Joel Goodson, a high-achieving high school student from the affluent Chicago North Shore town of Glencoe, is driven by his parents' expectations and his desire to attend Princeton University, his alma mater. His father specifically hopes he will follow in his footsteps, and as part of his extracurricular activities, Joel participates in Future Enterprisers, where students collaborate to create small businesses. With his parents away on a trip, Joel's friend Miles convinces him to indulge in some fun and chaos, leading Joel to explore his newfound freedom in a way he never has before.
On his first night of independence, Joel throws caution to the wind — he raids his liquor cabinet, cranks up the stereo to full volume, and dances exuberantly around his living room in just his briefs and a button-down shirt to the tune of "Old Time Rock and Roll". This carefree moment marks the beginning of a series of increasingly rebellious experiences.
The next day, Miles makes a call on Joel's behalf to a prostitute named Jackie, which initially results in a humorous misunderstanding when she turns out to be a male cross-dresser. Joel quickly pays him to leave but is then given a number for another prostitute, Lana, a striking blonde woman. That night, feeling restless and curious, Joel hesitantly dials Lana, and this decision leads to an intense, all-night encounter that fundamentally changes his perspective on his own innocence and sexuality.
The following morning, Lana requests $300 for her services. Joel heads to the bank, but when he returns, she has already left, taking with her his mother's valuable Steuben glass egg. Driven to retrieve his belongings, Joel finds Lana and demands the egg back, only to be confronted by her pimp, Guido, who pulls a gun amidst the tension. Joel then finds himself chased through Chicago in his father's Porsche 928 by Guido, eventually managing to escape. Lana admits that the egg is with Guido and her belongings, and in the meantime, she stays at Joel’s house while he balances school responsibilities and personal chaos.
In the midst of these upheavals, Lana invites another prostitute, Vicki, to stay over, but Joel, feeling overwhelmed, declines. That decision leads to a confrontation on his front lawn with Guido, who shows up with the other women, resulting in a high-stakes verbal altercation. Despite this turmoil, Joel allows Lana and Vicki to stay for one more night.
One night, Joel, Lana, Vicki, and his friend Barry experiment with marijuana, which intensifies their eve. During this escapade, Lana accidentally bumps Joel’s prized Porsche out of gear, causing it to roll down a hill and plunge into Lake Michigan after crashing through a pier. The costly damage leaves Joel distressed and worried about how to afford repairs. Later, in an ingenious but rebellious plan, Joel and Lana decide to transform his parents' house into a makeshift brothel for a night to make some quick money and fund the car repair. The event turns into a huge party, with many friends and Lana’s co-workers filling the house, showcasing Joel's unexpected ability to throw a successful, chaotic gathering.
This night coincides with an important moment—the Princeton recruiter Rutherford arrives to interview Joel. The interview is disrupted repeatedly, and Rutherford’s impression of Joel takes a hit, but he remains at the party to mingle with Lana's friends. Afterward, Joel and Lana share an intimate moment on a Chicago "L" train, highlighting the depth of their connection amidst the madness.
The next morning, chaos ensues as Joel finds his house burglarized when returning from getting his father's car repaired. His efforts to call Lana are thwarted when Guido answers and demands his furniture back. Despite these setbacks, Joel’s resourcefulness allows him to get everything restored just in time for his parents' return. His mother notices a crack in the prized egg, but his father, pleased with the outcome, informs him that his Princeton acceptance is secured, thanks to Rutherford being impressed by his resilience and experiences.
In the closing scenes, Joel and Lana meet at a restaurant, contemplating their future together. Lana expresses her desire to continue seeing him, hinting at a complicated yet genuine attachment. Joel, with a hint of humor and affection, teases her about the costs involved, suggesting that their unconventional relationship may have only just begun.
Throughout this story, Joel's journey is one of youthful rebellion, self-discovery, and navigating the push-and-pull of expectations versus personal desires, all set against the backdrop of suburban affluence and urban adventure.
