Riddle, Being Housewarden

When asked if he has any treasures that he guards closely Riddle says he has something he’s prefer people generally not see: his housewarden’s log.

Riddle explains, “In addition to recording housewarden meetings and duties, it also contains information related to students, so any leaks would be unacceptable.”

Riddle says, “Recording every bit of minutiae is handy for understanding and managing dorm affairs. But lately I’ve been writing an increasing amount. I suppose that could be chalked up to more things worth writing about…”

When asked what he writes about Riddle mentions Ace and Deuce’s arguments and trouble at Unbirthday Parties, saying, “I never imagined how staggeringly eventful the days could be when I first became housewarden…and with more to write about daily, I have to replace my notebooks more frequently.”

Rook says that Riddle’s log sounds more like a diary.

Riddle became Housewarden of Heartslabyul “before the end of his very first week at school” by challenging the previous housewarden to a duel for leadership of the dorm, and winning. As housewarden, he participated in the Arcane Academy Interscholastic Games in his first year.

Trey says that it “caused quite a commotion” when Riddle became Housewarden, and in a flashback we see that one of the first thing he did was declare that all students were to memorize all 810 of the Queen’s rules.

In addition to having the students memorize the rules he also strongly enforced them, citing the fact that no student from Heartsalbyul dropped out or was held back since he became housewarden, that they are the only dorm that has achieved such, and that he has the best academic standing as proof that he is the “most correct” and out to be obeyed without question.

Riddle says, “It’s not off with their heads because */* want to do that. I do it because rules must never be broken,” and “Do you think I enjoy having to do this? You’re the one who broke the rules. As much as I would like to, I cannot ignore these infractions. It’s for your own sake,” in line with what Trey explains about Riddle’s childhood: raised with every minute of his day planned out, he came to see the enforcement of rules as a service to the members of his dorm.

Riddle dreams of enforcing the Queen’s rules upon the students of Heartslabyul in his usual same manner in Book 7, but instead of rising against him as they do in reality, the students are grateful for his efforts.

Riddle expresses reluctance to go along with Jade the start of the Eternity Float event, and Jade responds, “What I’m asking is whether or not you’re going, and, by extension, whether Heartslabyul’s housewarden honors his commitments.” This successfully convinces Riddle to attend. 

Riddle will often remind others of his position in conversation, repeatedly declaring that he will do things “as Housewarden of Heartslabyul.”

Riddle says “A housewarden must always be a model to their dorm’s students” and he seems to take on many tasks that he sees as his responsibility as Housewarden, telling Deuce, “It’s my duty as housewarden to resolve the woes of those living under my supervision,” and saying, “As long as l am housewarden of Heartslabyul, I will not allow any of my students to fail.”

In a vignette Riddle says, “Any self-respecting housewarden should be capable of resolving his dorm members’ problems, regardless of what year they are.”

Riddle volunteers for the Ghost Marriage event first because “it would be a dereliction of my duty to dispatch my vice housewarden while I sit on the sidelines,” and again later—after Trey and Deuce fail—because “A housewarden’s job is to make up for the shortcomings of his dorm’s students.”

Riddle also volunteers to serve as bait for firelotuses during Glorious Masquerade, as “even the Queen of Hearts took the field in battle to punish a major rulebreaker. I am the housewarden of Heartslabyul. It’s only natural that I would follow Her Majesty’s example.”

When Trey catches a cold in a vignette Riddle says, “If I don’t do something to help, my competence as Housewarden will be called into question,” and his wish for the Starsending event is “for Heartslabyul to soundly crush the other dorms with our scores on the next exams.” When Trey asks if he will not wish for good grades for himself Riddle responds, “It’s the least a housewarden can do. Besides, I hardly need it for MY grades.”

Riddle tells Malleus, “The Heartslabyul housewarden is expected to show initiative during campus emergencies,” and he refuses to participate in the Fairy Gala event because “It wouldn’t do for a housewarden to be absent from their dorm during an emergency. I must safeguard my dormmates.”

