sae or asuko he/it. i like lost in the clouds, orv, yttd, hetalia, danganronpa, the summer hikaru died, pokemon, project sekai, enstars, superfish, soul eater, mystic messanger and twisted wonderland

this is unfinished dont ounch me owwww oww oww

⬇️⬇ i had this idea for weeks because of twitter and a analysis i saw! but it came to me again at like 6:10pm on august 7th cause of my discord status and oomf appreciation of my love for riddle

Riddle Analysis Thread:
TOC:

• Overview
• Basic Information
• References
• Personality
• Backstory
• Relationships

Riddle Rosehearts is a 17-year-old (no longer 17, as of Book 8 so he'd be about 18) second-year (sophomore) student at Night Raven College and the housewarden of Heartslabyul. He is 160 cm (5’3”) tall, born on August 24, and comes from the Queendom of Roses. Riddle is a top student with a particular aptitude for Practical Magic, and he is known for being exceptionally skilled at magic for his age. He is in Class E (No. 26) and also a member of the Equestrian Club, with Silver and Sebek. Outside of academics and magic, Riddle enjoys caring for hedgehogs, solving crossword puzzles quickly, and eating strawberry tarts. His greatest pet peeve is rulebreaking, and he doesn't like junk food.

Riddle's character is heavily centered around control, perfectonism, authority, and repression, but what makes him so interesting to me is he got these traits from somewhere. His upbringing shaped parts of his personality, while also preventing him from developing like a normal child could.

Riddle is described to be "serious-minded" and a top student, while also being strict with himself, which is shown on several occassions.

Riddle grew up with both of his parents, who are both implied to be doctors in magic, and his father, who remains unnamed being invisible for most of this life. This can be seen in one of Riddle's voicelines, where he mentions how the "Queen of Hearts" had a good marriage, but his parents never had that aspect. His mother in particular was extremely accomplished and held him to very high standards. From a young age, his life was basically structured around academics and meeting her expectations. What he ate, what he wore, when he studied, how much free time he had, and even who he was allowed to spend time with were all heavily controlled.

Riddle learned very early that being obedient, intelligent, and “correct” was what made him worthy of approval. Whenever he failed to meet those expectations, his already limited free time would be taken away and he would be pushed even harder. This is shown post-Overblot when Riddle's mother scolds him for requesting a sugary treat instead of her necessiaties.

Riddle’s relationship with rules becomes REALLY important, because he isn't simply taught just "follow rules because I said so.” He was raised in an environment where rules basically dictated his entire life. He had very little opportunity to develop his own sense of what he wanted, what he enjoyed, or even what was okay for him to do.

In Book 7, his dream is set around and how it shows a glimpse of Riddle if he was allowed to experience what it was like to be a child. Riddle is still demanding, but he has eased it down because he doesn't have the burden of expectations on his shoulder. Riddle’s strictness isn’t his entire personality. It’s something that developed around his personality. His actual childhood taught him to suppress his wants in favor of what was “correct.” His dream shows what happens when that suppression isn’t imposed on him.

Relationship with Trey & Chenya: Trey and Chenya met him while he was studying, invited him to play, and Riddle begins sneaking out during his study time to play with them. His mother eventually discovered this and forbade him from playing with them. However, many years later, they are still friends and visit eachother from time to time, despite Chenya being in a rivaling school.

Trey and Chenya were basically an escape from that environment at home. They introduced Riddle to ordinary childhood experiences like playing together and eating tarts like he always wanted to do. Since Trey has known Riddle for a long time, he knows how Riddle acted before becoming Heartslaybul's housewarden, his relationship with his mother, his tendency to push himself too hard & how he still wants affection and approval even under his facade.

I'd like to mention this as well, I do not think Riddle should be babied for his actions, he had it rough, yes, but many people were hurt from his unjust rules, and this behavior would've continued; had it not been for Ace, who wasn't afraid of backing down from his Housewarden.

However, Trey doesn’t actually agree with Riddle’s authoritarian behavior. He’s frequently the one who pushes back against him or tries to get him to loosen up. But because Trey knows Riddle so well, he feels unable to approach him when it comes to telling him he's taking things too far.

Trey himself recognizes that he had opportunities to intervene. He knew Riddle from childhood, understood what Riddle’s mother was like, and knew that Riddle’s behavior wasn’t normal. Yet for a long time, Trey chose to placate him rather than directly challenge him.

That becomes especially important in Book 1 when Ace essentially calls Trey out for letting Riddle get away with everything.

Trey’s reasoning is complicated: he’s accustomed to Riddle’s behavior, he knows Riddle’s history, and he doesn’t want to make things worse. But that compassion also becomes a form of enabling. Trey understands Riddle better than almost anyone, but understanding him doesn’t mean he always does what’s best for him.

By constantly smoothing things over, he also helps maintain the environment where Riddle doesn’t have to confront the consequences of his behavior. Trey isn’t malicious, neither is he secretly manipulating Riddle. He genuinely cares about him, but he’s also conflict-avoidant, and viewed Riddle calm is easier than actually confronting him.

This is not slandering Trey, almost everyone around Riddle refuses to challenge him as they are afraid of the consequences of being disobedient so they are all guilty by association. Trey does it, Cater does it, the Heartslabyul students do it. Even Chenya, who knew Riddle before NRC and knew what his home life was like, doesn’t simply walk up and tell him he’s being unreasonable.