Riddle and Chenya

We see Riddle meet Chenya for the first time in a flashback from when Riddle was possibly around eight years old, with Chenya and Trey knocking on a window of Riddle’s house and inviting him out to play.

When Riddle refuses because he is doing independent study Chenya replies, “‘Independent study’ means you pick what to do, right? My grandpa says play is a form of study!”

Later Riddle reflects, “I had the best time playing with Trey and Chenya. We did so many things I’d never done before. They taught me lots of things I didn’t know,” and says that he would sneak out of his room every day to play with them, which we later learn lasted for one or two months.

According to Cater, Chenya “sometimes pops by (their) dorm to visit,” and Chenya appears for the first time in the Main Story in Book 1, saying that Riddle has “always been quite strict” and recommending that Ace’s group confer with Trey if they want to know more about “what created such a control freak.”

Trey is surprised when Ace reveals that he knows that he and Riddle have known each other since they were children, but when Deuce says they heard from Chenya he does not seem surprised, saying, “That explains it.”

Chenya invites himself to the Unbirthday Party at the end of Book 1 and it is revealed that he is a Royal Sword Academy student. He appears again in Book 5, commenting that they haven’t seen one another since Book 1 as Riddle had been unable to meet during Winter Break.

Riddle tells Chenya not to use his unique magic to surprise visitors to the school and Chenya replies, “No promises. Maybe if I’m feeling charitable!”

Chenya appears again briefly at the end of Book 5, cheering for Neige’s group during the VDC.

In a vignette Riddle explains that crossword puzzles were the only form of entertainment he had been allowed as a child and, at one point, he started making his own crosswords to give to Trey and Chenya one day, but it is possible that he never had the opportunity to do so. He says that, over the years, he has created over 3,000.

Riddle has an NBC voice line of, “If Chenya were here, he’d fit right in with the rest of the town. He’s as much of a mischief-maker as the locals.”

Chenya is a part of the Royal Sword Academy group that attends the school social of the Glorious Masquerade event (Riddle: “I see Chenya as well. I wasn’t expecting to run into him here”), and joins the NRC students in sending up magical fireworks during the festival.

After Rollo’s firelotuses are unleashed that night Chenya sacrifices himself to protect Riddle and Deuce (“Riddle, stick behind me. You too, card soldier!”). Riddle argues, “I never asked you to cover me! I can fight!,” but Chenya tells them to leave while he distracts them before getting overrun and collapsing.

Chenya appears at the end of the event seemingly having made a full recovery. Riddle scolds him for scaring people with his unique magic and Chenya responds, “Hey, I make my entrances how I want.”

Chenya seems to also join the festival during Port Fest: Trey explains that he left their booth to talk with an unnamed person from his and Riddle’s childhood and, in Trey’s absence, Lilia crafted his own version of the clam chowder they were selling, which the visitor then ate (Jack: “Oof, I’m sorry”).

In Trey’s (and Riddle’s) dream of Book 7 Chenya appears without a “?” by his name, which we learn in Leona’s dream seems to denote when a character is a creation of the dreamer’s mind rather than being made of darkness: 

Ruggie: “Maybe he wasn’t darkness, just a regular NPC?”
Ortho: “Maybe in these dreams, accurately representing the dreamer’s perceptions-or wishes-takes priority.”

The Chenya of Trey’s dream is Housewarden of Heartslabyul. Trey explains that Riddle challenged Chenya for the position soon after enrolling, but, as Chenya explains, he is impervious to Riddle’s unique magic.

Chenya says that spells pass through him, leaving Riddle perplexed during their duel for Housewarden, “and before he could get his bearings, I hoisted him upside-down by the belt of his pants. I asked him, ‘So, can you stand on your head?’ Then his pants came loose in spectacular fashion.He got so mad, he turned red as a tomato…Heheheheh!”

Trey says that, while Chenya had been able to avoid Riddle’s unique magic, Riddle still could have attacked him with other spells. Chenya says, “But he didn’t, did he?,” and Trey responds, “Only because it was you he was facing. He would’ve left anyone else charred on the ground in seconds.”

Leona observes that, in Trey’s dream, he has “a version of Riddle who pulls his punches against his childhood friend.”

In Riddle’s dream Chenya is a bassist in Riddle’s two-person band, meeting with the group after a surprise live-performance in front of a station. Chenya says that Riddle will “jump between punk, hard rock, pop, and rap. Of course not everyone can keep up.”

The family photos on the walls Riddle’s living room include both Trey and Chenya, taken during school events, holidays and vacations that their families all took together.

Trey reveals, however, that the events in the photos were all fabricated by Riddle: “We only played together for one or two months, tops. Riddle always went to a private school, and Chenya and I went to public school. We’ve never all gone to the same school before. So we’ve never competed in the same field day. And we’ve never vacationed together.”

While Riddle himself is magicless in his dream, Chenya is still a mage (Riddle: “But he never shows me anything when I ask”).

After the group becomes trapped in Riddle home as it fills with tea and tears and Trey asks Chenya to take them to Riddle, who says, “Just let him sleep. He’s so much happier and having way more fun here in the dream. He’s got a nice mom and dad. And no magic means no need for a bunch of mind-numbing academics. If he wakes up, all the memories of his family and friends on these walls will go poof. Would you wake him up regardless?”

Ultimately Chenya does guide the group into a deeper level of Riddle’s dream, where Riddle is “in full-on teapot tyrant mode, terrorizing the dorm into obeying him.” Chenya says, “I could always make it worse,” flipping Riddle over in a manner similar to which he described happening during their duel for Housewarden.