After greeting her friends and love interest Prince Daring, Apple White meets her new roommate, Raven Queen, hoping the latter will follow her destiny to be the Evil Queen so that Apple can have her happily ever after. During rehearsal for Legacy Day, Raven Queen has questions about taking the pledge, and leaves. Headmaster Grimm tells Apple to watch over her roommate.
The students are looking forward to the Spring Fairest and meet two new students from Wonderland. Alistair Wonderland, son of Alice and Bunny Blanc, daughter of the White Rabbit. However, Kitty Cheshire's mother, the Cheshire Cat, swaps the Storybook of Legends for the Riddle Book which causes Apple to be mean to her friends. Now it's up to Raven and everyone else to undo what she did wrong.
When Raven is tricked to sign the Storybook of Legends, the girls find out that the Storybook of Legends is a fake, thanks to Cedar. The girls must find the real book through Headmaster Milton Grimm's forgotten brother, Giles, but instead seek out the spell to break the Riddlish curse placed on him. On the other hand, Briar learns that her destiny might not be as perfect as she thinks, and finds the Storybook of Legends under her room floor. Frightened and confused, she dumps it down the Well of Wonder, where it ends up in Wonderland. Things are about to get topsy-turvy now...
Brooke Page takes over as narrator because her parents have to run some errands. As requested by Apple White, Bunny is tasked to ask Alistair regarding the details of the chess club for the yearbook. Brooke spoils it and claims that Bunny will kiss Alistair, but Kitty objects her statement. At first, Bunny and Alistair start off awkwardly and get interrupted by Kitty, who's watching from afar. Brooke decides on rewinding the scene and this time, making it rain so that Bunny would have no choice but to get closer to Alistair. Instead, Bunny runs off so that she wouldn't embarrass herself any further. For a final attempt, Brooke rewinds and lets the scene play out naturally without any interruptions between the two, and things turn out just as planned.