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.

A small circle of friends suffering from post-collegiate blues must confront the hard truth about life, love and the pursuit of gainful employment. As they struggle to map out survival guides for the future, the Gen-X quartet soon begins to realize that reality isn’t all it’s cracked up to be.