Riddle says “Improving a dorm’s quality of life is a housewarden’s job,” during the first NBC event he says, “With this many housewardens around, we can hardly let fellow students go missing on our watch,” and he later tells Idia, “A housewarden should serve as a shining example to other students.”

Riddle says that, as Housewarden, he can “of course recite each and every one of the Queen’s rules,” and after being kidnapped to STYX in Book 6 he says, “as Heartslabyul housewarden, it falls to me to uphold the rules wherever I can,” while during the battle against Malleus he tells Deuce, “If we are to charge, it only makes sense for the housewarden to lead the way.

After asking Idia why it is that Idia summoned him and not Ortho to help with the technomantic programming of barriers to keep out Malleus in Book 7—something the Riddle has never done before—he learns that Idia prioritized the safety of the group that needs Ortho to guide their way through the dreams, which include students from Heartslabyul. Riddle then declares, “If that’s the case, I owe you a debt as housewarden of Heartslabyul. 1, Riddle Rosehearts, housewarden of Heartslabyul, hereby accept the duty of fending off Malleus!”

Both Riddle and Cater thank Riddle for his efforts towards the end of Book 7 and Riddle responds, “I merely did what would be expected of any housewarden. It’s hardly worthy of such praise.”

After compromising the final group’s plan to deceive Eliza by losing his temper at a ghost guard Riddle insists on taking responsibility for his mistake by fending off a regiment of ghosts on his own, sending the rest of the students on ahead without him. During Book 6 Riddle assures STX staffers, “We’ve all been trained by our school as first responders in the event of an emergency,” but it is a little unclear if first-responder training is a mandatory part of being a housewarden and/or vice-housewarden at NRC.

While the Fairy Gala IF group includes students who are not members of Heartslabyul, Riddle brings food for the entire group during the event after Ace and Deuce do not show up for dinner. 

After the group’s plan fails Riddle says, “I take full responsibility for entrusting them with such an important mission.”

After Jack expresses interest in magic that can change the length of rose thorns, Riddle volunteers to tutor him and, when he is caught by firelotuses during Glorious Masquerade, he orders Epel to escape and save himself.

During the Lantern event he declares, “Our inability to leave the library also means others can’t use it. We positively must solve this problem.”

It seems that teachers will also receive assistance from Riddle, with Jade explaining his absence in Book 7.5 by saying, “Riddle has stepped out of class to assist Professor Trein.”

Riddle says, “In the year since I became housewarden, not a single student from Heartslabyul House has dropped out or been held back a year,” and Riddle’s tutoring of his dorm’s students plays a significant role in the Lantern event: Riddle is concerned that, in his absence, his students will not be willing to put in the word required to free him from the library “without the threat of punishment hanging over their head.”

Riddle’s fears are confirmed when the students of Heartslabyul tell Trey and Cater that they are too busy with club activities, have got other things to do, and think “it’d be nice not having someone constantly breathing down (their) necks about the rules for once.”

Cater asks, “Do you seriously believe we can keep things up like they are now without Riddle?” and a student responds, “I never asked him to help with test prep or correct my reports, but it’s definitely improved my grades.” Trey says, “I hear he’s supposed to hold a study group tomorrow for the guys that flunked their tests” and Cater follows with, “It sounds to me like we need Riddle, doesn’t it?”

Ace concedes, saying, “Who else would be enough of a weirdo to put in a bunch of work for people who never even said they needed help? Let’s make those lanterns and bring our housewarden home!,” and the rest of the dorm’s students agree, ultimately making more lanterns than any other dorm.

When the Riddle of his dream disparages studying Deuce strongly disagrees, saying, “Ever since I enrolled at Night Raven College, I’ve been learning from more than just teachers. My housewarden tutors me. Thanks to our housewarden tutoring me, l’ve started slowly getting a handle on the material. Now I enjoy school, and I’ve come to believe studying is really worthwhile.”

