Plot
John Plummer is engaged to Elaine Warner and intends to use their life savings of $30,000 to put a down payment on a house. He works for Elaine's father, Mr. Warner, who dislikes John.
Simultaneously, John's niece Noreen, daughter of sister Patty, is accepted to Harvard University, but needs an additional $30,000 on top of her grants and scholarships. Noreen shows John an old videotape where he promised to pay for Noreen's college. He now has a moral and financial dilemma – disappoint his fiancée or disappoint his niece and ruin her chance at escaping poverty.
John confides in his friend Walter "Duff" Duffy, a landscaper. He convinces John to steal from one of his rich clients, who keeps large amounts of cash in an unlocked safe. The pair set off to steal the cash, but Duff runs away when lights come on in the home, leaving John to get caught by Emmett Cook.
At gunpoint, Cook forces John to cross-dress and role-play the part of Cook's late wife as the two men lie in bed and "spoon". Eventually, after taking an incriminating photograph of John, Cook releases him. As he is leaving, Mr. Warner rides by and takes note of John's panicked behavior, believing that he has caught John in an affair.
Further capers ensue as John and Duff try to rob a liquor store and later attempt to con a drug lord out of $30,000 by concocting a phony story about running an ecstasy ring. A police detective is on to John and Duff, but never has enough evidence to actually pin any of the crimes on them.
Meanwhile, Mr. Warner breaks into Cook's residence in order to get evidence against John, and when Cook catches him, he is forced to "spoon" as well. Despite this, Warner finds a common ground with him as he is also widower though he doesn’t agree with Cook’s method of coping. Before leaving, Warner finds the photo of John from the album, which he then gives to Elaine.
John is forced to confess everything to Elaine, who is not upset but admires the lengths he was willing to go to in order to please her and send his niece to Harvard. She then confides in him that her father keeps a great deal of money at his business, and that it would be easy for them to steal it.
John, Elaine, and Duff set out to rob the business in the night. Unfortunately, Mr. Warner had hid his dog Rex inside the vault. Rex latches on to Duff’s crotch, and oddly, enjoys it so much that he doesn’t let go. Just as John and Elaine find the money, Mr. Warner tries to attack them but he is caught by the detective who mistakes him for a burglar.
While Duff is relentlessly pursued by Rex, John and Elaine escape to Duff's van. The police arrive and the gang unsuccessfully tries to get away. They are all taken into custody by the detective and face a series of charges. John feels doomed, until the judge in charge of his arraignment turns out to be the gun-toting Emmett Cook.
Upon their mutual recognition, John flashes a written message to Cook, threatening to expose the judge's fetish; upon reading the note, he quickly dismisses all charges against John. Finally, Duff comes through as best he can and gives John his life savings of $1,000. John uses it to bet on a long-shot horse, which wins and pays out 30 to 1.
John and Elaine are married, Noreen goes off to college, and, in the final scene, John is left to ponder how Duff could possibly accumulate $1,000. The last scene shows Duff offering to "spoon" with Cook for $1,000.
