Romeo and Juliet Pepper Ann tries out for a play because Craig has the lead role of Romeo. When the time comes around for the results, she's a runner-up to Cissy who's gotten the lead role of Juliet. Pepper Ann got the role of "Nurse." Meanwhile, Milo is O.D.ing on juice boxes. Finally when it's time for the play, Cissy loses her contact lense, and Pepper Ann gets the lead role, but an accident causes Craig to be replaced by a chubby Milo.

Theater ist nicht gerade Pepper Ann?s Leidenschaft. Doch als sie hört, das ihr heimlicher Schwarm Craig Bean aus der achten Klasse in der Schulaufführung den Romeo spielt, will Pepper Ann unbedingt die Rolle der Julia haben. (Text: SuperRTL)

Após saber que Craig foi escalado para o papel de Romeu na produção do Clube de Teatro de "Romeu e Julieta", de Shakespeare, Pepper Ann faz o teste para o papel de Julieta. Pepper Ann arranja um emprego após a escola para aprofundar seus conhecimentos e sua compreensão sobre economia.