Jamil does not seem to be overly fond of Riddle: in an early vignette he refers to Riddle as “a stern and uncompromising leader,” but then follows with both Kalim and Riddle being “alike in their ability to cause ceaseless stress.”
When Cater and Trey explain how they have both gotten souvenirs during the Firelit Sky event for the students of Heartslabyul because Riddle would “refuse any gift (they) got him if (they) didn’t have something for the rest of the dorm,” Jamil responds, “I guess that’s why you’re the tyrant’s—| mean, your rigorous housewarden’s right-hand men.”
After Riddle warns Jamil and Azul about a potionology assignment Jamil says, “I must say, it’s rather…generous of you to share your insights on an exercise that you couldn’t solve yourself,” to which Riddle responds, “…You think I’m up to something,” and reveals his frustration with Crewel saying, “this year’s sophomores were a sorry bunch” when his entire class failed the project.
Jamil says, “You’re always at the top of your class. Surely if YOU failed the assignment, the cause must have been some minor missed detail, or—“ but Riddle interrupts with, “Don’t patronize me.” After Riddle leaves the scene Jamil reflects, “Riddle always takes everything so seriously.”
During the Nightmare Before Christmas event Jamil says that Azul would be “the last person (he’d) ever want to group up with,” but when the group assignments are revealed he says, “I can’t believe I landed on the same team as Azul… And worse, Riddle.” (Riddle: “How am I ‘worse?’ I’d consider myself a dependable teammate.”)
Jamil laughs when Azul and Riddle are both startled by Jack Skellington (“It’s not every day I get to see Riddle and Azul both looking so panicked”), and when Riddle abandons their group in his efforts to recite a poem to Lock and Azul then follows after Riddle so as not to allow him to do anything that will get them sued, Jamil asks Jade, “What is WRONG with those two?!”
Riddle has a voice line of, “I don’t know if it’s his posture or something else, but being dressed like that really brings out Jamil’s character…it’s a bit menacing, in a way.”
Riddle tells Kalim that he is “so lucky you have Jamil to look after (him),” and in a vignette where he gets Kalim to agree to not “say a word” after they do a sprint together Jamil thanks him for “babysitting” Kalim and Riddle responds, “Not at all. You deserve a break once in a while.”
When Kalim then immediately does the very thing he said he would not do (saying, “It’s kinda nice to see even you can’t come first in everything, Riddle”), Jamil interrupts before Kalim can any ruder, apologizing to Riddle on Kalim’s behalf.
Jamil seems aware of Riddle’s capabilities in both academics and in flight: in a vignette where he needs access to the results of week-long experiment that Kalim either did not do or does not have the results for in order to do Kalim’s homework, he accepts Riddle’s notebook from Floyd despite suspecting that it has been stolen so that he can use it for the assignment.
In another vignette Jamil suggests to Kalim that they practice their flying, as they “have the perfect teacher right here,” in reference to Riddle. Riddle responds, “I see you share Cater’s total lack of reluctance to pester me for favors” and refuses to teach them how to fly, though he does agree to allow them to watch him.
When Kalim becomes locked in the library Jamil asks who he is stuck with, and upon learning that Kalim is with Riddle, Deuce, and Jack he responds, “If Riddle’s there, it should be safe for me to step away for a bit.”
Riddle and Jamil come together during Glorious Masquerade to tease Sebek.
Twisted Wonderland Reference Note 