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Already late for his hometown wedding, featured troupe dancer and professional gambler John "Lucky" Garnett is delayed further when his fellow dancers, who want to keep him single and in show business, convince him that the cuffless trousers of his morning suit are out of style and need tailoring. By the time Lucky arrives at his fiancée Margaret Watson's home, her infuriated father, Judge Watson, has called off the wedding. Once calm, Watson tells Lucky that, if he wants a second chance with Margaret, he must earn at least $25,000 in New York City. Determined to make good, Lucky accepts Watson's challenge and with his friend, magician Everett "Pop" Cardetti, and his lucky quarter, hops a train to the city. Shortly after they arrive, Lucky, broke but still in his wedding clothes, asks a pretty stranger, Penelope "Penny" Carrol, for change for his lucky quarter so that Pop can buy a pack of vending machine cigarettes. When the machine gives them a flood of unexpected change, Lucky chases after Penny to ask for his quarter back, but she mistakes his eagerness for mashing and refuses his request. After Pop pickpockets the quarter from Penny's purse, Penny accuses Lucky of theft and calls a policeman. To Penny's dismay, the policeman sides with the well-dressed Lucky, and Penny leaves in a huff for her job as an instructor at the Gordon Dancing Academy. Lucky follows Penny into the Academy and poses as an ardent but awkward pupil. Frustrated by Lucky's seemingly hopeless dancing, a still angry Penny insults him in front of Gordon, the Academy's fussy owner, and is fired. To save Penny's job, Lucky insists on demonstrating for Gordon what he has just learned from Penny and executes a complex routine with her. Impressed by the duet, Gordon arranges for Penny and Lucky to audition at the Silver Sandal nightclub but stipulates that Lucky wear a tuxedo in the act. Still broke, Lucky and Pop check into the same hotel as Penny and her older single friend, Mabel Anderson, and try to win a tuxedo from a drunk gambler on the night of the audition. When Penny discovers a half-dressed Lucky playing piquet in his room, she storms away in another huff. A week later, Lucky, who with Pop's help has won hundreds of dollars gambling and has arranged for another audition, finally convinces Penny of his sincerity. However, at the club audition, bandleader Ricardo "Ricky" Romero, who is in love with Penny, jealousy refuses to play for the couple. Lucky then learns that Ricky's contract has been won by Raymond, a casino owner, and with Pop's sleight-of-hand help, wins Ricky's contract for himself. Against his wishes, Ricky plays for Penny and Lucky's triumphant audition, but the dancers' budding romance is stifled when Lucky suddenly remembers his pledge to Margaret. Although he has vowed to stop gambling and has insisted on a modest salary in order to avoid earning the now dreaded $25,000, Lucky instructs Pop to keep him away from the tempting Penny. When Pop reveals to a perplexed Penny the reason behind Lucky's aloofness, Penny again snubs her partner and, in spite of her love for him, returns to Ricky. After Lucky and Penny's grand performance at the Silver Sandal's re-opening, Lucky is surprised by the appearance of Margaret and then is confronted by Raymond, who accuses Pop of cheating him out of Ricky's contract. Raymond demands that the game be re-played with his pack of marked cards, and wins back the contract, after which Penny tells Lucky that she and Ricky are engaged. Thoroughly depressed, Lucky prepares to tell Margaret that he no longer loves her, but she surprises him by revealing that she, too, has fallen in love with someone else. Minutes before Penny is to marry Ricky, Madge tells her about Lucky's broken engagement, while Lucky and Pop conspire to thwart the wedding using the cuffed trouser hoax. In the end, Penny calls off the wedding and reunites with Lucky.