Van Wilder (Jonathan Bennett (actor)) has graduated from high school. He is supposed to go on a road trip to Amsterdam with his dad (Linden Ashby), but his dad is busy with work, so Van goes alone. Van ends up going to Coolidge College, following family tradition. His family has their name on a building there, Wilder Hall. However, when he gets there, Coolidge is no longer the laid-back school of his dad's time, but a military-based institution run by Dean Reardon (Kurt Fuller).