Riddle and Rules

When Azul asks Riddle if he would let an enemy hit him if it were written in a manual, Riddle responds, “I’d do so if it were a rule.” 

Riddle’s strict adherence to rules seems to have come from his upbringing, where every minute of his life was planned by his parents.

Trey explains, “Riddle sees the enforcement of strict rules as a service to his dorm members. In his eyes, being bound by rigid guidelines—by fear—is a fast-track to personal growth. Because that’s how it worked for him. And on the flip side, he sees the violation of those rules as an inexcusable offense.”

Later in Book 1 Riddle quotes his mother, saying, “A man who cannot follow rules is a man who cannot achieve anything.”

When Deuce agrees that rules should be followed but calls Riddle out on his methods Riddle responds, “Then you agree that breaking rules is wrong. And in this dorm, I AM the rules. Therefore, those who cannot abide by my decisions deserve not the heads they use to complain!…My mother was right! And that means I’m right too!”

After his overblot Riddle asks his mother, “Why does my heart hurt so much?,” and, “What rule do I need to follow to make this pain go away?”

In the aftermath of his overblot Riddle is still strict, but when he claims he has “become much more lenient about enforcing the rules,” Cater agrees.

In Riddle’s dream of Book 7 he is a singer in a two-person band who holds street performances without receiving permits and curses and police (Ace: “I can’t believe our housewarden actually knows those words…”),

Riddle invites the group from NRC to join his and Chenya’s band, saying, “It’ll be mad and chaotic like never before!”

Idia reassures the group that “Riddle’s memories haven’t been completely erased. They’re just stored somewhere, and there should be a way to pull them out,” and we possibly see an example of this when Riddle declares, “No private side conversations at my tea parties!”

When Cater describes Riddle as he is in the real world by saying he is “super stringent about rules. He practically personifies the ideas of strictness and discipline,” Riddle responds, “Who would willingly let themselves get tied down by rules? Not me! Rules just suck the fun out of things. I’m sure your housewarden is as joyless and unpleasant as they come.”

Deuce takes offense, saying, “Even if this is a dream, it’s like he’s invalidating himself…!”

Riddle continues with, “I feel bad for you people having to live with someone like that.”

When Riddle nearly awakens he is coaxed into remaining asleep by darkness versions of Heartslabyul students who say that they understand he is only being strict for their own benefit (“You helped me discover that upholding the rules is my purpose in life!”) while a darkness version of Trey assures him, “Everyone here is grateful to you.”

In Book 1 Ace presents Riddle with a chestnut tart that, in accordance with the rules, he orders be destroyed. He will also reference the rule “One must leave the table within fifteen minutes of completing their lunch.”

Both before and after his overblot he enforces the rule “The post-meal beverage is to be lemon tea with two sugar cubes,” but at the end of Book 1 he admits he wanted to eat the chestnut tart, he prefers honey to sugar cubes in his tea (“and I like milk tea better than lemon tea anyhow”), and he wants to sit and talk with everyone after a meal.

In Riddle’s dream of Book 7 he presents his guests with cups of tea with five sugar cubes and “lots of milk and honey.”

Riddle seems to struggle with cooking due to the amount of instinct that is required (“I specifically asked you to stay quantitative. Can one really make good food on instinct alone?”), saying, “For me cooking has always meant deciding what to make, then gathering ingredients and following a recipe step by step,” so he may interpret recipes as a form of rules, which he tries to follow to the letter:

When Riddle’s recipe during Master Chef does not specify cabbage-leaf size and the leaves themselves are of different thicknesses Riddle considers cutting them into squares and weighing them by grams. When the recipe does not specify how much water he needs for parboiling, he goes to a Ghost Chef for assistance. 

When instructed to mince meat to a width of 1 to 2 millimeters he tries to measure size exactly with a ruler. The chef stops him from doing so and also does not let him separate fillings into equal portions (Riddle: “I’m not completely happy with this.”)

At the end of Book 1 Riddle presents a strawberry tart made with oyster sauce (“I followed the rules exactly, and measured everything precisely!”), not realizing that Trey’s assurance that it was a “secret ingredient” in all tarts was a joke.

When asked what dorm he would transfer to Riddle responds, “the mirror’s selection is always right. I never even considered transferring to another dorm,” but he concedes to respond because “rules must be followed.”

