- Chapter 1: Beyond Boring
As she takes Damsel-in-Distressing, Darling Charming's homework assignment is to wait and sit perfectly for one hour and she's sick of it. Her roommate Rosabella Beauty assures her that her tedious waiting isn't as bad as the treatment of ogres and beasts. Rosabella is quite glad that she doesn't have to take Damsel-in-Distressing because it's not really of her story, to Darling's slight jealously.
- Chapter 2: Pretty Is as Pretty Does
When she was younger, what bothered Darling was that people of the Charming kingdom never looked beneath her surface as all they did was shower her with compliments. As she was a child with above-intelligence and advanced learning, nobody seemed to care. And "traditionally", as a damsel, she was obligated to do nothing and watch her brothers have all the fun. Each time when Darling did try to be like her brothers, her father would immediately stop her. Her mother gave her a lecture on why she can't be like her brothers and that she has her part to play as a damsel.
- Chapter 3: Strong Is as Strong Does
As soon as Rosabella leaves from the dorm, Darling gives up on the waiting assignment and won't let her remaining minutes go to waste. Instead, she pulls out workout clothes hidden deep in her wardrobe (which would have been forbidden in the Charming household) and starts doing thirty push-ups, and continues to do fifty sit-ups and ten chin-ups. As she starts doing her lunges, a bouquet of flowers land at her feet. Darling gets these at times and waves thanks to the boy who threw them up to her, not wanting to be seen in her current get-up. Although waving is considered polite, Darling was constantly given flowers to the point where the cleaning ladies got angered as soon as they had to clean out the wilted flowers. The boy bravely "confesses" his love to Darling but she turns him down, knowing all too well that he, and several others, do that just to marry their way into the Charming family so that they can get privileges.
As soon as the boy leaves, Darling continues exercising and she's been practicing how to do so in small spaces - using the Grimmnasium would be too risky. Suddenly, Darling hears a disturbing noise. She gets changed and heads down. The noise is coming from Dexter, dressed up in armor and riding on horseback. Dexter is helped back upright and it shows that he's not cut out for the class, to Darling's dismay. There she meets Apple White, who gives her the love letters accidentally sent to her dorm. Apple expresses how much she enjoys answering the love letters. Darling, on the other hand, disagrees and would rather give her destiny to any girl student who'd want it. With Dexter just sitting there and with Seeing that Hero Training has come to an end, she tries to find a way to get to the garden in the nick of time. She uses a large vine to get to class by swinging all the way down, despite getting calluses on her fingers.
- Chapter 4: The Tower Years
The Charming Castle was on top of a craggy, steep peak. Uninvited visitors usually have a hard time reaching it. The castle itself is natural disaster-proof. But a notable thing of this castle is the tower; a tower that's old and dusty and a tower Darling has to spend most of her life in until she is to be rescued. When Darling was younger, a few suitors showed up at the Charming Castle's front doors and King Charming easily dismissed them. Daring and Dexter chased the boys out. This would normally happen if Darling went to another village or ball, and until Darling is to be sent to Ever After High, King Charming has decided that she is to be kept in the Charming Castle until then. As the years passed, Darling realized how the damsels have not really been thinking about how to escape towers.
As such, Darling trains regularly so that she is fit enough to climb out of her tower once she's to be put there so she doesn't need a man to rescue her.
- Chapter 5: Dexter's Dilemma
Back at the school, Darling gracefully makes her way through the premises until she reaches the school gardens, she notices that Ever After High is holding their annual Parents Weekend. Rest assured though, she is aware that her parents won't be attending. Headmaster Grimm strolls on campus and finds Darling. He tells her about how her father called in to check on her, but Darling informs the headmaster that King Charming won't be attending Parents Weekend. Making her way to the fields, she finds an upset Dexter slumped down. He expresses his worry because he's falling behind as the one student who can't joust. Darling reassures him and is sure that he would rather joust than wait and do nothing.
- Chapter 6: Overly Perfect
When Dexter was a boy, he always had trouble traveling around Charming Castle because he kept bumping into walls. The physician insisted that Dexter wear glasses, but not because his eyes are imperfect. Instead, he classed them as "overly perfect" vision. From that day forth, Dexter was the first Charming to ever wear glasses. But at present day, Dexter shows that his glasses are a hindrance when jousting. Darling suggests that the helmet should get modification to fit his glasses in as well. Dexter is just slightly relieved that even if he jousts on Parent's Weekend, his parents are not to see him fail if he does. Darling receives a text from her mother that they have rescheduled their cruise so that they can attend Parents Weekend. Because Dexter is less-than-confident in the jousting fields, Darling offers a switch.
