Shaun Brumder, an exemplary student and class president at Vista Del Mar High School in Orange County, California, has always dreamed of attending Stanford University. He shares a home with his mom, Cindy, who has remarried, living alongside Bob, her wealthy but wheelchair-bound husband who relies heavily on medication to function. Their household also includes Shaun's aimless brother, Lance.
Shaun begins narrating his story as he writes a heartfelt letter to Stanford professor Marcus Skinner, the author of "Straight Jacket," a book that profoundly impacted his life after he discovered it on the beach. This significant moment is punctuated with flashbacks that highlight Shaun's journey. Despite his academic prowess, Shaun struggles with one major setback: his affinity for surfing with his friends Lonny, Arlo, and Chad. Their allure is irresistible, especially when a perfect wave beckons, even at the cost of more pressing responsibilities.
As they mark the anniversary of Lonny's passing, Shaun's life takes unexpected turns, involving a series of mishaps that threaten his aspirations. One morning, Shaun's maid, Lupe, fed up with Cindy's constant nagging and heavy drinking, contemplates quitting, but Shaun convinces her to stay, needing her help to care for Bob.
After Shaun sends his life-changing letter, complications arise involving Lance, who desperately asks Shaun for urine to pass a test for his parole officer. This culminates in a tense confrontation with the school guidance counselor, Ms. Cobb, who mistakenly sends Shaun's application with another student's poor transcript. This mix-up fuels Shaun's determination to uncover how Tanya, a self-absorbed cheerleader, managed to secure a place at Stanford, ultimately leading him to a critical home visit with Mr. and Mrs. Gantner, Tanya's wealthy grandparents.
The Gantners' visit spirals out of control due to a series of comedic yet disastrous events, including Cindy's drunken antics, Lance appearing inappropriately dressed, and a rescue dog wreaking havoc on the scene. This chaotic encounter ends with the Gantners rejecting Shaun’s application, stating he will never be admitted to Stanford.
Feeling defeated but not willing to give up, Lance concocts a daring plan for Shaun to pose as a Stanford student, taking them on a reckless drive towards the prestigious university. In the meantime, Shaun's confrontation with his affluent father, Bud, reveals personal conflict, as Bud refuses to use his wealth to assist Shaun’s dreams, insisting that Shaun must carve his own path.
Upon reaching Stanford in the dead of night, Shaun and Ashley, his girlfriend, meet Mona, the admissions receptionist, but are faced with another setback when hanging out results in a series of unfortunate yet humorous events that involve engaging with Dean Durkett and his chaotic family.
As the night unfolds with unexpected turns, including Lance getting involved with Mona and setting a blaze in the admissions office, a sense of camaraderie and adventure weeks forward the group into a mixture of chaos and excitement. During this series of escapades, Shaun has a chance encounter with Professor Skinner, who recognizes and praises Shaun's writing talent.
Ultimately, Shaun's journey leads him to realize that he doesn’t need to attend Stanford to pursue his passion for writing. In a heartfelt resolution, Bud decides to donate significantly to the university, but Shaun chooses to stay true to himself, opting to fulfill his aspiration as a writer in Orange County. The film concludes with Shaun burying his copy of Skinner's book on the beach, symbolizing hope for the next dreamer to find it.
