College student Wyatt (Paul Rudd) is convinced that his hometown girlfriend, Kimberly (Christine Taylor), is cheating on him. Disconsolate at a strip club, he nonetheless tries to defend the honor of Ivy (Reese Witherspoon), one of the dancers, who befriends him for his gesture. Ivy convinces Wyatt that he should send Kimberly a vicious breakup letter, which he does, by express mail. When he has second thoughts, he and Ivy hit the road to retrieve the note before it reaches its destination.