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.

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.