- Chapter 7: The Village Smithy
Dexter and Darling visit the Village of Book End. They find a blacksmith's shop and enter it. There they meet the blacksmith, or "smithy" called Betty Bunyan, daughter of Paul Bunyan. Betty immediately recognizes the Charmings and tells Dexter about how Daring's armor is quite flawless whenever he brings it in. Unbeknownst to Betty, Dexter is quite hurt by the comparison. Daring gives him words of support and explains to Betty about their helmet issue. Betty notes that if Dexter needs it by the weekend she is unable to do it on time, but Darling asks if she would make the helmet if Daring requested it made. Betty takes that fact into consideration and will try her best to make the helmet.
- Chapter 8: The Stress of Being Distressed
Darling walks in the Damsel-in-Distressing room with an accepted love note given by a boy student in hand. Duchess insensitively and sarcastically notes how lucky Darling is to get such love notes. After the headmaster gives a short announcement to the girls of the class, Maid Marian enters with not much welcome from the headmaster. Maid Marian herself isn't too keen on teaching such a class, but she asks the students to turn in their waiting homework as they proceed onto the next syllabus, which is listening to a cassette tape of recognizable sounds.
- Chapter 9: Gallant Sir Gallopad
Equipped with her workout getup, Darling slips out of the dorm room at night when everyone is asleep. She sneaks over to the stables to fetch her pet, Sir Gallopad, as her plans for the night are to escape school campus and return before dawn so that the wall of briars can disappear and scatter. Darling and Sir Gallopad rest in the Enchanted Forest. The next morning, Darling stumbles across a strange arrow left nearby when she wakes up, but she leaves it where it is and leaves. She does as follows and heads back to school. As soon as she returns to her dorm, Darling thinks about the odd arrow that was shot next to her, but it wasn't there when she fell asleep so someone else must also have been past curfew.
- Chapter 10: Bad News Betty
Darling and a few others have a late breakfast in the castleteria. After a short announcement from Headmaster Grimm and a weather announcement broadcast, Dexter calls Darling over and notifies her that he is coming down with illness and makes Darling promise not to tell anyone that he is to visit a doctor soon. Darling is expecting Dexter's jousting armor and helmet to be done, so she calls Betty for a delivery to Dexter's room as a nice surprise. However, Betty does not answer the phone and Darling decides on checking in on her herself in Book End. After causing a few accidents and collisions by her presence in Book End, Darling makes her way to the shop and finds that Betty has left to visit her father who has a bunion removal at the hospital and will be back in a few weeks, and Parents Weekend would be far from over. Considering that the armor would be hard to carry out in the open, Darling fits all the pieces together and steps out with the helmet on.
- Chapter 11: If the Suit Fits
Darling wears Dexter's armor out as it is easier to carry that way prior to leaving Betty a note. Darling enjoys how she isn't getting the unneeded attention disguised in the armor as she walks around in Book End. While wearing Dexter's armor, Darling runs into Daring, Hunter and Professor Knight. They soon make their way back to Ever After High where they do jousting practice, much to Darling's excitement.
- Chapter 12: Princely Pox
After entering Dexter and Hunter's dorm room, Darling discovers that Dexter has caught the princely pox and will recover in a few days, but the situation bears both good and bad news because Dexter didn't care about jousting, but he had to get better. Darling also tells him about his status in class as the most improved because of her help. Because of his current state and now that expectation of Dexter's jousting skill has been raised, Dexter is quite angry and speechless at Darling, who is really sorry. She then reveals that she still continued training in secret after they left the Charming Castle for Ever After High, but that still made Dexter upset because now he's not the second best anymore. But now Darling wishes to make it up to Dexter, somehow.
- Chapter 13: A Cry for Help
At Damsel-in-Distressing class, their next part of the syllabus is calling for help. As everyone eventually gets the hang of it, Darling finds it rather humiliating to take part. Because of all the ruckus, the headmaster even notifies them that they're disrupting other lessons, but because it's part of the curriculum he lets them off. After class, Maid Marian requests to speak with Darling and is aware that she's not the princess everyone thought she was, also acknowledging the fact that she's acting Rebel.
- Chapter 14: Banned Books
When Darling was a younger age, she was able to judge a book by its cover, quite literally. Although Darling liked reading, she also liked going on real adventures like her brothers. Dexter read once in a while, and he also read adventure books, but Darling still read the traditional princess stories which she considered boring. The librarian, Madam Grimm, recommended adventure, mystery and hero books to Dexter but quite the opposite to Darling. As soon as she left the household, Darling went to bed and found a book by her room's doorstep. It was the Secrets of Sherwood Forest book by Maid Marian.
