Rapunzel recalls how she and Cassandra first became friends.
Tropes in this episode:
- Aloof Ally: Cassandra insists being The Stoic Deadpan Snarker and makes perfectly clear to Rapunzel that as her Lady-In-Waiting she has to work with Rapunzel, but Cassandra does not want to be her friend. It's not until Rapunzel admits that she was trying too hard to have a human friend that Cassandra tries to be Rapunzel’s First Friend.
- Book Ends: The episode starts and ends with Cassandra talking to the mysterious child.
- Character Development: At first, Rapunzel reacts to every difficult situation as a Stepford Smiler. After Cassandra agrees to be Rapunzel's First Friend, and The Queen of Ingvarr reveals the Plot-Mandated Friendship Failure, Rapunzel Took a Level in Jerkass and reacts exactly as The Stoic Deadpan Snarker Aloof Ally Cassandra has been acting all the time.
- Comically Missing the Point: Rapunzel thinks that Cassandra doesn't want the hodgepodge statue of them both because it's "too big", rather than the fact that it comes on a little too strong.
- Disney Creatures of the Farce: One of the events in the princess games is befriending forest animals. The other princesses come out with the expected fare. Cassandra and Rapunzel return with two raccoons and wolf, respectively.
- Freeze-Frame Bonus: One of the previous winning teams is "Princess Arianna and Princess Willow."
- Freudian Excuse:
- The entirety of the flashback is Rapunzel explaining to Eugene why she's stubborn and adamant about hiring someone like Cassandra rather than giving her new handmaiden ("the dud") a chance.
- In the flashback, Rapunzel explains to Eugene that the reason she wants to befriend her distant handmaiden Cassandra is because she's forthright, as opposed to Gothel who lied to Rapunzel for years.
- Friend-or-Idol Decision: In the flashback, Cassandra had a choice between succeeding at the Contest of the Crowns (which would win her a place in the Ingarr Battalion, but also leave behind Rapunzel) or deliberately lose the contest (a show of how much her friendship with Rapunzel means, even at the cost of her dream). One can figure out which she ultimately chose.
- Hidden Disdain Reveal: Cassandra has been polite enough to drop hints that she does NOT want to be Rapunzel's friend, but after Rapunzel was trying too hard to be her friend, Cassandra blows up:Why can't you understand? We are not friends. I don't like dumb dance moves or friendship bracelets or sleepovers, my idea of having fun is not having fun. Good night.
- Heel Realization: In the present, Rapunzel realizes just how much Cassandra's always sacrificed her ambitions for the sake of their friendship, and feels guilty she didn't do much to repay her.
- Hope Spot: At the end, Rapunzel still has hope that Cassandra is still that friend from the day they met. In the next scene, Cassandra's hatred for Rapunzel grows more when the mysterious child reveals Rapunzel still has some of the moonstone's power, as demonstrated by the tearing of the picture of her and Rapunzel.
- Hypocrite: In the film, Rapunzel roused up the Snuggly Duckling Thugs to be true to themselves and follow their dreams no matter what everyone else thinks. Here, she tries to conform lady-in-waiting applicants to be exactly like Cassandra, which only freaks them out.
- Rapunzel also realizes that in hindsight, it was also hypocritical of her to somewhat discourage Cassandra to give up on her dreams, even for the sake of their friendship.
- Ironic Echo: "Winners focus on winning, remember?" The first time, Cass says this to Rapunzel to get her to take the competition seriously. Later, it's used by Rapunzel to rub it in to Cassandra how hurt she made her feel.
- Ironic Echo Cut: When Eugene said she should give the new lady-in-waiting time like she did with Cassandra, Rapunzel insists that she and Cass got along the day they first met. We flashback to a dissatisfied Cass complaining about Rapunzel.
- Irony: In the flashback, Rapunzel wanted Cassandra for her handmaiden and friend because she wanted to distance herself from someone like Mother Gothel, unaware at the time Cass was related to her.
- Like Father, Unlike Son: Rapunzel describes that the reason she likes Cassandra is because she's painfully honest with how she doesn't like Rapunzel, as opposed to Gothel who lied to her face for 18 years and showered her with false assurances of love. In hindsight, Rapunzel was making a statement of how Cassandra turned out rather differently from her birth mother (at least before her Heel–Face Turn).
- Misplaced Wildlife: As with Ruddiger, you wouldn't find Raccoons in Europe during Rapunzel's time, and yet they're seen amongst other woodland creatures here.
- My God, What Have I Done?: Given her Dark and Troubled Past, Cassandra does not realize she is being a Manipulative Bastard until she sees Rapunzel has Took a Level in Jerkass and she reacts exactly as The Stoic Deadpan Snarker Aloof Ally Cassandra has been acting all the time. This realization is enough to trigger Cassandra's Jerkass Realization and Friend-or-Idol Decision.
- Mood Whiplash: Again, after the final dramatic scene with Cass complete with an ominous theme, it immediately cuts right to the happy ending theme.
- Non-Standard Character Design: The raccoons that Cassandra finds look vastly different from Ruddiger, appearing more realistic in contrast to Ruddiger's more cartoonish look.
- Nostalgia Filter: Rapunzel recalls that when she first met Cassandra, they became friends almost instantly. The flashback says otherwise when we cut to past Cassandra complaining about Rapunzel, indicating the "we got along right away" viewpoint is only one-sided.
- Pet the Dog: Part of what endeared Rapunzel to Cassandra. When the latter found a rat in a suit of armor, she didn't scream or panic or try to kill it. Instead, she safely took it outside and even gave it a tiny crumb of cheese.
- Plot-Mandated Friendship Failure: Rapunzel's trust in Cassandra is crushed when she learns she only joined her in the Contest of the Crowns so she could impress the Queen of Ingvarr's battalion and leave behind her duty as a lady-in-waiting.
- Replacement Goldfish: As Eugene lampshades, it's pretty transparent that Rapunzel isn't really trying to find a new lady-in-waiting, but rather someone just like Cassandra.
- Rapunzel does not realize it, but Cassandra reminds her of Mother Gothel because she is her daughter. Cassandra is the dream of every abused child: A relationship with a Parent that is not abusive.
- The Reveal: The mysterious child reveals that Rapunzel was given a fraction of the moonstone's power when she first touched the black rocks, in order to protect the sundrop on her way to the Dark Kingdom.
- Symbolically Broken Object: At the end of the episode, Cassandra tears apart the picture of her and Rapunzel, once again demonstrating that they are not friends anymore.
- Trrrilling Rrrs: How the kingdom of Ingvarr's name is always pronounced.
- What You Are in the Dark: Without knowing that Rapunzel (and Pascal) were watching her, Cassandra took the time to take the rat she found and safely bring it outside out of simple kindness. This was what convinced Rapunzel that Cass was someone worth befriending.
- Whole Episode Flashback: Most of the episode is a flashback to Rapunzel's early days in Corona with Cassandra.
