In New York, the smalltime gambler Nathan Detroit has been eloping from getting married with his girlfriend Adelaide for fourteen years. Nathan needs one thousand dollars in advance to rent a place for the crap game but neither he nor his friends Nicely-Nicely Johnson and Benny Southstreet can afford. Nathan decides to bet against the gambler Sky Masterson, challenging him to have a dinner in Havana with a woman of his choice. Sky accepts the bet and Nathan chooses the prude Sergeant Sarah Brown, who runs a mission for sinners. Sky visits Sarah and invites her to have dinner with him in Havana; in return, he would bring one dozen sinners to the mission. Sarah refuses the deal, but when General Cartwright comes to New York to shutdown the mission, Sarah feels that the only chance to keep the mission operating is accepting Sky's invitation. They travel to Havana and fall in love with each other; but when they return to the mission, Sarah discovers that Nathan used the place for his crap game. Further, she believes that Sky has plotted the scheme to use her. Now Sky has to convince the gamblers and gangsters that arrived in New York to the crap game that they should go to the mission to help Sarah.