We see an example of this in a vignette where Deuce struggles with his math homework and Riddle provides him with what seems to be his personal reference book, that he gives to Deuce to keep. Deuce brings the book with him even when out painting roses, saying, “I was just starting to have fun with math now that it makes sense to me.”

Cater says that Riddle has been a patient tutor with him as well, which we see in a vignette where Riddle volunteers to tutor Cater on a formula that he himself has yet to learn. Riddle invites the prefect to the Equestrian Club in a voice line, saying, “You’ll find that I’m a very patient teacher.”

Riddle invites Trey to a book fair to pick out “essential reading material” for Heartslabyul’s first-year students: an illustrated etiquette manual that he can “read to (their) newest hand of card soldiers, to show them what true class should look like.”

Riddle’s wish for the Starsending event is “for Heartslabyul to soundly crush the other dorms with our scores on the next exams” (“It’s the least a housewarden can do”), but rather than rely on a wish alone he also devises a plan to help them improve. Riddle explains, “I’ll round up the students bringing down our average and hold a study group. The catch is they won’t be allowed outside the dorm until they can ace my specially-made quiz.”

Riddle says that he is particularly good at crossword puzzles and has been considering holding a speed crossword tournament to raise the grades of Heartsabyul’s students. Having created over 3,000 of his own crossword puzzles since he was a child, Riddle explains, “You need both knowledge and inspiration to solve crossword puzzles—qualities that also happen to serve you well in academic pursuits. Many students at our dorm could use more of that. So I’m sure my crossword collection will be of great use to them.”

During the Eternity Float event Riddle purchases soap as a souvenir for the students of Heartslabyul. During the Firelit Sky event Cater buys “Peacock green beaded bracelets, handkerchiefs with traditional patterns” and “individually wrapped chocolate-covered dates and little bags of coffee” for the dorm, explaining, “If I know Riddle—which I totally do—he’d refuse any gift I got him if I didn’t have something for the rest of the dorm.”

Trey says that that is why he purchased ingredients for a tart that can be shared with everyone and Jamil responds, “You’ve covered all your bases. I guess that’s why you’re the tyrant’s—| mean, your rigorous housewarden’s right-hand men.”

After Lilia makes a fruit-based version of a shaved ice for Riddle, Riddle reflects, “Food tastes better when you have it with someone else, does it…?,” and asks Lilia to show him how to make it so that he might serve it to “the Heartslabyul students who are surely carrying out their duties on (his) behalf in (his) absence.”

When Malleus says he is impressed by Heartslbyul during Halloween, telling Riddle, “You do a fine job of keeping your students in line,” Riddle responds, “I-I’m not constantly cracking a whip or anything, okay? Our students simply remain unified and carry out their duties at all times, like the card soldiers of yore.”

Riddle also expresses pride in his card soldiers during the Lantern event and his platinum birthday vignette.

Riddle seems strict about protecting Heartslabyul’s reputation, telling his students that they “have a reputation to uphold” as Heartslabyul students, that Ace performing well in his club will contribute toward Heartslabyul’s reputation, and that—during the Starsending Event—he expects Trey to do his part to “avoid bringing embarrassment to the Heartslabyul name.”

Riddle serves as the Management Committee Chairman for the VDC event and volunteers to be the only second-year student leader during Book 6 on the basis of having been Housewarden the second-longest, after Leona. Despite Azul’s pleas that he slow down his descent into Tartarus Riddle refuses, as, “I’m the leader of our team. It makes sense that I should march at the fore.”

When Azul cautions him on the fine line between bravery and recklessness Riddle responds, “There’s also a fine line between caution and cowardice…Stay sharp and follow my lead. Is that clear?”

Towards the end of their descent, however, Riddle is forced to rely upon Azul when they must navigate a space too dark for him to see, and says, “It feels strange following behind someone else.” Azul asks if Riddle is uneasy letting him take the lead and Riddle responds, “I’ll admit I’m anxious, but that’s because I can’t see in here. I have to be dependent on you.”

