After losing $65,000 to professional gambler and con man Tommy Korman (James Caan), penniless private investigator Jack Singer (Nicolas Cage) agrees to let Korman borrow his beautiful fiancée, Betsy (Sarah Jessica Parker), for a Hawaiian getaway to pay off his debts. But when Betsy -- who looks just like Korman's late wife -- begins to fall for her charismatic captor, the commitment-phobic Singer must race against the clock to track them down and win her back.