Just because this is a rather light-hearted and optimistic Fic compared to many other Frozen fanworks, doesn't mean that there are no genuinely sad moments.
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In General
- This fic, with its emphasis on relationships, really makes anytime those relationships are damaged come alive on the screen, and emotionally resonate quite well.
Specific Moments
- The first sad moment of the fic involves Rapunzel hearing about Anna and Elsa's backstory. Though the story itself was no sunshine, the real downer was where Rapunzel realized that even though Gothel lied to her all her life, at least Rapunzel had somebody. Now because of Elsa's powers, Elsa and Anna have nobody, so all she really wants is to be there for them so they can be together for the first time in forever.
- The Tangled crew briefly see Anna's Disney Death and Elsa cradling her frozen sister's body. This causes Rapunzel to break down in Eugene's arms as well. While not having personally known much about the two sisters, the scenario likely reminded her of Eugene's own near-death experience.
- Elsa's apology to Anna after their adventures are over. Elsa kept so much from Anna for so long, so when she finally let it all out how sorry she is for shutting her out for years on end, it really comes across as a genuine Tearjerker. Thankfully, it's also a heartwarming moment, because Anna forgives her afterwards.
- The Drama Bomb of chapter 10. When Kristoff reveals that Eugene was a thief, and Rapunzel's confession of once having magic, rifts begin to form between the humans. With Rapunzel devastated that Elsa won't forgive Eugene, Elsa guilty that she might've blown things with Anna with her sentencing, Anna angry at Kristoff for causing all this, and Elsa disappointed and hurt that her new friends lied to her about such big things.
- Elsa's desperate pleading to Anna not to be mad at her for what she did to Eugene. You can tell she's trying to put on a professional face, but when it comes to reconnecting to Anna, she'll do anything to keep her on a good side.
- The alley confrontation on Saturday. It's so sad to see how only a day before there was optimism and happiness, only for anger and mistrust have now formed between Rapunzel and the Arendelle sisters.
- Of particular not is the moment when Rapunzel screams, "I HATE YOU! I HATE ALL OF YOU!" Rapunzel is an extremely bighearted woman, and to see her scream out something like that really resonates with you.
- Especially since only a few moments later, Rapunzel has a My God, What Have I Done? moment, regretting that she would say such a thing to 2 people she considered friends before all this.
- Rapunzel crying with Olaf. It's an extremely touching situation, seeing the perpetually sunny princess sobbing into the arms of a snowman, lamenting that all that she hoped for on her honeymoon has gone wrong.
- The Sunday Tragedy. Simply put, no chapter was as tragic and sad as chapters 14 and 15 about day 8 of the honeymoon, and the day it all really went downhill for everyone.
- The day begins with optimism. Elsa is going to mass to be with her people, Rapunzel is still telling her story to Anna, and Eugene and Kristoff for the most part had buried the hatchet. And then it is revealed that Kristoff intended to play a mean prank on Eugene earlier in the day, but forgot about it, resulting in Eugene breaking his arm when the sleigh broke. Right away, Kristoff has a My God, What Have I Done?.
- Then when he gets back, Anna is at first in denial that Kristoff could possibly cause Eugene to get injured. However, the moment he reveals the truth to the Frozen crew, she goes into an Unstoppable Rage, slapping him over and over, upset that he could possibly do something so malicious. Olaf too is stunned by this, and Elsa, the one person who could stay sane during this reveal, can only look in sadness and horror at Anna unraveling before her eyes.
- However, all this pales in comparison to when they tell the Fitzherberts about this. For a moment, there's only Tranquil Fury from Rapunzel, just asking that they all leave. And then Eugene, who had previously tolerated Kristoff's earlier hostility with stride, snaps and wails on Kristoff, angry that he could possibly have done something to him like this. From there, it only gets worse.
- Rapunzel and Eugene, previously the unsurmountable couple, have a fallout with each other on how to react to this.
- Anna angrily compares Kristoff to Hans, and breaks up with him, prompting more arguing between them and the Tangled crew.
- Olaf. Sweet, optimistic, and wise Olaf can only look in horror, without any kind of wisdom to bring everyone back together.
- But Elsa has it worst. Seeing her whole "family" arguing among themselves, she goes into a Freak Out, withdrawing back into her own bad memories, before finally letting out a big STOP that finally gets everyone to stop. She then flees to her own room, trying to get a hold of herself, only to discover her panic attack caused her hair to become undone, and that all the repairs to the castle she did before were destroyed in her moment of lost self control. She fixed it, but to see practically her whole world come crashing down like that is not an easy read at all.
- Then Anna finds out that Kristoff left out of guilt for what happened, and runs to Elsa, weeping that she can't make up with him after all this. And despite her new resolve to help Elsa reconnect with their kingdom, she's still a sniveling wreck.
- Then Elsa sings a reprise of "Do you Want to Build a Snowman", falling asleep out of exhaustion and sadness. Thankfully, there's also a good heartwarming moment there with Anna giving Elsa a sleeping hug after their bad day.
- Then there's Rapunzel witnessing Kristoff leave Arendelle. Part of her really wanted to be angry with him, but seeing him so broken from all this, actually is a little sad, especially in how she can't ever bring herself to hate him enough to want him dead.
- Rapunzel, after having a bad dream about Eugene freezing and falling to pieces, wants nothing more to do with either sister, and even considers leaving Arendelle. Considering all the joy and optimism she had going into this honeymoon, it's rather sad to see her change her tune so drastically.
- When Anna finds out that Kristoff is missing, she breaks down in Rapunzel's arms, sobbing that she's sorry for being so hostile to her the day before, and lamenting It's All My Fault because of her breaking up with him. Worse, she withdraws into herself afterwards, just about tuning everyone out for her guilt.
- Rapunzel completes creating a Broken Pedestal for Mother Gothel once she found out the origin of her powers. The raw betrayal in her voice when she realized that Gothel probably only loved her hair is very well written. Anna, despite having suffered a similar betrayal by Hans, was at a loss for words and not sure how to comfort her.
- When Elsa struggles with her training to control her powers, she briefly rails on the portrait of her parents, blaming them for the trouble that they had unwittingly caused by separating her and Anna. It's pretty sad in that their parents, despite their best intentions, only ended up causing more trouble.
