Not Tonight Josephine is a historical trivia game. The game includes glass bead gaming pieces, a colorful board and question cards, many of which are also in color. There are two boxes for the cards, and cardboard coins, as well as dice. There are 30 different question categories on the board, which uses a circular track with a hub layout. The question categories some are more traditional like "Ancient History", "Royalty" and "American Civil War", others are of a quirky nature such as "Famous Exits", "Cockney English" and "Submarines". Players draw a card which will have a choice between two categories from which to answer, all questions are multiple choice with three possible answers. If the player gets a question right they can roll again, if the question is the same category as the space the player is on they also receive a coin. The four special Double Trouble space on the board give the player a coin if they can answer both questions on the card. The player with five coins who then returns to the center of the board wins the game.