After the previous "fattest housewife" in Westport gets plastic surgery to lose weight, Chloe Brown Mueller rubs it in Katie's face that Katie has now assumed that title. In order to get revenge on Chloe, Katie goes through great lengths to dig up bad photos of Chloe from high school. In discussing body image with the kids, Katie and her mother, Kathryn, turn out to be bad influences on Anna-Kat and Taylor, unintentionally encouraging them to focus too much on the outward appearance. Over time, Katie realizes how judgmental she has become and that she is part of the problem.

Katie lands the perfect pawn to play on the insecurities of the Westport housewives when she convinces a hot young trophy wife named Harper to volunteer as room mom for Anna-Kat's class, but she quickly shifts gears when Harper rejects Anna-Kat's idea for movie night. Meanwhile, Greg enlists the help of the kids to get Katie's mom, Kathryn, to take an interest in someone other than herself,.