When her little brother Tyler is nervous about his first day of school, Pinky Dinky Doo tells him a story about the time she and her friends had really bad hair days when school pictures were scheduled.
A child describes all the colorful characters she met on her "very first school day ever," from three-headed dragons to an ape who prefers to stand on five toes.
Charlie, who is nervous about his first day of school, and Dumpy the Dumptruck, who is nervous about his first construction job, gradually adjust to their new settings after making new friends.