Riddle and Cater


After Trey is injured in Book 2 Riddle tasks Cater with looking into the circumstances behind the rise in injured spelldrive athletes, and Cater is entrusted with a significant role in Riddle’s plan to catch Ruggie and Leona. 

When the campus is visited by tsums during the Tsumsted event has Cater invstigate the situation while he goes to check on the dorm. Riddle later thanks Cater for his assistance ensuring that he had been able to keep the students updated, and Riddle receiving information from Cater is a common theme: he says he has heard about how to play bobbing for apples in the Shaftlands from Cater, Cater once told him about a time he failed to take a picture of Malleus, and Cater has also told him New Year’s mystery bags.

When Riddle finds himself without any clothing casual enough to be appropriate for a visit to town with members of his club he goes to Cater and Ace for advice, also going shopping with them so that they could help him with “picking out a few clothing items.”

When Cater is surprised by the dream-Riddle of Ace’s dream dressed in beachwear the dream-Riddle immediately goes to Cater for assurance (“…Does it look strange?”), so Ace’s idea of Riddle might involve him going to Cater for help with fashion.

At the start of Beanfest Cater warns Deuce to be wary of Trey as “It’s the guys who act all harmless that you really gotta watch out for,” and Riddle agrees with him, only to later be caught by Trey himself: “Cater was right all along. It’s the ones who act harmless that you truly have to watch out for.”

After attempting to surf for the first time during the Stitch event, Riddle says, I should invite the rest of Heartslabyul to the beach once we return. I bet Cater and Deuce would especially enjoy it.”

Riddle says the he would cut his hair himself when he first got to NRC in order to keep it short, but “Cater didn’t want (him) doing it for some reason…” (Jamil: “You should probably thank Cater for that.”)

During Halloween Riddle says, “I’m satisfied that our costumes are both refined and fearsome—a perfect fit for a dorm embodying the spirit of strictness.,” praising “Cater’s skills and know-how” for making it all possible.

While setting up for an Unbirthday Party members of Cater’s group become frustrated at how he is constantly updating Magicam and they complain to Riddle, expecting to see Cater punished. Cater greets Riddle by taking another photo (Heartslabyul Student: “The audacity of this guy…!”), but Riddle only reminds him about the importance of proper aesthetics in tea parties.

The members of Cater’s group are displeased, saying, “Did the housewarden just…completely ignore an upperclassman slacking off? No ‘Off With His Head’ or anything?,” and, “Turns out you can do whatever, so long as you’re one of Housewarden Riddle’s cronies.”

When the group members lose track of instructions for putting the teaware away after the party Riddle becomes enraged and the student all blame Cater, saying, “Cater was the one in charge, and he was goofing off the whole time we were setting up,” and, “Where’s your sense of leadership, Cater?”

Cater immediately apologizes, but when he posts to Magicam again the Heartslabyul students tell Riddle to punish him (“‘Off With Your Head’ him already!”).

Looking at Cater’s Magicam, Ace realizes that they can the hashtags on his photos can be used as a reference guide to put the teaware away properly even without the instructions. Cater’s group members are not pleased (“That guy’s got all the dumb luck”), but Trey and Riddle suspect it was not luck at all, with Riddle saying, “He was using this little ‘mishap’ as a way to enlist help from outside his group.”

When Cater apologizes for getting dirt onto people during his Halloween performance Riddle is unconcerned, praising him for acting talent. When Ace complains about being “all dirty and grimy” it is Riddle who responds, “We knew that would happen going in. You can’t win a battle without accepting a few sacrifices.”

After hearing about Cater’s experience during the Diner event Riddle says that, as Housewarden of Heartslabyul, he is quite proud of him.

Cater greets Riddle as “lookin’ adorbs, as always” at the start of Book 1, and when Riddle agrees to overlook mistakenly unpainted roses at the end Cater responds, “That’s so generous of you!”

When Riddle claims that he has become “much more lenient about enforcing the rules” Cater agrees, saying, “He’s way nicer than before. And we all appreciate that Riddle diligence,” and he also praises Riddle for cutting off Leona’s magic in Book 2.

When Grim comments on how the Heartslabyul of Cater’s dream is “way too different from regular Heartslabyul. But everyone seems like they’re havin’ more fun this way…” Leona says that they might just wish it was reality, and Deuce wonders Cater has “some issue” with Riddle.

Leona responds, “How could he not? How would you feel if a guy who enrolled after you brought you in line and bossed you around through sheer magical chops?”

When Deuce says that the older students have never mentioned how Heartslabyul was before Riddle took over as Housewarden Leona says, “Doubt it’s a topic of conversation they’re eager to bring up. The current juniors were freshmen back in those days. They had to respect the pecking order whether they liked it or not. So imagine how it must feel for some fresh-faced kid who enrolled after you to march in, behead the previous housewarden, and change everything.” (Idia: “Not much they could do but say ‘Ah, welp, this is my life now…’”)

Leona suggests that Trey and Cater might have been planning to use Riddle: “You know, propping up a young and impressionable king, overthrowing the old order, and starting a revolution. Then installing yourselves as regents or advisors and manipulating the king to build the kind of country you want. Happens all the time, right?”

