New York’s most infamous crap game organizer, Nathan Detroit, hoping for a big pay day, challenges notorious gambler Sky Masterson to a bet he’s sure he’ll win: take mission girl Sarah Brown to dinner in Havana, Cuba. Sky accepts and pursues the known prude, seemingly hopelessly, while Nathan deals with his own situation – his 14-year fiancée, Adelaide, who’s tired of waiting for a wedding. When bets and love seem at odds, the characters are called to question their priorities to make things right.