Sixteen-year-old Regina is very different from the Regina known by fans of ABC’s Once Upon a Time. She seeks romance, adventure and approval. Of course, getting approval from a mother like Cora is next to impossible. For Regina, friendships have always been a rare commodity. Could it be that Regina has finally found a true friend? Or is it too good to be true? As Regina struggles to find her own identity and create her own destiny, she discovers that her fate might just be to become everything she despises.
Chapters 1 to 5
It is Friday, May 5th. Regina is trapped in her room after her mother Cora locked her in. From outside the door, Cora warns her to stay in until she gives her permission to come out. Regina grudgingly agrees, and after hearing her mother’s retreating footsteps, she takes off her riding jacket and boots as she tries to make herself comfortable during her indefinite imprisonment. She sits down on a rug that her father Henry gifted her, which has a scenic design on it of a pond with various animals. Regina then recalls a memory from ten years earlier in September when she was crying over Cora’s refusal to allow her to play with a pair of girls in town. Henry comforts his daughter by telling her a story of an old man who often went to a brook to share food and a song with the animals there. In the story, the man encounters a snake, whom he offers a piece of bread, despite the snake cautioning him of its poison. The snake bites him, but the man soaks his wounded hand in the brook’s water, where a fish sucks out the poison, although the man assumes it just the water lapping at him. The man survives and returns the next morning, where the same thing happens to him. On the third morning, the snake informs the man that he will continue to bite him, to which the man replies it’s in his nature to keep offering him food. Regina doesn’t understand the story, but Henry assures her that someday she will. An hour into Regina’s confinement, Henry comes to escort her to tea on Cora’s request. Henry talks about the foxhunt he went on with his friend Giles Spencer, who is also the royal doctor. Regina looks down on Giles for being a drunkard, but Henry reminds her that Giles changed because of losing his wife and baby. After putting on a dress, Regina passes by her parents’ wedding portrait in the hallway. She recalls thinking as a child that true love was reflected in their eyes, but in actuality, there was so much more hidden in their expressions.
Regina arrives to the dining room and Cora introduces her to Claire, Giles’ niece who has come to live with him for the season. Claire tells Regina about how Cora found her in Port Bennett, and upon learning she was a relation of Giles’, Cora encouraged her to leave for better marriage prospects since the port town often draws unsavory men. Regina is fascinated by the idea of meeting bandits and pirates but feigns outward disdain. She notices Claire wears a ring around her neck, one that has a dragon claw curved around a red stone, and reminds herself to ask the girl about it at another time when Cora is not around. Solomon, one of the servants, delivers an invitation from King Leopold and Queen Eva to come to their castle and celebrate the end of the Ogre Wars. Claire is excited over meeting the Queen as she has heard wonderful things about her, however, Cora mentions that, had it not been for Eva, she would have never married Regina’s father. To sate Claire’s curiosity about this happened, Cora recounts being a miller’s daughter and delivering flour to King Xavier’s castle, where the then Princess Eva tripped her and complained about Cora ruining her shoes. Cora admits Eva hated her as she previously stole the heart of Eva’s intended groom, Leopold, but after things did not work out between Cora and Leopold, Eva and Leopold ended up together. To finish the tale, Cora explains showing up at King Xavier’s ball and proving her ability to spin straw into gold, which won her a marriage proposal from Xavier’s son Henry. At the dining table, Regina reaches for a biscuit, but Cora slaps her hand away, telling her to abstain from baked goods if she means to become Queen one day. As Regina silently rages over her mother’s words, Claire bravely speaks up in Regina’s favor. Regina is shocked by the girl's audacity as no one has ever stuck up for her before, and she becomes fearful of what Cora's reaction will be. Cora, much to Regina’s relief, calmly agrees with Claire. Regina then thinks to herself about how fortunate she is to have Claire as her friend. 
The next day, while Regina is in the stables grooming her horse Rocinante, Claire drops by to join her for a ride. Another horse, Opal, is prepared for Claire. Regina asks for her help to pick a red apple that blossomed early in the orchard. Claire provides a boost to get Regina higher up into the tree. Regina tosses the apple to Claire and then has trouble getting down. Claire offers to catch her but Regina jumps down instead. Using her sleeve to polish the apple, Claire then gives it to Regina, who admires the fruit’s perfect shape and color. The girls return to Regina’s house, where Claire sees a family portrait with the artist’s name on it: Jasper B. Holding. Regina gushes about Jasper’s talent despite only being eighteen and that he is her art teacher. Claire notices Regina is blushing and wonders if she has a crush on him. Regina denies it.
In February three months earlier, Regina, her parents, and the family dog Thaddeus pose for Jasper, who is painting a portrait of them. Regina thinks of how she feels under the scrutiny of Jasper’s gaze when he is painting her and how drawn she is to his eyes. Weeks later when Jasper delivers the finished portrait, Regina asks if he can teach her to paint. Cora agrees to the arrangement. During the first art lesson, Regina paints a picture of Rocinante. Jasper is impressed by her ability to paint a horse, but helps her improve her drawn trees by adding texture and bumps to look more realistic. He advises her that nothing found in nature is truly perfect. In present day, Claire has her first glimpse of Regina’s room. Regina learns about Claire’s family and how her uncle Giles became the royal doctor. The girls end up having a pillow fight and making a mess of the room. A servant, Rainy, helps prepare a picnic basket for them, while Claire borrows some of Regina’s riding clothes. Rainy notices the apple, which Regina proclaims she will gift to Jasper.
On the ride through a meadow, Claire has trouble slowing down Opal until Regina aids her. They reach a hill overlooking King Leopold's castle, where Claire asks Regina if she has ever been inside. Regina opens up to her about her fears that Cora will retaliate against the Leopold and Eva for the humiliation she suffered in the past. Following this, Regina leads Claire towards the royal gardens to have their picnic, but on the way there, the two encounter a blind woman on the road. The woman asks for a ride home, and Claire convinces Regina that they should help her. The trio quickly reach the woman's home: a cottage made of confections. Both girls are drawn in by the smell of sweets, but it is Claire who persuades a reluctant Regina to accept the woman’s invitation to stay for tea.
Chapters 6 to 10
Chapters 11 to 15
Chapters 16 to 20
Chapters 21 to 25
- The Enchanted Forest present events takes place several years after "Sisters" and not long before "The Queen Is Dead". The story also takes place seventeen years after Cora and Henry's wedding in "The Miller's Daughter" and sixteen years after Regina was born in "The Miller's Daughter".
- The time span of the novel begins on the morning of Friday, May 5, and concludes on Wednesday, May 24.
- The flashbacks in chapter One and Thirteen take place ten years earlier, six years after Regina was born in "The Miller's Daughter" and a few years before "Sisters".
- The flashback in chapter Seven takes place four years before the frame story and twelve years after Regina was born in "The Miller's Daughter".
- The flashback in chapter Twenty-Four takes place eleven years before the frame story, five years after Regina was born in "The Miller's Daughter" and a few years before "Sisters".