Max and Page Conners (Sigourney Weaver and Jennifer Love Hewitt) are a mother-daughter con artist team. When the film opens, the Conners are finishing a con on Dean Cumanno (Ray Liotta), an auto-body shop owner and small-time crook. The con, which the Conners have played many times before on other men, involves Max marrying Dean, passing out on their wedding night to avoid consummating the marriage, and then Page (posing as Dean’s secretary) luring Dean into a compromising position to justify Max’s immediate divorce and hefty settlement. The con is a success.
Page declares that she wants to go solo. Max initially relents, but when they go to the bank to split their earnings, they’re confronted by an IRS agent (Anne Bancroft) who declares that they owe the government a considerable sum on top of the rest of their savings, which have already been seized. Page reluctantly agrees to work one last con with Max in Palm Beach, to get enough money to pay off the IRS and set Page up to work on her own. For their target, they choose widower William B. Tensy (Gene Hackman), a tobacco baron who is addicted to his own product.
While working the main con with Tensy, Page attempts a side con without her mother’s knowledge. Page targets beachfront bartender Jack (Jason Lee), who is worth $3 million; she tells him that her name is Jane, but develops genuine feelings for him. Max learns of the side con and tells Page to break the relationship off, which Page does reluctantly.
Tensy proposes to Max ahead of schedule, but before they can get married, he accidentally chokes and dies while trying to initiate sex with Max. While Max and Page are deciding what to do with the body, Dean arrives, having tracked Max down to apologize and propose to her again. Dean figures out that Max and Page conned him, and threatens to call the authorities. Max offers to return Dean’s divorce settlement money if he’ll help them make Tensy’s death look like an accident. Max tells Page that their money wasn’t really taken by the IRS; the agent was Max’s mentor, Barbara, who agreed to help prevent Page from leaving. However, when Max, Page and Dean go to the bank, the money really has gone, having been liquidated in an act of betrayal by Barbara.
In order to help Max, Page returns to Jack and accepts his proposal, planning to work it as a regular con. Page insists that Jack will not cheat on her, but is heartbroken when, on their wedding night, she breaks into her mother’s room and finds him in a compromising position with Max. After the divorce settlement is paid, Dean confronts Max about the ethics of their con, pointing out that even a “goody-goody” like Jack is only human. Max reveals that Jack actually turned her down and that she had to drug him, but she defends her actions by saying that Jack would hurt Page eventually. Dean counters that Max has no right to keep Page from the man she loves because of what “might” happen.