In a smoky dive bar, two weary, enigmatic friends, and a jaded, cynical barmaid cling to the end of the night, not yet ready for home. Faced with empty glasses and empty pockets, the friends propose a little competition: whoever can tell the saddest story wins a drink on the house. The barmaid shrugs her vague consent - anything to pass the time. However, as the stories unfold and the tragic tales unravel, what started as idle fun turns into a dark night of personal revelation, as all three characters come to terms with the crooked twists and turns that have led them to their desperate position in life.