Van Wilder starts his freshman year at Coolidge College and embarks on an adventure to land the campus hottie and liberate his school from sexual oppression and party dysfunction.
Just like all the men in his family, high-school student Van Wilder, even before becoming the popular party animal of Coolidge College in National Lampoon's Van Wilder (2002), was already a sexual champion. As he sets foot in the campus as a cocky freshman, Van is shocked to discover that strict Dean Reardon rules the place with an iron fist, restricting alcohol, drugs, and all things sexy. Now, Van must put his charm and wits to good use and do everything in his power to escape from the dean's ROTC program, and get Kaitlin, the hottest girl in school. Has Van what it takes to become a hero?—Nick Riganas
Van Wilder (Jonathan Bennett) has graduated from high school. He is supposed to go on a trip to Amsterdam with his dad (Linden Ashby), but his dad is busy with work, so Van ends up going alone. Van ends up going to Coolidge, following family tradition. His family has their name on a building there, Wilder Hall. However, when he gets there, Coolidge is no longer the fun loving school of his dad's time, but a military-based institution run by Dean Reardon (Kurt Fuller). Reardon, a military man who hates the senior Wilder, wants to make the younger Wilder's life miserable. He can't force him out because his dad is rich and has ties to the school, so he tries to make Van's life a living hell.
Van turns a one bedroom dorm into a two bedroom (by breaking down a wall). His roommate is Farley (Nestor Aaron Absera), a pothead from Jamaica. The boys decide to throw a party on campus, which isn't allowed, along with kissing, drugs, booze, sex, or anything else that's 'fun'. The only person to show up to the party is Yu Dum Fok (Jerry Shea).
The boys try to find the girls, but they just find some religious, prudish girls led by Eve (Meredith Giangrande). After she throws blood on them, Van pulls a prank on them during church. Reardon knows Van is behind the prank, so he commands his ROTC students, Dirk (Steve Talley) and his closeted sidekick Corporal Benedict (Nic Nac), on Van, trying to make him crack.
Van falls for Dirk's girlfriend, Kaitlin (Kristin Cavallari), causing Dirk to get even more upset. Kaitlin thinks, lives, and breathes the military, and believes in chastity before marriage. Of course, Van has to shake things up. After playing a military game with Reardon, which results with Reardon stepping down as dean and tasered, Van and Kaitlin are together, and Van decides to finish up at college, while leaving Dirk and Benedict tied to each other in their underwear.
