Katie tries to help Anna-Kat fit in at school. Taylor and Oliver like the luxe Westport lifestyle.

Greg comes down with the flu and Katie battles exhaustion trying to take care of him and the kids. Her exhaustion leads to a confrontation with the school's overbearing school crossing guard.

Katie tries to fit in with the other Westport moms in order to get Anna-Kat invited to a popular girl's birthday party. When Anna-Kat still isn't invited, Katie vents to Angela and Doris, and realizes her daughter doesn't need a bunch of friends, just a couple of close ones. Elsewhere, Greg tries to convince Taylor that she can't get by on her athletic ability alone, while Oliver complains about a flawed polo shirt that his mom bought at an outlet store.

Doris insists that Katie attend the charity polo match she's organizing.

Katie has been avoiding the mandatory volunteer hours at her kids’ schools all year. But when the other moms pressure her, she hits on a genius excuse after wearing a fake pregnancy “empathy” bump leads everyone to think she is pregnant. But things soon get out of hand after her former frenemies plan a baby shower for her.

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. Taylor and Greg disagree over whether or not she needs to go to college while he teaches her how to drive.

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.

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.

While Greg enlists Oliver and Anna-Kat’s help to drum up new recruits for the Westport Historical Guild, Katie does her best to support Taylor’s dreams of becoming the next American Idol.

Greg hosts a meeting for the Westport Historical Guild to welcome back Stan, and Katie’s homemade lasagna is a huge hit with the guys. After Stan makes several trips back for seconds and begins spending an inordinate amount of time at the Otto house, Chloe Brown Mueller becomes convinced that Katie and Stan must be having an extra-marital affair. Meanwhile, Angela and Doris step in to help Oliver with his Teen Help Line.