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.
As the Otto family ushers in a new era, Katie and Greg make the emotional decision to sell the family minivan; Daniel suffers a setback that forces him to rethink how to accomplish his goals.
Katie's life is turned upside down when her notoriously elusive boss Whitney pops into town and promotes Katie; a colleague's death pushes Greg toward an existential crisis.
When Anna-Kat's school lunch lady refuses to make simple eco-friendly changes in the school cafeteria, Greg puts on a show highlighting the importance of recycling with his friend and fellow environmentalist Bill Doty.
When Greg hosts a meeting for the Westport Historical Guild to welcome back Stan, Katie's homemade lasagna is a huge hit with the guys; Angela and Doris step in to help Oliver with his Teen Help Line interview.
Katie ignores Greg's warning and takes Anna-Kat through a terrifying zombie-themed maze at the annual Halloween carnival. Once inside, Katie quickly regrets her decision and sends Anna-Kat to find help. Meanwhile, Greg has entered a pumpkin carving contest and is ready to go head-to-head against the previous year's winners.
With Katie's 40th birthday fast approaching, her self-esteem starts to wane. So Greg encourages her to go out and enjoy a night on the town with the girls, even suggesting she leave her wedding ring behind for a night of faux-single, silly fun. Meanwhile, Angela receives devastating news that will turn Doris' life upside down. While Katie is away, Greg enlists the kids' help to create a birthday present that is a heartfelt reminder of how much she is loved.
Katie teams up with Oliver in hopes of growing her lasagna-making endeavor from hobby to serious business venture. Meanwhile, a bout of writer's block forces Greg to look at new career opportunities. When a young YouTube sensation enlists Greg's help to ghostwrite his memoir, Greg is pushed out of his comfort zone
Katie's feud with Chloe Brown Mueller is reignited when Oliver discovers Chloe's attempts to sabotage Katie's lasagna business. Meanwhile, Anna-Kat and Franklin play matchmaker for Principal Amblin in an attempt to secure more privileges.
In an effort to stay connected, Katie and Greg look into activities that they can enjoy as a couple. Meanwhile, Anna-Kat has her own hurdles to overcome when Franklin shines at square dancing and she fails miserably. Plus, Tripp struggles with the idea of Taylor going away to college.
Katie looks forward to sharing her favorite childhood Christmas tradition with Taylor, but a surprise visit from her mom threatens her holiday cheer; Greg is blindsided by Katie's good intentions; Oliver and Anna-Kat break a family heirloom.
When Anna-Kat begins exhibiting past OCD behaviors, Katie and Greg worry their busy schedules are disrupting the family. Meanwhile, Oliver fields a call at the Teen Help Line center that rattles him. And, Taylor and Trip attempt a trial run at being in a long-distance relationship.
Katie grows concerned when Anna-Kat is invited to join Westport's elite scout troop. Taylor learns her Carnegie Mellon interview is scheduled with famous alumnus and Broadway star Brecken Phillips. Oliver befriends the school recluse.
Katie is determined to help Anna-Kat win top prize in cookie sales against her fellow troop members, The Wildflower Girls; Oliver's attempt to help a student he befriends through the Teen Help Line center backfires.
Against her husband's wishes, Katie sets out to play matchmaker for British Greg. Meanwhile, Oliver goes along with a rumor at school about his sexual identity to help a classmate feel accepted.
Katie finds an old piece of furniture in the basement and sets out to recreate her and Greg’s first apartment, reminiscent of a time when life was simpler. Meanwhile, Greg enjoys an unexpected benefit of being the victim of Lonnie’s relentless practical jokes.
Katie begins to feel like the third wheel when the topic at second breakfast starts revolving solely around Angela and Doris’ new relationships. Meanwhile, Greg struggles with Anna-Kat’s newfound independence.
Katie reminds Anna-Kat that she is a strong, independent, young woman and encourages her to start standing up for herself when dealing with Taylor. Meanwhile, Oliver feels left out when Greg invites Lonnie, Trip and Franklin to join him at the Historical Guild’s latest reenactment.