Max (Sigourney Weaver) and Page (Jennifer Love Hewitt) are a brilliant mother and daughter con team who have their gift down to a fine art. Max targets wealthy, willing men who fall prey to her beauty and charm, and marries them. The equally gorgeous Page then seduces them. Max "catches" her wayward husbands in the act and then it's off to arrange a big fat cheque to settle the alimony payment and on to the next victim, with Max and Page posing in a variety of deceptive guises to keep one (or two) steps ahead of the law.

Heading for Florida, Max and Page set their sights on their greatest targets: William B. Tensy (Gene Hackman) of Tensy Tabacco, a billionaire with a world-class, record-shattering cough resulting from years of smoking his own cigarettes; and the decent Jack (Jason Lee), seemingly a bartender of modest means. Complications soon arise, professionally and personally. While Max ties to take Tensy for the ride of his quickly dwindling life, her last victim of marital deceit, a very angry but still heavily-in-lust mafia-type named Dean (Ray Liotta), is hot on her tail. And to the surprise of tough-as-nails Page, Jack finds a chink in her emothional armor and she begins to realize that even breakers of hearts can sometimes have their hearts broken.