Azul and Riddle clash during the descent into Tartarus where Azul is not pleased by how Riddle insists upon protecting him, but Riddle explains he is only protecting the rules: it is illegal for anyone to perform first-aid on those under the effects of transformation potions, like Azul, and tending to any injures he gets would “risk running afoul of the law. And that must be avoided at all costs!”

Similarly, when Idia thanks the other students for saving him from Eliza during the Ghost Marriage event, Riddle responds, “I was doing it because of the rules and to get classes started back up. I wasn’t really doing it for you…”

When Night Raven College is invaded by CHARON at the start of Book 6 Riddle approaches them by asking, “Did you obtain permission from the proper channels when you came onto campus?” When he does not receive a response, he declares them in “serious violation of the rules” and grants the Equestrian Club permission to use magic on the intruders.

In the battle against an oveblotted Idia Riddle refuses to drive the Chariot vehicle they have been provided as he does not have a driver’s license (“Then again, this IS private property. Maybe I don’t have to worry about that…In hindsight, I should’ve taken driving lessons and gotten a technomantic vehicle license”).

Azul balks at Riddle’s declaration that they are to use their magic to make up for the lack of energy within the Thunder Spear, and Riddle responds, “Did the manual say we couldn’t use other power sources? No, it did not!”

In Book 7.5 Riddle refuses to correct Savanaclaw’s form for the inter-scholastic tournament as “it’s prohibited for anyone other than the corresponding housewarden to revise or amend these documents.” Jade reflects, “I can see why the headmage placed Riddle in charge of collecting forms.”

Riddle assists Jade in refusing to allow Kalim an exception to the budget during Halloween, saying, “Scarabia is not exempt from the rules.”

On the subject of dancing Riddle says he is “more comfortable with dance routines that have set steps, rather than more liberal forms where you just move your body to the rhythm.” He says he has practiced ballroom and party dancing and he is reluctant to join “some sort of festival dance” that he doesn’t know the steps to during the Eternity Float event saying, “’Having fun dancing as I see fit’ is too much of a challenge for me.” 

Riddle dances with Kalim during Spectral Soiree and is caught off guard when Kalim suddenly changes the steps.

One of Riddle’s earliest lines to Grim is saying, “I will abide no rule-breaking,” and Grim talks about Riddle getting “all hung up on his dorm rules” during a Founding Day party due to the non-birthday-related party having no black tea.

Riddle will often mention rules in his dialogue, saying, “Everyone must enjoy themselves on Halloween. That’s the rule,” that it is a rule in Heartslabyul to always return what one borrows, that he must prune roses in accordance with the rules, and that, during the prologue, all he did was “adhere to the rules, as should be expected.”

During Glorious Masquerade Riddle says that Malleus has no reason to feel guilty about being the bait for Rollo’s plot as he has broken no rules, and he tells Ace, “I know how to recognize exceptional talent when I see it. Provided it’s a rule-abiding talent.”

Riddle scolds Floyd for running in the library (“It may not be one of the queen’s laws, but it is still very much against the rules”), tells Ace to ensure that his tsum “doesn’t break the rules in any way,” refuses to allow Sebek to excuse himself from Vargas Camp (“Rules are meant to be followed”) and reminds Idia that “the rules state that the researcher must be on stage in person” for Idia’s culture festival presentation.

When Grim greets Riddle as “Ragin’ Riddle” in Book 2 Riddle responds, “I am not ‘raging.’ I will be perfectly pleasant if you obey the rules!”

During Book 5 Riddle says he is will “have to be on constant lookout for fights and rule violations,” and reminds Deuce of a rule that states “a tea party must be held in the garden five days out of every month!”

Riddle says “Students of Heartslabyul must strictly adhere to living in accordance with our rules,” and Deuce has a voice line of, “The rules at Heartslabyul are very strict, but a lot of them are for our own good…probably.”

Riddle is confident that his Equestrian Club look complies with all the numerous rules governing competition uniforms but he is less certain about his second birthday look, asking if he is wearing it correctly according to the rules.

Trey explains that, to Riddle, “being bound by rigid guidelines—by fear—is a fast-track to personal growth,” so living in fear of punishment is possibly something Riddle grew up with, and might believe to be normal.

Riddle says, “If there were no penalties, no one would follow the rules,” and he tells Leona that he is is happy in his dream of Book 7 because the illusions of his own making “genuinely fear me, and love him.”

