Before pagers and cell phones, and before Facebook and YouTube even existed, five strangers in Chicago meet in a car on the ride of their life. Vi is a songwriter on the verge of moving to Nashville, and Tom is her silent admirer. Sean is a drunken Irish boy ogling every skirt in the bar, and Sarah is a young, rich socialite trying to avoid Sean's gaze. The four strangers leave Baker's Tap in William's Towncar, caught up in his weekly superstitious quest for purchasing lottery tickets at an old country diner.On their journey, Tom will try to stop Sean from making obnoxious passes at Sarah while he keeps one eye on Vi. Vi will try not to think of Tom romantically because she has her future planned out and no one can stop her quest as a singer. Sarah will try to stay aloof to everyone beneath her, and William will try to get to the diner by midnight so that he can buy his lottery tickets in time. Between arguments and revelations, each of their stories will connect as they privately sort out their pasts. Each of their defenses are lowered long enough for introspection, and if they are lucky, a future that includes a jackpot.