Vance "Van" Wilder, portrayed by Ryan Reynolds, is a self-assured and witty seventh-year senior at Coolidge College, who enjoys a good reputation among his peers. With no intention to graduate anytime soon, Van spends his days zipping around campus in his personalized golf cart, posing nude for art students, and hosting various parties and fundraisers for his classmates. His close-knit circle includes his roommate and confidant, Hutch (Teck Holmes), along with his newly hired assistant, Taj Mahal Badalandabad (Kal Penn), a bashful foreign exchange student from India.
When Van's father, played by Tim Matheson, learns that his son remains enrolled at college for an astonishing seventh year, he pays a visit with the aim of bringing Van home. Upon Van's refusal, his father decides to cut off his financial support, prompting Van to face the harsh reality of potential expulsion due to outstanding tuition fees. To stall for time, he seeks an extension from the registrar, Deloris Haver (Cynthia Fancher). After a night of passion, Deloris hands over the extension paperwork, revealing that a simple request would have sufficed. Van quickly determines he needs to arrange four payments of $5,000 each to avoid leaving school.
Enter Gwen Pearson, played by Tara Reid, who works for the student newspaper. Although she possesses a talent for journalism, her work fails to capture the interest of her fellow students. Given the task of securing an elusive human interest piece on Van, who typically dodges the media, Gwen finds herself in a challenging position. To fund his tuition, Van embarks on a series of amusing ventures—ranging from sexy tutoring sessions to helping students with intimate issues for a fee, and even organizing a naked mile run.
The story takes a turn when the Lambda Omega Omega fraternity, known for their lackluster reputation on campus, approaches Van with a tempting offer of $1,000 to throw an unforgettable party and help elevate their standing. As the party unfolds and Van's influence grows, Gwen, witnessing the success first-hand, writes an article crediting him as the party's mastermind. Initially displeased, Van later realizes that publicizing this could provide the financial lifeline he desperately needs to stay in school. Following a hockey bet lost to Gwen (whose brothers are professional players), he reluctantly agrees to an interview with her, knowing it could mean front-page exposure in the graduation edition of their paper.
Tension escalates as Gwen's boyfriend, Richard "Dick" Bagg (Daniel Cosgrove), learns of her efforts to cover Van and becomes increasingly jealous, scheming to derail their budding relationship. The two men engage in a series of increasingly outrageous pranks against each other, culminating in one particularly notorious incident where they fill pastries with dog semen, igniting chaos on campus.
Despite their growing closeness, Gwen seeks out Van’s academic history in a moment of curiosity and discovers he has intentionally avoided graduation for years, trailing 18 credits short of a degree. Feeling betrayed by her invasion of his privacy, Van distances himself from Gwen, prompting him to reflect on his choices. However, he eventually resolves to graduate—not just for himself, but for both of them.
In a twist of fate, Richard proposes to Gwen. When she rejects him, she seeks Van only to find him tangled up with another woman. As their respective lives spiral, Richard attempts one last conniving act—sabotaging Van’s party by sneaking minors inside and getting them intoxicated, then calling the cops. This reckless act leads to Van's arrest, jeopardizing his future at Coolidge.
Devastated, Van considers leaving until Taj brings forth a rally of support from their peers, urging him to confront the charges head-on. During a university panel, which includes his adversary, Professor McDougal (Paul Gleason), and Deloris, Van's crisis becomes a catalyst for change. He unexpectedly admits to his responsibility for the party, arguing for a chance to earn his degree rather than face expulsion.
In a surprising twist, Professor McDougal casts the critical vote in favor of Van, allowing him to complete his courses in a mere six days. Meanwhile, Gwen seeks sweet revenge on Richard by tampering with his protein shake on the day of his medical school entrance exam, leading to a spectacularly humiliating moment for him.
As graduation day arrives, Van triumphantly completes his finals and learns he has passed. Gwen's article showcases his numerous contributions to school life, his determination to earn a degree, and Richard’s underhanded attempts to ruin him, leading to Richard's ultimate downfall.
The university celebrates Van's graduation with a lively party in his honor, where his father, having seen Gwen's feature, acknowledges his son’s achievements with newfound respect. Ultimately, Gwen arrives to reunite with Van, sealing their relationship with heartfelt affection amidst the backdrop of the celebratory chaos they’ve created together.
