Dire Crowley/Relationships

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Ramshackle

MC

Crowley is the first person to find MC and also to learn that they've came from a different world. After learning that MC has no magical powers, he offers MC to stay at Ramshackle Dorm along with Grim "free of charge". However, as they still need to buy food and clothing, it's in exchange of MC (and Grim) doing odd jobs around the campus, thus appointing them to be the new "janitorial staff".

Later on, after MC, along with Ace, Deuce and Grim successfully retrive a magestone from the dwarfs' mine, Crowley claims they possess the talents of a beastmaster. He allows MC to become a student of NRC, and enrolls them with Grim as one student. He gives MC a ghost camera, telling them that he would like them to photograph Grim and other students and make a record of their campus life.

Though he often reassures MC that he's looking for ways to send them back, it's unknown if he's telling the truth. Crowley also leaves MC in charge of taking care of NRC related troubles or tasks, such as appointing them to find out more about why students keep getting injured in Book 2 or making them the manager of the SDC group and even assigning MC's dorm to be the ground for the training camp during the events of Book 5.

He is shown to have high expectations towards MC and Grim, even if it isn't yet explained the reason. At the same time, however, Crowley has shown a certain disinterest in their care. For example he does not inform them about Halloween, doesn't try to help them when they are chased out of their dormitory by Eliza's ghosts and might have forgotten about them completely during Spectral Soiree.

Grim

Originally, Crowley refused to let Grim stay or study at Night Raven College as he was not chosen by the Dark Mirror. He also considers Grim a monster. But after the please of both Grim and MC, he reconsiders it and allows Grim to stay - still not as a student, however.

After the events of the Prologue, Crowley acknowledges that Grim possesses sufficient talent to become a mage. He enrolls Grim and MC as a single student and gives Grim a magestone collar. To try to get him to carry out his assigned tasks, Crowley often bribes Grim with food or promises which, though false, somehow end up coming true.

He is shown to have high expectations towards him and MC, even if it isn't yet explained the reason. In Book 6 Crowley shows an unusual act of concern after his return from the Island of Woe. Grim himself is bewildered by this.

Heartslabyul

Ace Trappola and Deuce Spade

After Ace and Deuce (along with MC and Grim) caused trouble on campus, even destroying a rare magestone, Crowley tells them that they would be expelled - unless they return with a magestone by the following morning. However, when the group actually brings him a magestone, Crowley is shocked as he was not expecting them to go through with it. He's moved that his students joined forces to defeat a common foe and he revokes their pending expulsions.

When Ace gets into trouble with his housewarden, Crowley suggests that he could transfer to a different dorm. When Ace refuses the idea, Crowley says he should challenge Riddle for leadership of the dorm and that he would fill out the necessary paperwork for such a duel.

Riddle Rosehearts

Like most students, Riddle doesn't have much faith in him. In Book 1 he openly expresses his disagreement with Crowley's habit of tolerating rule-breakers.

Trey Clover

Like most of the students, Trey seems suspicious of Crowley. In reaction to being selected as a Stargazer during the Wish Upon a Star event, he is shown to be very hesitant to believe that Crowley used astrology to choose his students.

Savanaclaw

Leona Kingscholar

As is deduced several times, Leona doesn't like Crowley.

Jack Howl

Like most of his students, Jack has no faith in Crowley, as seen in some comments at various events. Crowley seems equally unimpressed with Jack, call him “principled and tedious".

Scarabia

Jamil Viper

Although their relationship, on Crowley's part, appears to be a neutral, Jamil has no sympathy for the Headmage. Much of this antipathy, in fact, likely stems from personal reasons, as Crowley is the person who agreed to admit Kalim into the NRC and his promotion to Housewarden in exchange for a generous donation from the Al-Asim family.
In Book 5, Jamil whispers a sentence in which he states that he suspects that Crowley accepted a bribe for Kalim's enlistment, however even the boy isn't sure.
Despite Jamil's blatant disdain for him, the two have a surprising amount of overlap as seen in Fairy Gala, Spectral Soiree, a flashback to earlier in the year, the VDC period and in a vignette where Crowley entrusts MC, Sebek, Grim and Jamil to prepare everything for the upcoming ceremony.

