
First Lady Michelle Obama’s First Boyfriend Speaks Out A man named David Upchurch is now telling media sources about his stint as First Lady Michelle Obama’s first boyfriend.
The then 18-year-old Mrs. Obama was escorted by him to her Whitney Young High School prom in Chicago .
They grew up together, were neighbors in the Chi, and David now lives in Colorado Springs , CO . He says the reason they broke up is because he didn’t have his life together and he was “a screw up”. He says: “I always knew Michelle was special and would make a difference in the world.”
I guess the First Lady wasn’t taking any ish even back then. Seven years later she met a law student named Barack Obama. And the rest is history. Love it. 
Cassandra Wilson
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Cassandra Wilson, the two-time Grammy Award-winning jazz singer,
songwriter, and producer, has died. Born December 4, 1955, and died
September 2, 2026, she...
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