John Plummer (Jason Lee (actor)) is engaged to Elaine Warner (Leslie Mann), and intends to use his life savings of $30,000 to put a down payment on a house. He works for Elaine's father, Mr. Warner (Dennis Farina), who dislikes John. Simultaneously, John's niece Noreen (Tammy Blanchard), daughter of sister Patty (Megan Mullally), 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. John now has a moral and financial dilemma – disappoint his fiancée or disappoint his niece and ruin her chance at escaping poverty.