When asked about Malleus not attending Housewarden meetings the previous year Leona says, “You have NO IDEA how much I suffered last year,” to which Riddle responds, “You just gave the orders. I was the one doing the actual suffering.”
After describing the lengths that they went to in order to contact Malleus, Leona says, “Why should the rest of us put in a ridiculous amount of work when Malleus won’t?,” and Riddle follows with, “Again, it was I who put in the ridiculous amount of work…”
Riddle’s first attempt to collar Leona in Book 2 results in the first (and, as of this writing, the only) example of Riddle referring to an upperclassman without an honorific, calling him “Leona” instead of “Leona-san.”
Riddle’s second attempt at collaring Leona succeeds, but it is then broken off by the negative energy of Leona’s overblot.
Leona is collared a second time in Book 7 when he threatens to turn the house of darkness in Riddle’s dream to sand. When he orders Trey to overwrite it Cater says, “Can’t you break it like you did before?,” and Leona replies, “I would’ve if I could…not the kinda thing you can do reliably every time.”
When Trey is then also collared Leona says, “I had a feeling.” Trey asks, “Did you just use me to test it out?!,” and Leona responds, “You think I’d accept being the only guy wearing this dorky collar? Get outta here.”
Leona seems aware of Riddle’s strength, saying that he knew the students of Savanaclaw would be no match for him in Book 2, and when a darkness-Ace comments on Leona’s unique magic being powerful enough to block Riddle’s, Leona responds, “That was more of a fluke.”
Leona is unapologetic when the spelldrive team sends a rogue disc towards Riddle, intercepted by Ace. Ace says, “If I wasn’t with him, our housewarden would’ve been seriously injured,” but Leona responds, “Riddle woulda batted that little disc away with his magic, no problem,” confirmed by Riddle himself (“Even if what he said is true, there is such a thing as tact”).
Riddle’s team struggles to find a lanternblossom during Vargas Camp, with Sebek discovering one just as Leona’s team arrives, with Leona explaining, “These guys wouldn’t stop whining about how they can’t find a lanternblossom. They kept interrupting my nap, so I decided to find one and shut ’em up.”
After Leona’s team members spot Sebek’s lanternblossom Riddle tells them that the Equestrian Club had found it first, but they respond, “So what, you calling dibs or something? You don’t got it ’til you GOT it, man,” deciding to climbs up the cliff and take it before Riddle’s team is able to.
Leona interrupts, however, telling them “Only chumps bite at whatever bait dangles right in front of them,” but after they search the forest they are still unable to find one: it is unconfirmed but maybe possible that Leona called off his teammates just to keep them from stealing from Riddle’s group.
CHARON render Riddle unconscious during their battle at the start of Book 6 and Riddle wakes up ready to fight, but he is met with Leona asking, “Is that anyway to greet the guy who’s lap you’ve been snorin’ on for three hours?” (Riddle: “I was wondering what this muscley pillow was… I’m so sorry! I’ll get up right away!”)
While Riddle’s respect for Leona is stated plainly in the novel adaptation, different to the canon of the game, but after he collars Leona in Book 2 he does say, “I understand the irony of me being the one to say it, but it pains me to see you like this. You’d be wise to confine yourself to your room and try to calm down!,” rather than gloat or scold him.
“Riddle confronts the glowering Leona with determination. ‘I am not mocking you. Leona-senpai. I respected you.’
Cater looks at Riddle with surprise, while Ace and Deuce’s eyes go wide. None of them could have ever imagined Riddle saying such a thing, and with such honesty.
Yuuya remembers what Riddle said when they were discussing Malleus: a good housewarden. A respected housewarden. Riddle has always longed to know more.
‘I envied you, for how the students admire you. I wanted to be a housewarden beloved by everyone, like you.’ Riddle looks pained. ‘I made a mistake…so I wanted to become someone like you, Leona-senpai.’
His voice is trembling.”
– Twisted Wonerland the Second Novel (fan translation)
When Cater tells the group of Book 7 “I’ll never forget the day Trey broke the rules and Riddle Offed him for the first time,” Leona seems to defend Riddle’s decision, saying, “Riddle probably just put aside his emotions temporarily, to be a proper leader.”
When the Chenya of Riddle’s dream suggests that the group let him stay asleep, Leona responds, “All I know is, if he ditched his magic and his studies, he wouldn’t be the prickly punk he is. No matter who’s tried to prune him out, he’s kept on growing, those sharp thorns stabbing through anything in his way. You wanna let the monster that managed to collar me not once but TWICE wilt here?”
When Trey worries over Riddle being left alone in an abyss Leona says that Riddle “capable of handling whatever wild stuff may or may not get thrown his way.”
After scolding Kalim for yawning during Housewarden meetings Riddle reflects, “Considering you and Leona-senpai, maybe sons of wealthy families are ill-suited to being housewardens…?”
When Kalim suggests that Leona will be willing to help the Lantern Event group and say, “No worries. We gotta look out for each other, right?,” Jack says, “I don’t think he’d say ANY of that,” and Riddle agrees, saying, “This is Leona we’re talking about… He’s more likely to ask how we”re struggling so much with not one but TWO housewardens present.”
When Sally describes Leona as “such a well-mannered young gentleman” and Jamil says, “Are we talking about the same person?,” Riddle responds, “That’s an acerbic remark… Though I can sympathize with the sentiment.”
Riddle disapproves of Leona’s solution for Fairy Gala IF being to “dump the job” on first-year students, saying, “For him it is simple. He doesn’t have to do anything. How inconsiderate to his students.”
Leona responds by telling Riddle he sounds jealous, “All those herbivores with zero initiative, who’re totally helpless without their housewarden,” and “can’t think for themselves,” and Riddle goes from disapproving of Leona’s suggestion that they assign first-year’s to the task to volunteering Ace’s participation. Leona says, “Great. I’m feeling reassured already,” and Azul observes, “Leona just played Riddle like a fiddle.”
Leona and Riddle might agree with one another on the subject of Crowley: when Crowley’s reaction to the students being kidnapped at the start of Spectral Soiree is “HOW AM I SUPPOSED TO EXPLAIN THIS SCANDAL TO THE PUBLIC?!,” Riddle says, “THAT’S what you’re worried about?!,” and Leona follows with, “All he cares about is covering his tail,” while they both appear equally unamused at the end of the Tsumsted event.
When Leona rejects Crowley’s suggestion that they retire Malleus from the inter-dorm spelldrive tournament by saying “Ain’t nothin’ I hate more than someone tellin’ me ‘you can’t win’ before I even begin to fight,” Riddle agrees, saying, “As one of the foremost mages here, the last thing I want to do is give up without a fight.”
When Riddle awakens at the end of Book 7 Leona says, “I’m hurting all over, and I’m running on fumes magic-wise. You really made me work for this,” and Riddle responds to both Leona and Silver, “I fear you’ve seen me at my absolute worst.”
Twisted Wonderland Reference Note 