Katie must mend fences with the Westport moms by volunteering to run the school's spring gala. Meanwhile, Katie confronts Oliver's belittling ballet teacher; and Taylor and Greg disagree about the necessity of college.
Katie plans the spring gala her way, despite pressure from Oliver, Greg and Tara. Meanwhile, Oliver is emasculated by his ex-girlfriend, so Greg attempts to teach him how to man up by throwing a successful barbecue.
Taylor dyes her hair blonde without Katie's permission. Meanwhile, Anna-Kat decides she's now a vegetarian; and Greg and Katie help Oliver come to terms with embarrassment after Oliver has a humiliating moment in ballet class.
A lice infestation occurs in the Otto household thanks to Anna-Kate, and Katie uses this as an excuse to bond with Taylor. Meanwhile, Greg and Oliver camp in the backyard, but Oliver keeps ditching their campout to hang with their sleazy new neighbor.
The Ottos receive a "Boo", which is a Westport tradition of an anonymous note and goodies being left on a neighbor's doorstep, and Katie is absolutely giddy about it, but then they find out it was put at their door by accident.
Greg sides with Anna-Kat about keeping her beloved pet pig, despite Katie's objections, and he even plays dirty to win this battle. Meanwhile, Oliver and Viv compete for the attention of a new neighbor; and Taylor considers dating an older guy.
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, arrives 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.
After feeling like their whole world and all of their conversations revolve around kids, Greg and Katie are ecstatic to meet new friends Zach and Courtney, a couple without children. Meanwhile, Anna-Kat coerces Taylor and Oliver into helping her with a storytelling project, which turns out to be a little more grisly than anticipated.
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 of the book online to boost his confidence. 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 takes things too seriously at a field day competition; Greg makes chili for a competition.
The Otto children 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. Nathan Fillion guest stars as himself.