The movie opens with Sigourney Weaver getting married to Ray Liota. The wedding night comes and Sigourney falls asleep before the two can have sex. Ray wakes up and goes to work where his secretary (Jennifer Love Hewitt) is waiting in a tight dress. He cannot overcome his urges and starts making out with Jeniffer. Sigourney walks in and catches them in the act. She files for divorce and takes half of his money and a car.
We then find out that Jennifer and Sigourney are a mother daughter duo of con artists who marry men and then set them up to cheat so that they can take half of the husbands property.
The two women have various ways of getting things for free throughout the whole movie; putting broken glass into their meal, slip on a puddle of goo that they put there, in order to get a hotel room.
After the divorce from Liotta, Jennifer decides that she is a PRO, and can handle herself on her own.
Sigourney needs to convice her to stay so she comes up with a plan. When the duo go to the bank to withdraw their money they are told that Sigourney has no money in her account. Sigourney had given her friend, an IRS agent her account number and had the agent hold all her money so it appeared she was broke. Sigourney convinces Jennifer to do one last con.
The women drive along the beach in a speedboat looking at possible people to con. Jennifer has her eyes set on a young mamas boy while Sigourney sees an old single man (Gene Hackman) who is a chain smoker and coughs every 3 seconds. The two decide to go with Gene Hackman, while Jennifer is not to sure.
Sigourney moves in on Gene at an auction, while Jennifer is at a bar, owned by Jason Lee. He approaches Jennifer and asks her what she wanted to drink. Jennifer thought this was a pick up line and freaked out at him. While Jason comes back with a drink, Jennifer gets a phone call from her mother.
Jennifer storms out of the bar and goes to the spot her mother told her and lays out a spike strip in the road so Gene Hackman would get into a car accident. Little did she know that she left her purse at the bar and Jason Lee was returning it. He runs over the spike strip and crashes into a tree. The two have an awkward moment when Jennifer sees Gene coming and pushes Jason Lee down a hill so he does not see the spike strip in the road. The two fall down while Gene crashes into Jasons car. Jennifer then makes out with Jason to keep him distracted while Sigourney convinces Gene that she will take him home.
Once home Sigourney has an encounter with the housekeeper of Genes home. It turns out that the housekeeper is on to Sigurneys plan. Jennifer goes into the maids room and sets her up by making it appear she stole all of Genes ex-wifes jewelry. The maid goes to jail and Jennifer becomes the new housekeeper.
After a night out on the town, Gene Hackman comes to Sigourneys house and asks her to marry him. Along with him he brought a statue that Sigourney bought at the auction where they met but broke the penis off (it was a statue of a naked man) . Gene brought it back penis and all. After Gene asks her to marry him, he goes to kiss her and trips and hits his head on the penis of the statue and dies.
Ray Liotta then shows up and asks Sigourney to marry him because he messed up and he hasnt forgotten about what they had and he wants another chance. Jennifer Love Hewitt walks in and Liotta realizes he was "played" by the two women. He demands his money back but they don't have any. They decide if he helps them put Hackman's body back to his own house they would include him in the next con.
Jennifer Love Hewitt goes pack to the bartender and he eventually asks her to marry him. She has a few doubts but with Sigourney and Liotta posing as her second cousins, she eventually agrees. On their wedding night, they pull the same routine with them about to have sex and Jennifer fallls asleep. When he realizes she's asleep, he leaves the room. Jennifer opens her eyes and is crying. She actually loves him.
Outside, Sigourney meets up with him and invites him to her house for a drink. She keeps trying to seduces him but he won't bite. Finally, Jennifer Love Hewitt comes over (as planned) and sees him asleep in Sigourney's bed.
The next scene is in the divorce court and Jason Lee decides to give her whatever she wants.
As they're driving home Sigourney tells Jennifer that he didn't want to sleep with her, she actually had to drug him to get him in bed.
Jennifer realizes that Jason really did love her.
Jason is heads back to the bar and his friend tells him he forgot a few things (after selling the bar to pay off the divorce). When he opens the door, it shows everyone welcoming him back. It was a surprise party and Jennifer is there with the papers to the bar.
The next scene shows Liotta, Sigourney and Jennifer driving home from the bar. Sigourney tells Liotta that the IRS agent conned her and actually took all her money. They have to get her back.
Next we see Liotta talking to the IRS agent at dinner, having a romantic evening. Waiting outside is Sigourney....