When the darkness of Riddle’s dream protests against his punishments he threatens them with worse, forcing their acquiescence. Riddle says, “Ruling through discipline and fear is how order is upheld. Mother was right… I was right!”

When Riddle nearly awakens darkness version of Deuce and Ace assure him, “You’re only being strict for our benefit. We all understand that!”

During Port Fest Riddle assembles all members of his group to locate dropped change. When Riddle threatens them with “I trust you all know what will happen if we do not, yes?,” they respond “Not the collar again!,” and “I had enough of that LAST time!,” possibly illustrating Riddle’s system of enforcing order through fear of punishment.

During his birthday interview Riddle tells Idia, “You’ll need to give a proper answer or face the consequences,” and after hearing a story from Jade’s childhood he says, “It would hardly be a wonder if you had received a harsh punishment.” Georgina responds, “My, you must come from a strict family, Riddle.”

When Silver tells a story about falling asleep while cooking with a wood-burning fire Riddle asks if he received “a stern talking-to,” and when Trey tells Ace that working together builds unity Ace responds, “if by ‘unity,’ you mean we’re all unified in our fear of the housewarden yelling ‘Off With Your Heads!’”

When students try to start a fight during Book 5 Riddle collars them with his unique magic, saying, “This is your punishment for besmirching the dignity of Night Raven College.”

In a conversation with Jade he says, “Anyone who breaks a contract should be punished, and swiftly.”

During the NBC event Riddle orders Lock, Shock and Barrel to ta with his group. When asked why he responds, “Because you broke the rules. This is the consequence of your own ill-advised actions.”

Riddle enforcing his authority through fear of punishment is a theme of the Lantern event, where he questions if the students of Heartslabyul will be willing to go to the effort of freeing the group from the library unless they are afraid of what will happen to them if they don’t.

Riddle decides to threaten the dorm’s students via a dorm-wide email in order to ensure their compliance but he is stopped by Deuce.

Kalim and Jack try to assure him that the students will do as they’ve been told, but Riddle quietly says, “I question whether anyone there would act without the threat of punishment hanging over their head. I’m grateful to my mother…and that’s exactly why I’m so worried about the lanterns. Will everyone do their part without me watching over them? Without any threat of punishment?”

Back at the dorm the students of Heartslabyul seem to be just as reluctant to put in the work as Riddle had feared, saying, “it’d be nice not having someone constantly breathing down our necks about the rules for once,” but in the end they make the most lanterns out of all the dorms. Riddle reflects, “They all came together without any threat of punishment. Perhaps it’s because of my strict guidance. Perhaps everyone fell in line because they know I’m right. But…what if there was some other reason…?”

Riddle has memorized all 810 of the rules of the Queen of Hearts and is shocked when Ace says that “Laypeople aren’t gonna know the rules,” saying, “Not know the rules?! Of such an esteemed house? I don’t expect everyone to know all 810 rules by heart, but people should know at least a hundred of them. At LEAST.”  

When Idia refers to the rules as “nonsense” Riddle is not pleased, saying, “They’re the embodiment of my dorm’s law and order! If you insult them, I’ll have your head!”

Riddle is often reciting to the rules by number, including:
・Rule 1- “You must run at top speed forever and always to remain in the same spot.”
・Rule 23- “One must never bring a cat to a formal affair.”
・Rule 53- “When something is stolen from you, you must take it back!”
・Rule 89- “Never eat a tart before the queen without the queen’s permission.”
・Rule 124- “When you get soaking wet, you must dry off with a run in the ocean!”
(When Jade describes Riddle’s running to dry off he says, “He kept jumping all around while singing some nigh-incomprehensible song about spinning and twirling,” so it is possible there are additional details to this or a related rule that have not been shared.)

・Rule 53-  Riddle says. “In accordance with rule 153, I’ll have to make herbal tea instead,” but the exact wording of this rule has possibly yet to be revealed.
・Rule 228- “Flowers in gardens must never be picked on Wednesdays”
・Rule 249- “Flamingo caretakers are to don pink attire.”
(When his tsum tackles a student for being in violation of this rule Riddle says, “It’s certainly not okay to make their jobs more difficult…It’s always admirable to uphold the rules, but this tsum’s methods leave much to be desired.” He does not seem to notice any irony in this situation.)

