Plot

Jack loses $65,000 in poker in Las Vegas, where he's marrying Betsy. The wedding will have to wait as the poker winner wants the weekend with Betsy to cancel the debt. She accepts. Whom will she marry?

On her deathbed, a mother makes her son promise never to get married, which scars him with psychological blocks to a commitment with his girlfriend. They finally decide to tie the knot in Vegas, but a wealthy gambler arranges for the man to lose sixty-five thousand dollars in a poker game, and offers to clear the debt for a weekend with his fiancée. Suddenly the man is insanely jealous, and pursues his fiancée and her rich companion, but finds pitfalls in his path as the gambler tries to delay his interference.—Ed Sutton <esutton@mindspring.com>

Commitment-phobe Jack loses a big fortune in Vegas to a professional gambler, who borrows Jack's fiancee Betsy for a getaway as collateral. But when Betsy starts falling in love with her captor, Jack must summon his courage to win her back.—Anonymous

In 1985, Jack Singer (Nicholas Cage) swears to his overbearing and possessive mother, Bea (Anne Bancroft), while she is on her deathbed, that he would never get married because Bea is the only woman who will ever love Jack.

Over the next seven years, Jack, who works as a New York private detective that handles divorce cases, begins dating Betsy (Sarah Jessica Parker), an elementary school teacher, but is reluctant to commit. By the present day in 1992, Betsy finally tires of Jack's reluctance and threatens to leave him. Fearful of losing her, Jack suggests a spontaneous trip to get married in Las Vegas, Nevada. They check into the Bally's Hotel during a convention of Elvis Presley impersonators.

Before the wedding, however, a high-stakes gambler named Tommy Korman (James Caan) sees Betsy from a distance in the hotel lobby and notices a striking resemblance to his beloved late wife Donna. Tommy, an eternal and ruthless romantic, determines to romance Betsy and marry her. Jack is very nervous about getting married and decides to relax by gambling first. Tommy lures him into a high-stakes poker game.

Up in Tommy's hotel suite, he arranges a crooked poker game (with Jerry Tarkanian as one of the other players) where Jack borrows $65,000 after being dealt a straight flush (7-8-9-10-Jack of clubs), only to lose to the gambler's higher straight flush (8-9-10-Jack-Queen of hearts); Tommy, however, promises to erase the debt with a proposal: Tommy offers to accept a platonic weekend with Betsy as payment for the debt, and Jack reluctantly agrees. Betsy is furious when Jack tells her about his predicament, but Tommy charms her and she agrees to the arrangement. Tommy Korman meets Betsy for drinks and reveals they will be spending the weekend at his beachfront estate in Kauai, Hawaii. As Betsy packs for the trip, Jack realizes the magnitude of his mistake, and asks her to marry him immediately. However, Betsy does not believe his proposal is sincere, or he would have married her upon their arrival in Vegas. She plans to honor the deal with Tommy, and informs Jack that they will return from Hawaii mid-week. Tommy flies with Betsy to his estate, where she meets his family and is impressed by his thoughtfulness. Upset, Jack returns home to New York to wait.

One of Jack's clients, an emotionally erratic man named Sydney Tomashefsky (Robert Costanzo) tells Jack about his crazy suspicions about his wife cheating on him with boxer Mike Tyson.

Meanwhile, Tommy continues to court Betsy at his island paradise house, trying to woo her to replace his late wife whom he confides in her about.

Jack becomes more agitated when he sees a television news story about a volcano erupting in Hawaii, and spots Betsy and Tommy among the excited onlookers. Jack flies to Hawaii, but his efforts to see Betsy are thwarted by Tommy's men.

When Tommy learns that Jack has left New York and is heading to Hawaii to try to get Betsy back, the gambler hires a local taxi driver friend, named Mahi Mahi (Pat Morita) to keep Jack as far away as possible from him and Betsy until he manages to persuade her to marry him.

When Jack arrives on Kauai, Mahi Mahi intercepts him and takes Jack on an aimless drive around the island, leading them to an old Hawaiian chief's house who is Chief Orman (Peter Boyle), where Mahi Mahi tries to stall Jack.

At the same time, Tommy begins feeding Betsy lies about Jack, first claiming that Jack lied to her about the gambling bet by claiming that Jack only lost $3,000 instead of $65,000 and that Jack has used Betsy as collateral, which makes Betsy feel more hurt and betrayed. He tries to calm her down by proposing marriage. Believing Tommy's lies, Betsy accepts his proposal. He insists they return to Las Vegas and get married immediately.

At Chief Orman's house, Jack eventually figures out that Mahi Mahi must be on Tommy's payroll, so he distracts Mahi Mahi for a minute where Jack steals the taxi and drives off looking for Tommy and Betsy. After learning from Tommy's son and wife that Tommy hangs out at the Kauai Club, Jack drives over there that evening, and sees Betsy outside the club. But before Jack can approach her, he is attacked by Tommy and arrested.

Jack calls his bookie dentist friend Dr. Molar (John Capodice) in New York who pays for Jack's $5,000 bail. Mahi Mahi meets him outside and admits that Tommy Korman left for Vegas with Betsy and has convinced her to marry him. Mahi races Jack to the airport.

As Betsy and Tommy arrive back in Las Vegas, she tries to contact Jack to inform him about her choice, but cannot reach him anywhere. This slowly leads her to have second thoughts about marrying Tommy.

Meanwhile, Jack cannot get a connecting flight to Las Vegas and ends up in San Jose, California where another one of Tommy's employees (a ticket agent) tries to stall Jack again from getting a flight to Las Vegas. Jack tries frantically to find a flight to Vegas. Finally, he finds a group about to depart for Vegas, but, much to his surprise, finds out mid-flight that they are the Utah chapter of the "Flying Elvises" - a skydiving team of Elvis impersonators led by the flamboyant Roy Bacon (Burton Gillam). Jack now realizes that he will have to skydive from 3,000 feet in order to get to Betsy.

Back in Las Vegas, Tommy tries to rush Betsy to a wedding chapel, but she hesitates and asks to wait a few weeks. Tommy, sensing that he is losing control of the situation, offers her $1 million to marry him right away. She is disgusted by the offer and starts to leave. However, Tommy snaps and threatens that she agreed to the marriage... and no one breaks their word to him. Intimidated (and finally seeing the gangster that Tommy really is), Betsy asks to use the ladies room before leaving for the wedding chapel. As Tommy waits, Betsy follows several showgirls to their dressing area, dons a showgirl's costume, and sneaks out of the hotel. As Tommy and his men search for Betsy, she hides among the crowds lining the street to see the arrival of The Flying Elvises.

Although Jack is afraid of dying, his love for Betsy overcomes his fear, and he jumps out of the plane with the other skydivers. Betsy hears Jack's name announced as he lands, and she runs into his arms. He declares his love, and asks her to marry him. From a short distance away, Tommy sees the couple together and realizes he has lost Betsy. Tommy tells his henchmen to let Jack and Betsy go and then heads back inside the hotel to his suite to set up another poker game with some of the guests. (Note: even though Tommy is the villain of this film, one can't help it but feel a tiny bit sorry for him.)

The final scene shows Jack and Betsy getting married in a small Las Vegas chapel with the Flying Elvises as guests, Jack still in his white illuminated jumpsuit and Betsy in her stolen showgirl outfit.