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The first boyfriend of Michelle Obama has provided new insights into the First Lady, not to mention a prom night photograph of her in a satin dress with plunging neckline and a high slit.

Michelle Obama’s high school prom date reveals that his romance with the future first lady went nowhere because, “I was a screw-up, plain and simple!”

5 love lessons from the Obamas.

Back in 1982, David Upchurch escorted then 18-year-old Michelle Robinson to her prom at Whitney M. Young High School in Chicago. Upchurch is now a customer service representative and divorced father of three living in a modest house in Colorado Springs.

He claimed he had “pretty much forgotten” their prom date together and couldn’t even recall if it ended with a kiss.

Michelle met Barack Obama when she was a 25-year-old lawyer at a corporate law firm, having just left Harvard Law School.

What would your first boyfriend say about you?  Tell us in comments!

Michelle Obama tells Barack to stay out of her closet.

For 2024’s iteration of MadameNoire and HelloBeautiful’s annual series Women to Know, we knew we wanted to celebrate the people who help make the joys of film and television possible. To create art is to create magic. This year, we spotlight Hollywood Executive’s changing the face of cinema.