Katie Otto, a confident, unapologetic wife and mother of three, raises her flawed family in the wealthy town of Westport, Connecticut, filled with "perfect" mommies and their "perfect" offspring. Katie's perfectly imperfect world is upended when her neighbor's decision to move notches her up from her ideal social standing and sets her on a path to ensure that doesn't happen, regardless of the consequences.
Katie gives in to the dark side and teams up with Oliver to bribe rich Westport families to donate big-ticket items for the spring gala.
Greg employs an uncharacteristically dishonest tactic to convince Katie to keep Anna-Kat's beloved pet pig.
Westport is known for its Halloween tradition of leaving an anonymous note and goodies on a neighbor's doorstep (called a "Boo").
When Anna-Kat brings home a lice infestation, Katie uses it to force bonding time with Taylor.
Katie struggles with Taylor and Anna-Kat's defiance, as Anna-Kat decides she's now a vegetarian (under the influence of Tara Summers) and Taylor dies her hair blonde without Katie's permission. Greg and Katie help Oliver come to terms with embarrassment after Oliver has a humiliating moment in ballet class.
Despite pressure from Oliver, Greg and her rival, Tara, Katie insists she's going to plan the Spring Gala her way. After Oliver is emasculated by his ex-girlfriend, Greg attempts to teach Oliver how to "man up" by throwing a successful barbeque.
Katie's efforts to get more time for herself backfire when she is forced to mend fences with the Westport moms.