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 past. Vi likes Tom, she finds herself interested in him, and she has noticed him in the audience for weeks, but she is ready to move to Nashville to continue her singing career, and she doesn't have time for a relationship. Tom is disconnected after a lifetime of abuse and running from his past, and Vi might be the only person who can break down his wall. Sean is looking for his next drunken party and for Sarah to say yes, or for any girl to say yes, but Sarah won't have anything to do with him. Sarah is preoccupied, having been stranded at the bar by her boyfriend. She was raised in the wealthy north suburbs of Chicago, and she can't help but look down on the others. She spends the night trying to reconcile her self-image, trying to ignore her bulimia, and trying to escape the food that comes into her view. And William just wants a quiet life and his lottery tickets, but the four others in his car will disrupt his habitual weekly trip.
Each of their defenses are lowered long enough for introspection, and if they are lucky, a future that includes a jackpot.