Lucky Jordan is a gangster living in New York City and when he's drafted into the army, he tries to escape duty by using an old con woman named Annie to convince the draft board he's needed at home. When that fails, Jordan is sent to boot camp, but he doesn't stay there long. He takes a beautiful USO worker hostage and flees back to New York. There, he learns that a rival gangster is plotting against America.

A millionaire joins the Navy hoping to find a girl who'll marry him for himself, not for his money. A beautiful gold-digger who works at a resort hotel sets out to get him.

Race horse owner pays so much attention to business he winds up divorced from his wife. His alimony payments are so steep he plots with his lawyer to get her married off.

A ship company employee, Jay Williams, is sent to Florida where one of the company cruise ships is stuck on a reef off of the coast. He obtains waivers from all of the passengers with the exception of Nan Spencer, a department store salesgirl who wants her vacation now, not later. Jay is instructed to take Nan to Havana, set her up in the best hotel, and keep her entertained. She visits a nightclub where the star attraction is Rosita Rivas and meets Rosita's worthless manager, Monte Blanca, who makes a play for her. Trouble also comes in the form of Jay's fiancée, Terry McCracken, when a romance develops between Nan and Jay.