It is 1990 and, while the country stands on the brink of war with Iraq, Kirby Russo is finally at peace with the world. At seventeen years old, he's figured out some important lessons: how to stay out of trouble with the authorities; how to write muck-raking articles that expose the hypocrisy of said authorities; and, most importantly, how to avoid obsessing about his long lost girlfriend Izzy (who has run away and may be in trouble in Chicago). But when a rich classmate snags the editorship of the school newspaper out from under him, Kirby knows his brief career as a conformist is over. An opportunity to reestablish his hell-raising bona fides arises when his long-lost father shows up with a shady past and a half-baked scheme. Together, they embark on a cross-country road trip to connect with a family he never knew, and maybe even track down Izzy. Kirby soon realizes, however, that life's biggest lessons – the ones that really matter – never happen according to plan.