B.A. in sociology in 1985. Though her romance with Upchurch was cut short, her ex-boyfriend has wished Obama the best, having said he is proud of her stunning transformation since their high school days. “I always knew Michelle was special and would make a difference in the world,” he told the Enquirer. Considering people now refer to Barack Obama as “Michelle’s husband,” it says something that she’s able to outshine her presidential spouse.
