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.

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.