Tim Lippe, an earnest and naive insurance salesperson from small-town Wisconsin, is tasked with representing his company at a regional insurance convention in Cedar Rapids, Iowa, after a tragic event involving a colleague. Having never left his hometown, Tim is overwhelmed by the vibrant, unpredictable environment of the gathering. He quickly befriends three convention veterans: brash and hard-partying Dean, seductive Joan, and straight-laced Ronald. As Tim navigates this unfamiliar terrain, he becomes aware of the professional and personal challenges that lie ahead, while grappling with his own naivety and moral compass. Through these relationships, Tim starts to see the cracks in the façade of not just the convention, but his own preconceptions about life and his job.

Faced with ethical dilemmas and personal temptations, Tim must decide what kind of man he wants to be, even as he is drawn deeper into the whirlwind of the convention's antics. The humor evolves from his fish-out-of-water experiences and the eccentricities of his new friends. As he wrestles with newfound knowledge and perspectives, he learns to balance idealism with pragmatism. What began as a simple business trip turns into a journey of self-discovery, pushing Tim to confront his values, his courage, and ultimately redefine his path forward.