Mr. Dressup, Casey and Finnegan explore and reassure some of the fears that young children have, such as going to school and meeting new people. Then, Mr. Dressup plays a joke on Casey which results in a spat between Casey and Finnegan. Once Mr. Dressup rescues Casey from a locked bathroom, everyone is back to high spirits. At the end of the video, we find Mr. Dressup and Casey out in the backyard putting on one of their famous puppet shows!