It was five years ago, in the middle of his meteoric rise through the Chicago improv scene, just before he was ready to move west to pursue his dreams, Warren Cavanee's world suddenly collapsed. His girlfriend Emma, whom he planned to marry, left him and her own pursuit of painting for a more secure lifestyle in the business world of New York. At the same time, his parents announced their divorce, and Warren couldn’t leave his younger brother all by himself in Chicago with the mess. Today, Warren is barely getting by as a barista, slinging coffee to corporate drones and picking up the pieces of his life as his childhood home prepares to be torn down: His father’s vintage Porsche gathers dust in the garage; a symbol of dreams unfulfilled and roads not taken. One fall night, Emma walks into Warren’s coffee shop and back into his life. Although she dreamed of being an artist, Emma is now a hard-working career woman on a stable trajectory, and engaged to Ted Gordon–a successful businessman with all the trappings of what a husband and provider should be. Yet Emma remains ambivalent about her future and the life she really wants. Emma’s return, and Warren's disillusionment at the course she has chosen for her life, inspires him to return to his forgotten passion: the stage. However, as Warren and Emma rekindle their friendship, Warren’s life continues to fall apart. It doesn’t help that his dad, Jack, still lost after the divorce, suddenly loses his job of 35 years, while his mother Claire strikes up a new romance and his younger brother begins to hang with the wrong crowd and slide into a world of drugs. Jack’s mid-life crisis and Warren’s quarter-life crisis collide as Warren struggles to understand his dad’s choices. Warren wants to avoid the mistakes his father made, and decides to take radical action. On the 15th hole of a golf course, Warren finally confronts his father and suddenly, Warren is left facing a decision. Maybe the only thing left to do is take a chance. Maybe the chariot his father never drove off is just waiting for him in the garage. Maybe it's his decision to after all.