After Anna-Kat's big win with The Wildflower Girls, the Ottos head to California for an all-expenses paid family vacation. But when her birthday coincides with their trip, Katie is determined to have a relaxing kid-free day, one where she and Greg are free to do whatever they want. Meanwhile, Taylor loses all her money on Hollywood Boulevard and Anna-Kat is forced into busking to get them out of trouble; and after crashing their trip, Cooper surprises Katie by making her birthday wish come true.
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. She lets us in on her deepest, most unfiltered thoughts through voiceover as the she lives her life as the second fattest housewife in Westport.