According to Michelle Obama, the date included lunch at the Art Institute of Chicago and a "kinda romantic" walk down Michigan Avenue.
"Art. Guys out there--it impresses people," Obama offers in the video.
They also went to see Spike Lee's "Do the Right Thing," a 1989 film about racial tensions in a Brooklyn neighborhood.
"He showed all the signs," the first lady said. "He was hip, cutting-edge, cultural, sensitive.”
The "First Couple" video promotes the Obama campaign's "Dinner with Barack and Michelle" fundraising opportunity, in which supporters can enter a raffle to join the Obamas on their next date night.
As for Obama's campaign rival, Mitt Romney, he first fell in love with wife Ann at her 16th birthday party, according to a Romney campaign video released for their 43rd wedding anniversary.