Deuce argues that “Cater and Trey would never do that!,” but then follows with, “They might say mean things sometimes, but they’re caring and sincere! At least…l think they are…”

Idia follows with, “Cater and Trey are juniors at Night Raven College, AND they survived Heartslabyul at its very worst. They’ve gotta be clever and calculating,” and Leona adds, “You can never tell what they’re thinkin’ under those smiles. Personally, I’d never pick those guys for adjutants in a million years.”

Afterwards Deuce tells everything to Cater himself, but Cater insists, “I’m not unhappy with the Heartslabyul we’ve got. I mean, I wouldn’t say I’m TOTALLY happy with it, but I’m not the least bit interested in unseating Riddle and taking his housewarden spot. And even if I DID challenge him, I’d be like 99 percent likely to lose,” telling Idia and Leona not to give the first-year students strange ideas.

Leona says, “I’m not hearin’ a word of denial,” and Cater responds, “I’ll deny it right now! Cay-Cay and Trey are cool, caring, dependable upperclassmen.”

Later on Cater quietly reflects, “Being a housewarden SO isn’t my style. Why’d I ever even have this dream?,” and Silver assures him, “Oftentimes in Malleus’s dreams, you get what you want, but it’s distorted in some way. I’d say there’s no need to read too much into it…but it’s probably hard not to dwell on it, huh.”

Cater says he is already over it, but follows with, “…Just don’t tell Riddle, okay?”

In Book 7.5 Jamil and Azul also reflect on the curious nature of Malleus’ dream worlds: “Our dreams were exaggerated and distorted in weird ways, but they were still our wishes, in part.”

After they reach Trey’s dream Leona observes, “both of Riddle’s adjutants had dreams where he’s been replaced as the boss. I’m startin’ to feel bad for the guy.”

Idia follows with, “The scariest type of person is someone like Trey or Cater who’s all smiles and never shows what they’re thinking,” but Ortho reminds them, “If something’s different from reality, that doesn’t necessarily equate to the dreamer being unhappy with the status quo.”

Cater admits,

“I’ve definitely fantasized about spending every day at school partying it up like it was my birthday…but it’s not like I ever went so far as to consciously wish to be housewarden…But seeing the kind of peaceful world Trey wanted is making me think. I’ve stayed comfortably on the sidelines ever since | started school here. That’s where I set up camp back when the dorm was wild and chaotic, and I didn’t budge an inch after Riddle enrolled. Doing otherwise seemed like a hassle… Not to mention scary. I figured all I had to do was coast along, and I’d be outta there in three years. But in hindsight… I’m sure there were tons of ways I could’ve contributed.”

Leona argues otherwise, telling Cater, “Don’t flatter yourself.”

Trey identifies a dream-Cater masquerading as the real-Cater in Riddle’s dream by claiming that Cater once got a form for challenging Riddle to a duel toward the end of their second year.”

Trey reflects,

“What was it again? If you can’t imagine something, then you can’t manifest it in a dream? I guess since Riddle got his spot by overthrowing the last housewarden, it makes sense he’d expect some challenges himself. But even if Cater DID want to be housewarden, he’d never share that with anyone else. And he certainly wouldn’t be dumb enough to bring a duel challenge form into a place where Riddle has a chance of seeing it. That’s precisely why I trust him. He’s always walking on eggshells to avoid angering our queen. Though, I suppose the darkness wouldn’t understand anything about that.”

In Cater’s dream of Book 7 dream-Riddle is in charge of beheading those whom Cater orders him to, and seems strict about staying on schedule so that Cater will be on time for Magicam livestreams. Later in the dream, dream-Riddle DJs a party.

When the Chenya of Riddle’s dream encourages the group to let Riddle stay asleep Cater refuses, saying, “If someone’s gonna be in charge of the card soldiers…it’s gotta be the strongest, prickliest queen there is!”

While it is difficult to tell due to the limitations of the visual novel medium, after Riddle awakens from his dream Cater seems to hug him (Riddle: “Cater… Little less tight, please…”).

When Riddle wonders how they are to confront both Malleus and Lilia at the end of Spectral Soiree it is Cater who assures him that the group of recently-possessed student will be joining the fight, and Cater who tries to get Cater and Deuce to respond “Yes, Housewarden” to Riddle in Book 1, shortly before they are removed from the dorm. 

When Cater is less than thrilled about fighting an overblotting Leona in Book 2 Riddle tells him that he is free to run if he is afraid, but Cater insists on staying (“We do this together, Housewarden!”).

