Riddle and Heartslabyul

Riddle orders Ace and Deuce early on to “always respond, ‘Yes, Housewarden!’” 

He repeats this in his dream of Book 7 and there are many instances of Heartslabyul students responding to him with “Yes, Housewarden!” throughout the game.

It seems that as early as the opening ceremony new students found Riddle to be “terrifying,” and Book 1 begins with students of Heartslabyul struggling under the weight of Riddle’s strict rule enforcement, with one even going to Trey and Cater to say that he wants to transfer to another dorm. 

When Ace gives his fellow students a chance to stand up for themselves during the Unbirthday Party of Book 1, however, they claim to trust in Riddle’s judgement, and no students seem to have any faith in Ace and Deuce’s ability to win their duel against him, even cheering for Riddle (Deuce: “Cowards”).

After Ace punches Riddle in the face, however, the other students rise up to join him, throwing an egg at him in protest.

After Riddle nearly kills Ace via enchanted rosebush attack one student exclaims, “He’s like some kinda monster!,” in a statement that possibly resonated with Riddle: his overblotted form of the abyss in Book 7 declares, “They all look at me like I’m some kind of monster!”

The Heartslabyul students’ opinions of his conduct possibly mean more to Riddle than he is willing to let on: when memories of the revolt in Book 1 threaten to awaken him from his dream, a Cater made of darkness says, “As long as you stay here, we’ll all be on your side. But if you go back to reality, you’ll be all alone and hated again.” Riddle responds, “No… Not that… Rgh!”

Post Book 1 there seems to be lingering resentment in the dorm, with upperclassmen complaining that all Riddle know how to do is “throw senseless rules around and make his dormmates’ lives miserable,”and saying that he is “barely even fit to lead,” as well as being “small-time compared to all the other housewardens.”

In a vignette three older students release hedgehogs and flamingos onto the school grounds in attempts to get an Unbirthday Party called off, saying, “I wanted to see the tears in Rosehearts’ eyes when that happened.”

In a vignette Riddle shares that he was a victim of hazing in his first year, with upperclassmen in the Equestrian Club assigning him a horse who refused any rider except a club leader that had left three years prior.

Riddle explains, “They were hoping I’d cry about how hard that horse was to handle and withdraw from the club,” and when Rook asks what it was that brought on such behavior Riddle says, “From what I hear, it was me chiding an upperclassman every time he skipped practice or stable cleaning duty. That hardly seems worthy of a grudge, considering what | said was entirely appropriate.”

After hearing about Riddle’s poor reaction to Ace’s plans to skip school for Playfulland a group of students decide to “be careful and avoid doing anything that could cost us our heads,” while Ace reflects, “I bet a lot of these guys would easily turn me in to spare themselves the housewarden’s wrath.”

Riddle says “Students of Heartslabyul must strictly adhere to living in accordance with our rules.”

It is the Housewarden of Heartslabyul who decides when Unbirthday Parties are to be held, and Ace says, “in Heartslabyul, you have to use magic for everything when you’re recoloring the roses and setting tables and stuff,” but it is maybe unclear if it is an official dorm rule.

Riddle says that the dorm has plenty of detergent on hand “to deal with the aftermath of rose painting.”

Cater says that “It’s usually a straight shot from the mirror to the dorm entrance” when one is going to Heartslabyul, but the roses in the dorm garden are enchanted and “can be rearranged into different layouts as needed,” which we see happen in Book 7. Cater follows with, “Most students in our dorm have the layouts memorized.” It seems there is a caterpillar bigger than the students themselves in the rose maze.

When Silver asks if it is not possibly to fly over the maze with brooms, Cater throws a stick that gets snared mid-air by vines. Cater explains, “this is how the dorm keeps out intruders during emergencies.”

The roses of Heartslabyul can physically shift around on the house warden’s orders, and in Book 7 the maze goes into what Ace calls “the hither-and-thither penalty layout,” explaining, “it’s not like normal roses stay in bloom all year round, do they?”, and,

“‘Those who anger the queen in court must run through a maze with card soldiers in pursuit.’ Though generally speaking, they don’t mobilize the whole Heartslabyul student body for rule 63. Aside from that, it’s used for keeping outside visitors from entering the dorm when the school’s open to the public for events. And it’s also used for locking down the dorm building when there’s trouble.”

Ortho compares the rose maze to “a mystery dungeon with randomly generated maps,” and Trey explains that they are not holograms, but real plants that can physically change locations: “All of the flora in the Heartslabyul garden are painstakingly cultivated magical plants. They’ll even walk if they’re ordered to… Though some of them can be pretty testy and stubborn about moving.”

Trey also says that there is a Heartslabyul tradition of garden flowers holding a concert in the spring, to which he invites Ortho.

Trey explains that the flowers and trees of the garden were not planted by the current students of the dorm, but they were inherited from “generations upon generations of previous students that raised them with care.”

Trey says, “Some people get pretty mad when the roses wilt or get turned strange colors. The first thing (Riddle) did after becoming housewarden was to thoroughly fix up the rose maze.”

In Book 7.5 Trey recommends that Ace ask Riddle to order the roses to make some space in the garden for him to practice his unique magic.