Kalim Al-Asim

Kalim is one of the rare students who does not feel contempt for him, on the contrary. In one vignette he decides to inaugurate a banquet in his honor when the Headmage shows interest in the local cuisine of his town. 
In the end, enthusiastic, Kalim invites Crowley to visit the Scalding Sands.
Later he is scolded by Jamil for his sudden decision to throw a party and ask permission before doing anything.

Pomefiore

Vil Schoenheit

Crowley has shown a greater personal interest in Pomefiore and the extension could also be addressed to Vil. When he sees Vil at the beginning of Halloween, Crowley is speechless: it's implied that his surprise is due to the fact that Vil is covered in glitter and it's no secret that the Headmage loves shiny things.
Crowley is delighted with his decision to have Vil take over the VDC's production after seeing the team's rehearsals. On the contrary, Vil shows no particular sympathy for him.

Rook Hunt

Rook may be one rare students who show no particular disdain for him. During Phantom Bride, in fact, Rook a flattering poem for Crowley.

Ignihyde

Idia Shroud

It's unclear how Crowley sees Idia, but it is widely possible that he doesn't have a flattering view of him. Idia, on the other hand, has never been shy about showing his genuine sense of dislike, just like most students.
In the Fairy Gala event, he even goes so far as to call Crowley a "presumptuous adult who dumps unpleasant work on his students." In Glorious Mascquerade his dislike of him is reaffirmed, when he saying that the Headmage could get sued for sharing personal information on his students to Rollo Flamme.
Idia is one of the characters who comment on the futility of the exhausting, but famous assemblies for which Crowley is given much negative credit. For once, Vil agrees with him.

Ortho Shroud

They have a cordial relationship, although Ortho in Phantom Bride threatened Crowley to destroy the school with his technomantic beam if they didn't find a way to save his brother.

Diasomnia

Malleus Draconia

Their lack of real interaction gives no way of knowing what they both think of each other. But Crowley is famous for never remembering to invite Malleus to any meeting, event, or conference.

Night Raven College Staff

Divus Crewel

He and Crewel seem to get along well. Crowley greatly appreciates Crewel's sense of style, wishing that one day he could get an outfit customized by him. According to Crewel, the Headmage is very busy dealing with one matter or another for the student body, but it's unclear what he's actually doing most of the time.
Crewel shows great curiosity towards him and would like to know something more about his figure, but Crowley doesn't seem inclined or interested in sharing details.

Mozus Trein

Trein and Crowley have been shown to have divergent personalities and principles, but they seem to share a good relationship, as the two often have tea together. However, he doesn't get along well with Trein's cat, Lucius.
Their relationship tends to take a sharp turn when Crowley does not display proper or unimpeachable behavior, and this may cost him a cold scolding from Trein. In a voice line, Crowley, states that Trein reprimanded him for a full ten minutes after he was ten seconds late to a meeting.

Their greater sense of contrast, however, can be well evidenced in the management and care of students, beyond behavior. Unlike the Headmage, in fact, Trein feels a strong sense of responsibility for students and is willing to protect them whenever necessary. In contrast, Crowley prefers to entrust problems to his students, hoping for their success and cohesion.
Their camaraderie, however, may be much more solid than proposed at first glance. When Crowley is arrested by S.T.Y.X immediately relies on Trein to manage and care for the college in his absence. This may insinuate that Trein is second in command after the Headmage.

Sam

The two have a good relationship. His abilities to always have everything in store leads Crowley to suspect that he may have some form of precognitive ability, but the extent and/or limits of Sam's magic are unknown.

Crowley's current dream is to get Sam to say that something is out of stock. For now it has always failed.
On the other hand Sam considers him a very mysterious person and, at the same time, too talkative for his tastes. He claims, in fact, that he wouldn't mind listening to him if only Crowley was a generous customer.

Ashton Vargas

The two have a positive relationship, although Crowley admitted that his excessive enthusiasm sometimes discourages him. Vargas has never seen Crowley without a mask and encourages MC to politely ask him to do so, even if they fail. According to him, Crowley is a "good-natured boy".

He seems to be taking into consideration Vargas' suggestion that they strength the students' muscles by changing the fabric of their uniforms into something much heavier.