・Rule 271- “One must leave the table within fifteen minutes of completing their lunch.”
・Rule 339- “The post-meal beverage is to be lemon tea with two sugar cubes.”
・Rule 346- “Croquet must not be played after 5:00 p.m.”
・Rule 413- “When you see a pair of moving glasses in the forest, never go back the way you came.”
・Rule 434- “If you see a caterpillar exactly seven centimeters high, you must recite a poem to its discoverer.”
・Rule 529- “If you eat steak on the night of a full moon, a cat must play the violin afterwards.”
・Rule 562- “One must never bring a chestnut tart to an unbirthday tea party.”
・Rule 703- “Anyone who comes in second in a croquet tournament must serve the queen tea the next day.”

There has been at least one unnumbered rule: Riddle quotes, “”When holding a meeting to determine prizes for a croquet tournament, the records of the proceedings must be written in blue ink,” but does not seem to reference which rule it is exactly.

In a vignette Riddle rejects an Unbirthday Cake for not having candles in it, rendering it “not in compliance with the Queen of Hearts’s rules,” but we have maybe not heard details on what exactly the rules about Unbirthday Cakes entail. 

During an event Riddle approves of the purchase of a food processor for the dorm, as, “If a food processor will make it easier to adhere to the Queen of Heart’s rules, then it’ll be worth it in the long run.”

All known rules have been compiled here ▶︎

Riddle seems to prefer adhering to only the letter of the law and will allow loopholes, such as when they provide a cat beast-person with a violin that they might not know how to play in order to not violate rule 529, “If you eat steak on the night of a full moon, a cat must play the violin afterwards.” (Trey: “There’s no stipulation in the rules about what song they have to play or how well, so it still counts.”)

Riddle does not stop Grim from stealing food in front of him during Port Fest (“He’s doing a taste test as part of the food stand inspection, isn’t he? I’ll allow it”) and he overlooks the violation of school rule #6, “”No fighting on campus,” in exchange for the information that the fight resulted in.

After the drama caused by Savanaclaw in Book 2 Riddle says, “Normally, I would demand their heads.

But if Trey and the others insist on settling their grudges on the field, 1 am willing to overlook their disregard for the rules this once.”

When Ace and Deuce volunteer to play for team Ramshackle during the exhibition match Riddle points out that they are members of Heartslabyul, but when Ace says, “There’s no tournament rule that says we can’t play for another dorm’s team,” he allows it.

When Trein asks Riddle to send an object from insight the library out through the window Riddle balks at the idea of breaking library rules. When Trein points out that the object is not library property and thus does not count as a rule violation, Riddle concedes.

Later, however, despite how the faculty give the students special permission to eat inside the library Riddle refuses to do so. As putting jam on cookies does not involve eating or drinking, however, he allows himself to do so, telling Jack about “a certain rule that states you have to put rose jam on scones at tea parties…”

After earning their freedom from the library Riddle initially refuses to use the window, their only exit, until they receive permission from the faculty, as Crowley has ordered them not to use the window to leave. Riddle eventually agrees to help the others leave but then refuses to follow after them, 

Deuce tries to convince Riddle to leave by pointing out that, if he stays, he will be in violation of one of the Queen’s rules (as Trey took second place in a croquet game, he must serve Riddle black tea).

Riddle tells Deuce to call Trey over so that he will not have to leave but Jack says he will do everything he can to stop him, accusing Riddle of using the rules as an acute to give up. Deuce tells him, “Upholding the rules means coming out of the library and helping us finish everything we have to do,” and Riddle agrees:

“I am the housewarden of Heartslabyul, the dorm based on the Queen of Hearts’s spirit of strictness. Breaking any Heartslabyul rule is unacceptable for someone in my position. And there is technically no school regulation against leaving through a library window. As long as there’s no written rule prohibiting it, our dorm rules must take precedence over a verbal commitment.”

It is then revealed that Riddle’s issue was possibly less about defying Crowley and more about defying his mother, as he had been determined to never jump out a window again: the last time he did so, she caught him playing with Trey and Chenya. 

Ultimately Riddle does leave the library through the window, and at the conclusion of the event he declares, “As housewarden of Heartslabyul, I must adhere to the rules. That’s the whole reason I took the plunge into the outside world.”