After making a deathbed promise to his mother that he would never marry, Jack Singer (Nicolas Cage) finds that resolve challenged when his girlfriend, Betsy (Sarah Jessica Parker), begins making noise about wanting to start a family. Worried he might lose her, Jack makes the rash decision that they should fly to Las Vegas that weekend to tie the knot. Feet still cold, Jack spurns Betsy's idea to get married the moment they step off the plane, preferring to procrastinate for a few hours over a game of poker arranged by notorious gambler Tommy Korman (James Caan). Peddling the game as a get-to-know-you thrown by the hotel, Korman steadily raises the stakes on Jack until the novice is in for 65,000 dollars of the house's money on a hand he's sure he'll win -- a straight flush to the jack. When he loses the fixed hand, the flabbergasted Jack has a major problem on his hands. Korman offers an unusual solution: If Betsy, whom Korman spotted in the lobby because of her resemblance to his late wife, will spend the weekend with him, Jack's debt will be forgiven. Betsy initially refuses, considering it a ploy by Jack to postpone the wedding, but soon agrees to fly to Hawaii with Korman, in part because it will teach Jack a lesson. When she finds herself charmed by Korman's smooth and sensitive shtick, her desperate fiancé goes to incredible lengths to win her back, including jumping from a plane with a troop of skydiving Elvises.