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.

Allen Gregory decides to find his biological mother Lisa Kudrow,until he realizes its a terrible mistake.

Allen Gregory's teacher Gina seeks to teach him a lesson on racism after he mistakes his Hispanic schoolmate Guillermo 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.

When popular student, Joel Zadak, stays home sick, Allen steps in to keep tabs on his clique; Richard visits the boardroom at his father's company.

Tension occurs when Joel Zadak invites Allen Gregory's best friend Patrick and not himself to the school dance.

Allen Gregory attempts to make a sex tape with Principal Gottlieb. Meanwhile, Richard and Jeremy recruit some cool kids to hang out with Julie to make her seem cool.

Because of recession, successful seven-year-old Allen Gregory DeLongpre has been forced to attend elementary school. But because of his maturity, he has difficulty fitting in.