Oliver is secretly taking dancing and manners classes in hopes of getting the girl he likes to go to the Westport Cotillion with him. He asks for his dad's help in keeping this all secret from Katie, afraid that she'll interfere, but that's easier said than done.

Katie and Greg are thrilled when Anna-Kat finally has a playdate with a "normal" girl. But Anna-Kat has a little secret: She's a budding kleptomaniac and has taken something from her new friend Penny's home. Greg wants her to return the item and fess up, but Katie disagrees, especially since Penny's mom, Chloe Brown Mueller, is one of Westport's most infamous gossips.