- Chapter 15: Squire Darling to the Rescue
Darling calls in to check on Dexter and Hunter answers the phone for him, as he's still sick in bed. Because Hero Training is on Dexter's schedule that day, Darling decides on saving Dexter's reputation, by ruining it. How she will do it is by lowering the expectation bar because it was set too high for Dexter to ever meet the last time Darling jousted in his place.
At the time of Hero Training, Darling actually gets a perfect score and forgets about her plan of saving Dexter's reputation.
- Chapter 16: A Charming Confession
Darling enters Dexter's dorm room for an apology and confession of what happened earlier in Hero Training class. Before the two can talk any further, Hunter steps in and reports that King Charming is making his way to the dorm room. Once King Charming steps in, he claims to have come a day early because of his meetings. Although he is somewhat awestruck that Dexter was deemed best in class, he is looking forward to the best Charmings, Dexter and Daring, jousting against each other for the tournament. King Charming directs Darling and Hunter outside as he needs to speak with his son in private. Darling eavesdrops and overhears that he is going to make Dexter lose to keep Daring the reigning champion, because it is Dexter's destiny to be the second best. Now that Darling's got Dexter in quite the pickle, once King Charming leaves Darling apologizes and promises to make it right, however Dexter has had enough and no longer wants her to help him anymore. Hunter is quite suspicious as he hears this.
- Chapter 17: Questions and Crisps
Darling pretends to faint and Hunter and Dexter help her. Hunter expresses his suspicion on how Darling is to not ever wear Dexter's armor "again", signifying that she was probably impersonating him. Darling sheepishly turns down the fact and Hunter believes her, guessing he hit his head too hard in Hero Training. Hunter escorts Darling to Damsel-in-Distressing. In Damsel-in-Distressing class, Darling and the students watch a movie on how to be confident and have etiquette. After that, Darling makes he way back to the dorm room and steps out for a while to the Royal Common Room. There she meets Raven and they have a short talk about Raven's prince preference. Raven describes her perfect prince to be, trying not to offend Darling, someone the opposite of Daring. She makes a coincidentally similar description to Dexter. After that, Raven leaves because she has studying to do. Darling soon gets a text from Maid Marian, who asks for a rendezvous at the drawbridge, adding that she should bring her running shoes.
- Chapter 18: Marian by Moonlight
As soon as Darling and Maid Marian sneak out of the school premises, Darling asks what this meeting is about. Maid Marian simply says it's an adventure in the Enchanted Forest. There, Maid Marian pulls out a bow and arrow and Darling familiarizes herself with archery. After the first few tries, Darling catches on and is able to shoot a far distance. Maid Marian soon asks Darling about her goal, if she was really rebelling. Darling informs her that she wants to be a hero, but Maid Marian cautions her that people aren't considered heroes if their target doesn't need saving. That immediately makes Darling think of Dexter. Setting that thought aside, Maid Marian and Darling go running.
- Chapter 19: A Damsel Parade
It is finally Parents Weekend and the Royal students are eager for it to start. Some events on the day include a Damsel-in-Distressing class parade and a jousting tournament from Hero Training class. As soon as the Damsel parade comes to an end, the parents and students are on the edge of their seats as their jousting tournament is about to start. However, King Charming has clearly given out his orders to Hunter to escort Dexter to the tournament, and since he's Hunter Darling is sure that he would have executed his requests. But as a few knights made their way out, Dexter was still in the tent. Darling then slows down time and runs to find him.
- Chapter 20: The Knight in Dented Armor
As soon as Darling finds Dexter in the tent, she sees that he's doing much better with his princely pox and is almost healed, except he's upset not because of purposely losing for Daring's sake, but for his glasses in his helmet. Darling reassures Dexter that Sir Gallopad will help with his sense of direction and will guide him wherever. As the championship match between Daring and Dexter begins, Dexter is quite clueless as to how to use a lance, so he just improvises as he jousts. However, Darling slows down time so that she can reposition Dexter's lance to hit Daring's shield properly, but not squarely. After Daring is victorious, Darling considers the world back in order.
- Chapter 21: Happily Ever After
The students congratulate Daring for winning and Dexter for coming second place. Betty drives in and sees that she missed her chance of fixing Dexter's helmet and would like to make it up to Dexter. Darling soon runs into her mother, who gives her Maid Marian's work, Secrets of Sherwood Forest. Darling is surprised as Queen Charming cups her face and is glad that Darling is who she is. However, Darling notices that Queen Charming's hands felt rough when she touched her face, almost like she had calluses.
- Like in "Spring Unsprung", students are unaware of what a cassette tape is.