Riddle and Jack

In an early interaction where Riddle threatens to behead the first-year students for fighting on campus Jack tells Ace, “I thought he looked like a wuss, but your housewarden is one scary dude.”

Jack targets Riddle during Beanfest, but Riddle is protected by Deuce.

When happening upon Jack in the Heartslabyul lounge in a vignette Riddle observes, “To think we have a guest and no one has deigned to offer him tea. What an affront to our storied tradition of hospitality.”

Riddle offers to prepare tea for Jack himself. Jack refuses (“I couldn’t have the housewarden of Heartslabyul make tea for me!”) and says he will make the tea on his own, but Riddle responds, “There is no need to be so humble. You don’t even know where we keep our tea leaves.”

Ace is amused by seeing Jack in Heartslabyul’s lounge, saying, “It’d be weird enough seeing him sitting in our lounge, but with (Riddle) standing next to him, it’s so much more…Aha ha!”

Jack says that he is aware, but Riddle responds, “1, for one, see nothing amiss here. All that is required of Heartslabyul’s students is the same stringency the Queen of Hearts herself possessed.” (Jack: “Uh, th-thanks…”)

After Ace incorrectly guesses that Jack is from Sunset Savanna based on the assumption that everyone from the Shaftlands, Jack’s country of origin, was “all flashy and dapper and stuff,” Riddle cautions him, saying, “You are making yourself sound quite narrow-minded, Ace. A person’s hometown or upbringing has no bearing on their character. All that matters is what they are capable of.”

Riddle compliments Jack on his ability to notice Ace cheating at a game of cards and Ace asks, “Wait, Jack, is your tail wagging?” (Jack: “No.” – Ace: “It’s wagging so hard that it’s sending the cards flying!”)

Jack says, “I really…r-respect…Riddle,” complimenting him on ranking first in written exams, being a talented mage, the effort he puts in, and comparing him favorable to Leona.

Jack explains that he has looked up to Riddle ever since he saw him practicing a spell to change the length of rose thorns (Riddle: “If I can get it right, then it will save both the plants and their caretakers a lot of pain during the pruning process”), as he has practiced the same thing with cacti. Riddle responds, “If you’re that interested in the art, then allow me to teach it to you sometime. I’ll have you know I’m a strict teacher, though. Fair warning,” and Jack is delighted (“That’d be like a dream come true. Can’t wait, man! Er, sir!”)

Ace comments, “Never in a million years would I have dreamed these two’d hit it off. Talk about an odd couple.”

Riddle compares Jack favorable to Ace (“You are a diligent and upright young man…unlike some of our first-years”), and assigns Ace the task of laundering the ceremonial robes of everyone in the dorm in punishment for cheating at cards. Jack volunteers to watch over Ace and make sure he doesn’t sneak off and Riddle replies, “I like the way you think.” (Ace: “I never should’ve brought these two together.”)

In Book 5 Riddle approaches the sports clubs who are setting up the stage for the VDC with, “Chatting on the clock? You must be quite confident in your progress setting up. I trust work is proceeding on schedule?,” and Jack greets him with, “R-Riddle, sir! Hello, sir.”

In a Lantern Event voice line Jack says, “I can respect Riddle’s work ethic and huge breadth of knowledge. I just wish he wasn’t so inflexible.” In contrast, Riddle has a voice line of, “I wish Jack wouldn’t act on his own so conspicuously. He really ought to be following my directions if he wants to get out of this mess.”

When Jack is torn between having to ask Leona for help or leave the work that needs to be done to other dorms Riddle says, “You have some irksome personal hangups.” Jack responds, “You’re not wrong, but you’re the last person I wanna hear that from…”

In a tsumsted voice line Riddle says, “I passed by Jack a short while ago. Not only did HE give me a polite nod, but so did his tsum. I did a double take at that.” 

In a birthday voice line Jack says, “Riddle-senpai’s words of encouragement really hit home. It made me way happier than someone telling me to take it easy because it’s my birthday.”

Riddle compliments Jack on his painting and observational skills during the Lantern Event (Jack: “Never thought I’d get so many compliments for just painting a picture…”) and again during Fairy Gala IF on how his efforts have improved his ability to walk in heels.