Chronicles a single day in the summer of 1989 when the future president of the United States, Barack Obama, wooed his future First Lady on an epic first date across Chicago's South Side.
| Actor | Role |
|---|---|
 Parker SawyersBarack Obama | Barack Obama |
 Tika SumpterMichelle Robinson | Michelle Robinson |
 Vanessa Bell CallowayMarian Robinson | Marian Robinson |
 Phillip Edward Van LearFraser C. Robinson | Fraser C. Robinson |
 Deanna Reed-FosterBernadette | Bernadette |
 Jerod HaynesTommy | Tommy |
| GGabrielle Lott-RogersRafiqa | Rafiqa |
 Taylar FondrenJanice | Janice |
 Donn C. HarperCurtis | Curtis |
| PPreston Tate Jr.Kyle | Kyle |
| FFred Nance Jr.Nance Residence | Nance Residence |
 Donald PaulBow Tie | Bow Tie |
 Jeremy Michael PereiraBar Patron | Bar Patron |