After learning his girlfriend, Kim (Taylor), is cheating on him, an under-grad college student, Trips (Rudd), sends a breakup letter to her with a fake "used" condom and a topless picture of him and his stripper friend, Ivy (Witherspoon). After learning he was wrong, he tries to stop the letter. He has to face a hostage situation, a psychotic delivery man, and many miles to drive to his girlfriend with Ivy. But, will he fall for Ivy instead of Kim???