About Inspired by Barack and Michelle Obama's first date, SOUTHSIDE WITH YOU recounts the eventful summer day in 1989 when a young law firm associate named Barack Obama (Parker Sawyers) tried to woo lawyer Michelle Robinson (Tika Sumpter) during a daylong date that took them from the Art Institute of Chicago to a screening of Spike Lee's Do the Right Thing to the site of their first kiss outside of an ice cream parlor.