Heartbreakers (2001 Film) - Plot

Plot

Max (Sigourney Weaver) and Paige Conners (Jennifer Love Hewitt) are a mother-daughter con artist team. When the film opens, the Conners are settling a con on Dean Cumanno (Ray Liotta), an auto-body shop owner and small-time crook. The con, which the Conners have played a number of times before on other men, involves Max marrying Dean, passing out on their wedding night to avoid actually 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 visit the bank to split their earnings, they are 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 together with Max on one last con in Palm Beach (refusing to work anything cheaper as Palm Beach would result in enough money to pay off the I.R.S. and set up Page 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.

Complicating matters is beachfront bartender Jack (Jason Lee), whom Page meets without her mother's knowledge while attempting to go after a target she pointed out earlier (a doctor who inherited money from an uncle; Max rejected him on the grounds that he was a "momma's boy" as he still lived with his mother). Page learns that Jack is worth $3 million, having inherited the bar, and decides to target him for a side con. Page ends up developing genuine feelings for Jack, but Max, who has been hurt many times before, tells her to break it off; Page reluctantly ends the relationship.

Tensy proposes to Max ahead of schedule, but before they can get married, he passes out and dies due to his lifetime of smoking while trying to consummate the marriage. While Max and Page are deciding what to do with the body, Dean arrives, having tracked Max down in order to propose to her again. Dean discovers the ruse Max and Page played on him, and threatens to expose them. Max offers to return Dean's divorce settlement money if he'll help them make Tensy's death look like an accident. Max reveals to Page that the money wasn't really taken by the IRS, and the agent had in fact been Max's mentor, Barbara, in a ruse to prevent Page from leaving. But when Max, Page and Dean go to the bank, the money really has gone, liquidated in an act of betrayal by Barbara.

In order to help Max, Page decides to accept Jack's offer of marriage, planning to work it as a regular con. Page insists that Jack will not cheat on her, but is heartbroken when during the wedding night she breaks into his 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 she drugged him to put him in the position where Page found them, defending her decision by claiming that Jack would have gone on to hurt Page eventually. Dean counters that life is about pain, but that it can also be good, and Max has no right to keep Page from living her life just because of what might happen.

Chastened, Max tells Page the truth, admitting that her own efforts to protect her daughter from pain have only hurt her in other ways, recognising that Page has to make her own life. Page returns to Jack, giving him back the bar he'd had to sell to pay the settlement, and tells him her real name. Max and Dean also get together, Dean having admitted that he still misses Max even after what she put him through. The final shot of the film is of Dean — using the name 'Stanley' — romancing Barbara, with Max watching them via binoculars, implying that Max and Dean are now working together to get Max's money back.