When Crowley asks why the students “all look so positively unenthused” about his suggestion that they all work together to take back their stolen magestone from the fairies of Fairy Gala Riddle responds, “You’re right that being unable to hold classes is a serious problem.
But is it one that students have any business addressing?,” only agreeing to assist after Crowley declares that the entire student body will be held back (Riddle: “This still doesn’t sit well with me, but I suppose we have no choice”).
Riddle is also less than enthused about going to Idia’s aid at the start of the Ghost Marriage event and, when Crowley and Ortho threaten to inform the press, Riddle responds, “I suspect the headmage would be held responsible if a scandal broke out. He’d have the most to lose.”
Later, Riddle is surprised when Rook recites a poem about Crowley, saying, “Of course it’s important to show respect to the headmage, but still…”
At the conclusion of the Tsumsted event Crowley declares, “Our journey together ends here… Let’s make it a parting to remember!,” and Riddle and Leona look equally unamused.
When Crowley announces that Malleus will be returning to NRC at the conclusion of Book 7, and, “You’ll have the opportunity to give your school chum a fresh start and continue learning alongside him. What more wonderful incentive could there be?! Don’t you feel warm feelings of hope and fraternal solidarity welling up in your heart?!,” Riddle responds, “All I feel welling up is suspicion and concern.”
When Crowley responds to the news that Riddle, Kalim, Jack and Deuce are trapped in the school library Riddle does not seem approve of his lack of urgency, saying, “Spoken with such nonchalance… But if you believe this has to do with our luck, that implies this is some sort of accident. And if an accident arises due to issues with school facilities or management, that makes it the school’s responsibility!” (Crowley: “Don’t use scary words like ‘accident’ or ‘responsibility’!”)
When Grim offers to burn the door down Crowley says, “Don’t be absurd! That door is highly valuable!,” and Riddle asks, “Headmage, did you just show more concern for the door than for your own students? That’s hardly an appropriate attitude for an educator—“
Later, Riddle agrees with Crowley that the library is “the brains of Night Raven College. It houses a great many valuable books. Forever losing access to them would be a loss for the whole world!”
Jack follows with, “(Crowley would) be like, ‘You can issue books through the window, yes?’ He’d send us back in and make us work the checkout desk forever.”
(Riddle: “It’s difficult to rule out entirely, and that’s the trouble…”)
Twisted Wonderland Reference Note 