After convincing Zuri to enter a pageant, Jesse runs into her nemesis Nanny Agatha, who has entered her beloved Lindsay in the pageant, as well. Meanwhile, Luke and Ravi play practical jokes on Bertram.

Emma and Zuri plan a romantic mystery-filled fifth first date for Jessie and Tony. Meanwhile, Ravi, Cameron and Bertram get stuck in a giant teacup on a billboard, after their failed attempt to rescue Ravi's toy helicopter.