Maggie Pearl with her best friend Ginnie-Ree along with Maggie's Grandmother Nanny navigate their way towards the first day of school. Maggie Pearl and Ginnie-Ree have mixed feelings and much anticipation of not knowing what will happen on starting the new adventure of school. At the end with much encouragement and help from Nanny they are successful on their first day of school and excited about the new school year and have solved the question "Wonder if they will let me Play?"