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The story, inspired by anecdotes chronicled in the memoirs of their actual first date, begins in August, 1989, in the South Side of Chicago, on a day in which a young, smart and career-minded corporate lawyer, Michelle Robinson, accepts spending the day with a Harvard-bound summer office mate, Barack Obama, on the pretense that they attend a housing project community meeting as colleagues, making whatever else they do socially that he has planned definitely not a date. Obama, driving his rusted-out car to greet her, feels differently, and makes it his task to convince her otherwise before the day is through.