Katie and Greg dislike Taylor's new boyfriend, so they attempt to use reverse psychology to drive a wedge between them. After Spencer's over-the-top vision for Oliver's first date with a girl from his ballet class bombs...
Katie's efforts to get more time for herself backfire when she is forced to mend fences with the Westport moms by volunteering to run the school's spring gala. Meanwhile, Oliver proves to Katie that his passion for ballet is genuine, inspiring her to confront his belittling teacher and stick up for him.
Katie knows terrible ideas when she hears them, and she knows how to shut things down. When Anna-Kat gives feedback to a little boy, Katie and Greg recognize the harsh negativity as a mirror of Katie. The Ottos work on supporting loved ones' ideas. Greg wants to roast a pig while wearing a tank top, as he saw Anthony Bourdain do on TV. Katie wants to pitch "Beach Blanket Bingo" as the gala's theme. The kids pay attention and apply the concept of supporting loved ones' ideas, but Tara amps up the animosity towards Katie.
When Anna-Kate brings home a lice infestation, Katie uses it to force bonding time with Taylor. Greg attempts to bond with Oliver by camping in the backyard, but Greg becomes concerned when Oliver keeps ditching their campout to be with their new sleazy neighbor, Spencer.
Westport is known for its Halloween tradition of leaving an anonymous note and goodies on a neighbor's doorstep - called a "boo." Katie is absolutely giddy when the Ottos receive their first "boo," only to find out it was put there by accident.
Katie supported Greg to model better behavior for Anna-Kat, and now she must face the consequences of this support. Hans Gruber is still with the Ottos; Anna-Kat is happy but Katie isn't, and Greg hatches a plan to manage him too. Oliver works to ingratiate himself to Spencer enough to become his sole heir, and Katie tries to use another to create distance in their relationship.
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.
Katie fails to get donations on her terms and enlists Oliver's help to bribe the families in Westport to donate great items for the spring gala. Greg takes his daughters to a Revolutionary War reenactment.
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. Meanwhile, Taylor coaches Oliver on the best way to ask out a crush.
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 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. 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.