Since his family has fallen on hard times, Allen Gregory De Longpre, one of the most pretentious 7-year olds of our time, is forced to face his greatest challenge - attending public school to enter the first grade.

After discovering that his rival classmate Joel Zadak has a girlfriend, Allen Gregory sparks a sex tape scandal with Principal Gottlieb.

When Allen Gregory's doting - and comically malevolent - dad, Richard, helps plan Allen Gregory's first school dance, tension occurs after popular stud Joel Zadak invites Allen Gregory's trusty friend, Patrick but not him.

When Joel Zadak stays home from school because he's sick, the always presumptuous Allen Gregory steps in to help his popular “friend” by keeping tabs on the clique.

Allen Gregory's teacher, Gina, seeks to teach him a lesson after he mistakes his schoolmate for a janitor. Much to Gina's dismay, Allen Gregory produces a play to depict his point of view of the incident. Meanwhile, Richard hires Jeremy as his new maid.

Allen Gregory enlists the help of a friend to find his biological mother. Though Allen Gregory initially dreams of his mother and father falling in love and starting a life together, he soon realizes that this new "family" is not all it's cracked up to be

The persistent and pompous Allen Gregory bribes Principal Gottlieb into a romantic situation that he hopes will bring them closer together. Meanwhile, Richard uses Julie to compete with his frenemy's adopted child.