The film portrays an evening in the life of Eddie, a writer, seeking a second chance with an ex-girlfriend, the love of his life, Nina. Meanwhile, his friend Max, an artist and musician, is hoping to start a new romance on a blind date with Veronica. The couples wander through the city of Chicago determined to see the sunrise together. Despite their efforts to appear confident and successful, it is only a matter of time before the truth of how lost they all are in life makes its way to the surface. Whether Eddie and Nina can reconnect despite their rocky past or Max and Veronica can connect for a happy future reveals itself as the sun rises.