Moment subpages are Spoilers Off. You Have Been Warned
- The premise of the series is that the fairy tale characters' children are forced into their parents' roles, even if they don't want them or have befriended someone on the opposite side.
- "Sorry about earlier. You're the best daughter ever after." Can you even begin to imagine how hard it must be for Mr. Bad Wolf, Red Riding Hood, Cerise and Ramona, having to keep their secret from everyone?
- In Cerise's Picnic Panic, Cerise and Red have to act afraid of Badwolf in front of Hunter to keep the secret. He knows its an act, but Badwolf is still hurt by his wife and youngest child having to pretend to not know him, seeming tired of all of it.
- Sucks to be Raven Queen. Though she's used to it by now, no surprise in that she must have had one very depressing childhood.
- In Raven's Story, she remembers what her childhood was like when her mother was free: sitting on her mother's lap while she met with generals and hatched plots to conquer, kill and take control of other kingdoms, spending hours in the dungeon workshop helping to make toxic potions, spiked-armor soldiers filling the castle, odd creatures in the shadows that hissed at her...
- Raven on Legacy Day. She's clearly hesitant and terrified because she thinks if she doesn't sign the book and accept her fate there's a chance she'll disappear, only for the book to show her such a horrible fate (arrested, run out of town, homeless, chained up and screaming) that she realizes she can't sign anyway. Thankfully made so much sweeter when she realizes she's still there after not signing.
- And despite all of this, she still loves her mother. She may not be the most affectionate of parents, but she's got solid advice for when Raven really needs it.
- When Ashlynn tells Hunter they need to break up. Just the heartbroken look on his face...
- And then the misunderstanding between Raven and Dexter. Raven thinks she's too late and he's with Cupid (who's just comforting him for thinking he lost Raven to Daring) and then Dex goes to give her his heart favor only for Lizzie to snatch it up along with the others she's nabbing.
- Cupid. Just... Cupid. For the daughter of the God of Love, she has extremely bad luck with her own love life.
- It doesn't help that when she finds out Raven and Dexter's feeling for one another are mutual she tries to play matchmaker for them, giving up on her own feelings for Dexter.
- The reason Lizzie Hearts cultivates a reputation as an eager villain-to-be, despite her knowing her mother is nothing of the sort? She thinks that accepting a destiny as Ever After's caricature of the Queen of Hearts is a ticket back home to Wonderland.
- In the special "Way Too Wonderland", Lizzie Hearts finally gets to see her mother again...only for the Queen of Heartsnote to outright tell her that she hates her. It drives poor Lizzie to tears. Thankfully, the Queen mentions that she loves the "opposite game", causing Lizzie to realize what was really going on.
- In The Unfairest of Them All, Apple's attempts to get Raven to renege on her decision to Screw Destiny are just plain depressing. Made worse by the fact that Raven isn't really that happy with the consequences of the decision, either.
- Maddie frowning for the first time. The sheer weight of all the unfortunate series of events that led to her unjust expulsion hits straight home when she starts hopping away on one foot, to try and stay positive.
- Apple and Raven are completely lost in the wake of Legacy Day. Neither had anticipated the consequences, or know how to deal with them, and neither does anyone else. To anyone who's ever felt completely lost at what to do with their life, or had felt that way, it's a very powerful scene.
- A little worse in the Book, The Storybook of Legends, since Apple and Raven had just truly become friends and Ravens decision almost completely undoes it.
- "I love you!" and "I love you, too." said just before Raven smashes her mirror and prevents her mother's escape.
- And Raven brings up her mother's poisoning of Wonderland and hurting her best friend Maddie because of it as a reason she can't let her escape.
- Poor Red Riding Hood crying over her daughter's reveal to the Hoods and Wolfs Clans about her heritage.
- Cedar turning back to wood in the third book. Even the Narrator gets teary eyed.
- In the third book, the descriptions of how out-of-place Lizzie and the other Wonderlanders feel in Ever After where nothing makes sense to them and that they got so close to being able to go home.
- All three of them got their moments. Lizzie tries her hardest to follow all of her mothers advice, and in one moment, just wanted her mother to come and give her a hug. Remember her mother is completely off her rocker, and Wonderland is sealed off. Kitty actually had a chance to return, but didn't, and it's quite clear how hard this was for her to return to her friends and give up possibly her only chance to go back home. Maddie got to see her father sacrifice himself, then see the Jabberwock USE HIM AS A HAT. The book was tough on all three of them.
- Briar Beauty's destiny involves her sleeping for a hundred years. By the time she wakes up all of her friends will be long gone. This hits her especially hard in Thronecoming, where she rebels to the point of getting rid of the real Book of Legends so she doesn't have to sign it because she's so scared of her destiny.
- In Next Top Villain, Duchess ends up getting a lot of these: trying to deal with her destiny while all the other princesses (eventually) get Happily-Ever-Afters, Daring constantly brushing her off, having to choose between failing out of General Villainy and staying a Royal or becoming a Rebel and a villain (and maybe the next Evil Queen) so she can learn magic that will allow her to remain human, having to choose between betraying her friend's trust or passing the assignment that could lead to her being able to change her destiny, how horrible she feels after betraying Lizzie and how others are openly mean to her the next day because of what she did.
- Raven gets one too, when she explains to Duchess how she doesn't want to be a villain because she doesn't want people to hate and fear her, and how being a Rebel means having to deal with people looking down on you.
- In Cerise's diary, when fellow students start speculating about her and Mr Badwolf due to Blondie's Mirrorcast, she describes her throat closing, a common symptom of a panic attack and hides for hours in the dark Grimmnasium, crying. This, of course, evokes a massive My God, What Have I Done? reaction from Blondie.
