Inspired by Barack and Michelle Obama's first date, SOUTHSIDE WITH YOU recounts the eventful summer day in 1989 when a charming young law associate named Barack Obama (Parker Sawyers) tries to woo reluctant attorney Michelle Robinson (Tika Sumpter) during a daylong date that takes them from an art exhibit to a screening of Spike Lee's DO THE RIGHT THING to a sweet first kiss outside of a Baskin-Robbins ice cream parlor.