After Idia’s overblot Riddle orders Vil and Leona to save STYX staff members, volunteering himself and Azul to stay behind and stall the Shroud siblings. Azul is not pleased (“Did you seriously volunteer us for the most dangerous assignment without even discussing compensation?”), but Riddle says, “You can fuss all you want, but you know as well as I that this is the best plan.”

After speaking with Riddle during the Ghost Marriage event Malleus says, “I’ve witnessed firsthand how you care for your vassals and your determination as a leader. I assume you’ve received no royal tutelage, yet you have the bearing of a king all the same.”

When Riddle takes on his overblot form to battle against Malleus in Book 7 Deuce says, “My body’s instinctively tensing up just from remembering that fight,” but Ace assures him, “Now he’s fighting with us, not against us. And he’s our leader.”

Riddle declares, “I shall stand at the fore of my soldiers, just as the Queen of Hearts did when banishing criminals from her land!…I shall honor the card soldiers who fought bravely to ensure I could battle Malleus at my full strength by delivering a perfect victory. Now, follow my lead!”

After returning to the real world Riddle orders all students, not only those of Heartslabyul, to evacuate immediately if they are not a part of the core group doing battle with Malleus, and he is instantly obeyed.

When it is clear they will not win the battle against a transformed Malleus Riddle offers to overblot, but Crowley refuses to allow it (“If you do that and cause even more damage, I’ll…I’ll break down in tears!”)

Lilia is made the leader of Riddle’s group for Port Fest, saying that he would have put himself forward for consideration if he had been a third-year student.

Riddle says he always strives “to set a good example for the entire student body,” and tells Silver that, as second-year students, they cannot fail the first-year students.

During the Ghost Marriage event Malleus tells Riddle, “I’ve witnessed firsthand how you care for your vassals and your determination as a leader. I assume you’ve received no royal tutelage, yet you have the bearing of a king all the same.”

Later in the event Riddle volunteers to hold back ghosts on his own while others evacuate so that no one gets hurt.

At the start of the first Tsumsted event Riddle declares that he will be going to Heartslabyul to check on the students, ordering Cater to look into the situation and keep him informed.

When summoned by Idia at the start of the final battle against Malleus Riddle declares, “Heartslabyul shall not be defeated under my leadership! I trust you understand this.”

Upon arriving in the Spectral Realm Riddle takes immediate leadership over his group, detailing their objective and presenting a plan on how to achieve it. After they add Jade he continues to serve as leader, updating their methodology, giving orders on fight formations and giving instructions for their search, and is immediately obeyed.

Cater says that he will never forget the day that Riddle used his unique magic on Trey for the first time. Leona says, “Riddle probably just put aside his emotions temporarily, to be a proper leader,” and Cater agrees, saying, “I don’t really blame Riddle for it. He was just treating everyone equally. And I’m sure Trey knew that-which is why he supported the housewarden as much as he could even during his tyrant era. But there’s no way it didn’t wear on him mentally, IMO.”

In Riddle’s dream Ace tells Riddle about his real-world self, saying, “He’s absurdly strict on both himself and others. He stays at the top of his class in both magic and academics. He’s way ahead of even the people in other dorms. Isn’t that cool? A leader needs to be strong. mean, who would bother to obey a queen that was kind all the time?”

After falling into the abyss Riddle is met with an overblotted version of himself, demanding who ruined his rose and threatening them all with beheadings. Riddle observes, “Is that…me? My word. I don’t come off as very intelligent or sensible.”

His overblotted self responds, “Take that back this instant! I am always more calm, exceptional, and normal than any other! So why…? Why is it no one will follow me?,” and Riddle explains, “You never make the slightest effort to listen to the people around you. That’s the problem with you-no, with me. That’s why I went down the wrong path and became a self-righteous tyrant.”

After defeating the darkness-version of himself Riddle declares, “I will continue to run as fast as l am able. To be the strongest and most correct—someone worthy of having everyone bow before mel”