Guy and Madeline on a Park Bench is about the often uneasy but always beautiful relationship between music and love. It tells the story of a young Boston jazz musician who drifts from affair to affair, his trumpet the only constant in his life. He makes a promising connection with an aimless introvert named Madeline, who immediately takes to his music. Their relationship is cut short, however, when Guy leaves her for another, more outgoing love interest. The two separated lovers slowly wind their way back into each other’s lives, through a series of romances and near-romances punctuated by song.