In a bustling fictionalized Manhattan, Nathan Detroit challenges high-rolling Sky Masterson to a bet: Sky must take a woman of Nathan’s choosing on a dinner date to Havana, Cuba. Nathan and Sky embark on parallel romantic journeys with Nathan’s fiancé Adalaide and Sky’s target, the pious missionary Sarah Brown. As Sky falls for Sarah Brown and Nathan’s love for Adalaide burns anew, the two men discover what a guy must do to win over the woman he loves.