Cater says “Trey wouldn’t let me hear the end of that” in response, and this exchange is also touched upon in the novel: 

“Cater has just said that he and Yuuya are always getting into these situations, but Yuuya knows it isn’t true. Unlike Yuuya himself, who has no magical power, Cater should have been able to evacuate on his own without too much difficulty. But he won’t run. Just like the mock Spelldrive game against Savanaclaw, just like Riddle’s overblot—he stayed.
In the end, Cater looks out for those around him. That’s what Yuuya thinks as he watches Cater, glistening with sweat. He jokes that he fears Trey’s rage, but there is no regret on his smiling face. 
‘I’m here with you until the end, Housewarden.’
‘Very well. That is what it means to be a Heartslabyul student, after all.'”
-Twisted Wonderland the Second Novel (fan translation)

When Cater disappears at the start of Spectral Soiree Riddle says, “Though I chide him for talking too much, I admit it’s strange to not hear his quips right now,” and we see Riddle scold Cater in a vignette where he uses his unique magic to try and get out of running laps. Cater tries to flatter his way out of getting into trouble (“You’re so cute that you could almost pass for a butterfly!”) and Trey warns him to give up (“You really think you can con Riddle, of all people, with a bunch of random compliments?”), with Riddle saying that he will be reporting Cater’s conduct to Vargas, saying, “Had it been a DORM rule, it would have been ‘off with your head’ right away.”

We also see Cater flatter Riddle in other vignettes by commenting on how cute he is.

When Jamil asks Riddle to help him and Kalim practice flight as “the perfect teacher,” Riddle responds, “I see you share Cater’s total lack of reluctance to pester me for favors.”

During the Eternity Float event Riddle purchases a comb designed to look like a fork as a gift for Cater, saying, “Cater would love getting something that’s limited-edition.”

In a vignette Riddle volunteers to tutor Cater on a spell formula that he himself has not actually learned yet as he is a year behind Cater in school, going to the library and collecting together what Deuce describes as “at least twenty grimoires” to create a 300-page guide for Cater.

When Cater fails to memorize it Riddle is unamused, with Trey telling Cater, “Put some effort into your memorization. Our housewarden took a lot of time out of his busy schedule to make this for you.”

After Cater leaves, however, Trey gives Riddle advice by asking him how he would go about eating a plate of food that he disliked. Riddle comes up with the solution of eating “dispreferred food alongside something | DO enjoy eating…” and has Trey teach him how to make a Magicam account, which he uses to tutor Cater through hashtags. 

Cater is able to pass both the written and applied portions of his exam, and thanks Riddle for his help (Riddle: “After the thorough job I did of tutoring you, that’s the least I would expect”).

Cater says he has made a reservation at a pancake cafe as his way of saying thanks, but Riddle presents him with a pile of books, saying, “This is just the beginning. You’re going to read all of them to prepare for your next test!”

We see Cater apply what is possibly the same spell that Riddle taught him in another vignette to clean up after a party.

Trey says, “And here Cater struggled with practical magic until just recently,” and Riddle observes, “His talent really shines when getting through something efficiently serves his own interests. It’s quite calculating, really.”

When Ace goes to Vil for advice on how to calm an angry Riddle Vil responds, “Own up and apologize!…The best way to earn Riddle’s forgiveness is to accept his anger head-on,” and Cater is quick to apologize to an unhappy Riddle during the Starsending event and in Book 1.

Also in Book 1 Cater encourages Ace to apologize to Riddle, and when members of Heartslabyul accuse him of being a poor leader (in front of Riddle), he immediately apologizes.

Cater identifies a dream-Trey masquerading as the real-Trey in Riddle’s dream by pretending that he and Trey once considered transferring to Scarabia to escape Riddle.

Cater says,

“It’s true things grew pretty strained in Heartslabyul, and Riddle’s tyranny was a scary sight to behold. But honestly? Unlike the rest of you guys, l’ve never once been beheaded by Riddle in these past two years. I had things under control. Frankly, I’m pretty sure I could’ve made it to graduation with a perfect zero-beheading record. I’m finally in a place where I don’t have to constantly move to suit someone else’s convenience. Why would I CHOOSE to move?”

It is possible that Cater still has yet to ever be collared by Riddle’s unique magic.

Cater follows with, “This faker easily played along with that whole story about transferring dorms.  That means Riddle wouldn’t put it past us-the way he perceives us. Riddle really doesn’t get it. Followers have their pride too, y’know?”

The darkness-Trey responds, “…What a shame, Cater. I hope you know I always thought someone like you was worth a baker’s dozen of his peers,” but it is a little unclear if this was meant to represent Riddle’s thoughts speaking through Trey-shaped darkness.

When Riddle tries to use his unique magic on Ruggie on Book 2 without his magical pen Cater holds him back due to how he has only recently recovered from his overblot, and when Riddle seems to come close to using his unique magic on campus visitors during Halloween Cater tells Deuce, “Let’s protect those visitors from Riddle, for Riddle’s own sake.”

Riddle tries to keep Riddle from becoming too enraged at the first-year students in Book 1 by reminding him that Ace’s group is still new to NRC, and directly before Ace and Deuce’s duel for Housewarden Cater tries to intervene by pointing out how he might be late for his afternoon tea. 

After Riddle becomes angry at Floyd at the beginning of Book 4 Cater tries to hold him back, and when Riddle becomes enraged at Deuce in the battles leading up to Malleus in Book 7 Cater reassures him that Deuce has learned his lesson. Riddle responds, “I suppose. In hindsight, it was a winning play. I’ll defer to you and let it slide this time, Cater.”

Watching the battle Floyd observes that Cater is “pretty good. He’s decent in a fight, and he can even soothe the raging Goldfishie.”