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.

Oliver tells his parents that he's so embarrassed by their modest house that he'd rather not have a birthday party at all. Katie decides to teach him a lesson by ambushing him with a surprise party at home with all his wealthy friends.

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.