Duff (Green) and John (Lee) are best friends, but couldn't be more different. Duff is a confirmed under-achiever and a lifelong bad influence on John. John is a practical, hard working guy who only wants to marry his longtime girlfriend Elaine (Mann).
Elaine and John have vowed to marry once they save $30,000 for their dream house. After years of struggle, John and Elaine can finally afford to walk down the aisle and into their dream house until John's sister Patty (Mullally) calls with the unbelievable news that his niece Noreen has been accepted at Harvard University. Wedding bells are silenced as Patty reminds John of his promise to pay for his niece's college tuition, which costs $29,829 and is due in two weeks!
Unable to tell his girlfriend, John turns to his friend Duff to help him make an additional $30,000 in two weeks. Duff, who is no fan of Elaine's, convinces John to make a short-term commitment to petty crime. John's life quickly unravels as each of Duff's hare-brained schemes spin out of control.