Лето закончилось и Кэти довольна от того, что вскоре сможет «сдать» детей в школу. К тому же Тейлор вскоре может получить права и тогда ей еще и не придется их возить туда. Для полного счастья Кэти нужно, чтобы Анна-Кэт выбрала себе кружок и для этого она даже собирается стать школьным волонтером.

Кэти думает над темой гала-вечера, который она взялась организовывать и Тара не упускает случая напомнить ей, что она вряд ли справится. Тем временем Грег заказал огромный гриль и вынудил жену согласиться устроить барбекю для их друзей. А Оливер опять начал общаться с Элис.

Тара решает отомстить Кэти за то, что та испортила его сына и поэтому она делает из Анны-Кэт вегетарианку. Тем временем с Оливером произошел постыдный инцидент на занятиях балетом. А Тейлор без разрешения перекрасила волосы.

У Анны-Кэт появились вши, и это добавило забот Кэти, которая недавно осознала, что Тейлор уже совсем взрослая и решила сблизиться с ней пока та не получила права и не уехала из дома. Тем временем Грег решил немного пожить в палатке на заднем дворе, чтобы не заразиться от дочери. А Оливер встретил своего кумира – мошенника с Уолл-стрит.

В Вестпорте на Хеллоуин есть традиция вручать самой популярной семье титул называемый «Бу». Отто никогда его не получали, но в этом году он им все-таки достался. Однако как оказалось позже – по ошибке.

Greg plays dirty to convince Katie to let them keep Anna-Kat's beloved pet pig; Oliver and Viv compete for the attention of a new neighbor; Taylor considers leaving her boyfriend.

Greg makes big plans to impress his parents when they visit for Thanksgiving; but his vision is shattered when his neighbor Spencer and Katie’s mom, Kathryn, arrive unannounced and nothing goes as intended.

After failing to get donations on her own terms, 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 decides to take Taylor and Anna-Kat to a Revolutionary War reenactment which Taylor finds lame until she starts a revolution of her own.

When Doris goes into labor and Katie heads to the hospital to be with her, the Ottos struggle to be in the same place at the same time in order to open their Christmas presents together, as is the Otto family tradition. Meanwhile, Taylor coaches Oliver on the best way to ask out a crush, starting with the gift shop clerk.

Taylor enlists Oliver to help her carry out a scheme so she can ditch her less cool friend Ellen and go to a concert with her "blondetourage." Meanwhile, Katie is devastated when Anna-Kat doesn't need her as much anymore, which causes Katie to make some poor and desperate parenting decisions.

Katie is worried that the launch of Greg's new book might go poorly, so she enlists Angela and Doris to write positive reviews; when the book unexpectedly does exceedingly well, Greg buys a new car without consulting Katie.

Katie and Greg dislike Taylor's new boyfriend, so they attempt to use reverse psychology to drive a wedge between them, which later backfires. After Spencer's over-the-top vision for Oliver's first date with a girl from his ballet class bombs, Greg helps Oliver make up for it with a romantic gesture.

Katie takes Oliver out of school for a day to help loosen him up after Oliver suffers from a meltdown about something minor. Meanwhile, Anna-Kat takes Greg to the park to help him make new friends.

After feeling unappreciated by Greg and the kids, Katie ditches her family for a day at her favorite hideaway spot and leaves Viv in charge of the household. Viv takes this as an opportunity to see if she really is mom material.

Katie wants to prove to the Westport moms that she is fully capable of competing at Field Day at Anna-Kat’s school, but she ends up taking the competition a little too seriously. Greg enlists Taylor’s boyfriend, Trip, to help him make the family recipe for chili in a local competition, which makes Taylor and Oliver jealous.

The Otto children are beginning to experience struggles in their love lives after jumping into the dating world: Oliver is forced to choose between his girlfriend and his friend Cooper who come from two different worlds; Greg must play the “bad cop parent” to halt the PDA between Taylor and Trip; and Anna-Kat tries to make her relationship with Franklin official, without his consent.

Katie enlists Angela's legal help to convince Chloe Brown Mueller to sign off on the venue for the Spring Gala, but Angela ends up cozying up to Chloe instead.

Katie and Greg struggle to help the kids accept loss as a family friend suddenly passes away and as their pet pig, Hans Gruber, must be returned to his natural habitat.

After the passing of a family friend, the Ottos all react differently to the allotment of the deceased's inheritance.

Katie and Greg struggle to resist the urge to micromanage as their children navigate life choices, such as landing your first job, picking out friends and managing homework.

When Katie starts her day in a bad mood, the Ottos come together to cheer her up; but in an alternate reality and in a different sweater, Katie starts her day in a good mood and the family comes together to cheer up Greg.

In order to impress the other moms at school, Katie, Taylor and Oliver travel to New York to track down Nathan Fillion at a "Firefly" convention, so Katie can convince him to attend the school's spring gala.

When things start to fall apart at the last minute, Katie figures out a new way to make the spring gala a success. Meanwhile, Greg attempts to be a "fun dad" and winds up adopting a dog while Katie is occupied with the gala.