Chapter Text
♡-Riddle Rosehearts-♡
♡-Yandere Type -> Controlling, Obsessive
♡-What are their main traits?-♡
Controlling -> He's actually surprisingly more lenient than one would expect him to be (this stems from him not wanting to treat you as strict as his mother treats him), but he's not going to let you run around like a wild animal. Even after his Overblot made him re-evaluate the worst of his strict behavior, he still values rules and order very highly. He is of the belief that he knows what's best for you, and has no qualms expressing that belief in a multitude of ways, whether it be creating a schedule for you to follow or curating your meals for you.
He's very demanding and has high expectations for you because it's his own twisted way of looking out for you. He justifies it to himself and to others as just wanting to provide you some structure in the strange new world that you're now living in. However, he is a lot more forgiving of your mistakes than he is with anyone else. Half of it is out of affection for you, and the other half is because of your situation. He rationalizes to himself that you're bound to make mistakes because you're from a world without magic, something that he's been utilizing every day for the majority of his life. When others point out his obvious favoritism, he vehemently denies anything of the sort, claiming that you simply make less mistakes than everyone else, whether or not you actually do.
Self-Righteous -> Riddle is the very definition of the phrase. Whenever his mother forced him to do something in his childhood, she would justify it by telling him that it was for his own sake, and that has heavily affected his outlook on life and how he treats people. Riddle does not know how to convince people to do things, because his mother never negotiated or reasoned with him throughout his childhood. In his mind, force is the only way to persuade people, and this viewpoint makes him think that he's doing the right thing by dictating your life.
♡-What would they utilize against their obsession?-♡
His position as a Dorm Leader and his magic. He's able to brush off many students who try to object to his treatment of you. If they ignore his warnings and lackluster explanations, he will very quickly lose his temper and start shooting around "Off With Your Head" to anyone who questions his relationship with you. If they're a member of his own dorm, he'll assign extra chores, make them do lines, or even write full-on essays to get his point across.
If Crowley, a teacher, or another Dorm Leader questions him, he'll claim that he's only trying to teach you how to be a responsible prefect yourself, especially with that rambunctious cat of yours. Speaking of Grim, Riddle's not above collaring him when you break rules, stray from your schedule, or object to his controlling behavior one too many times, since he can't exactly take away your magic if you don't have any. He'll only un-collar Grim once you've properly apologized.
♡-Do they get jealous? How do they deal with it?-♡
Despite his vehement objections to any accusation of it, he absolutely does. He is deeply insecure about a multitude of things, and this insecurity rears its ugly head when he thinks that you've been spending a little too much time with other members of the student body, especially ones that have what he lacks. For example, Jack, who is tall and strong, or Kalim, with his carefree way of running his dorm. He deals with his jealousy by trying to monopolize even more of your time, and justifying to himself about why he's just as good, if not better, then the person he was jealous of. Sure, Jack is muscular and tall, but that's not everything! Riddle has the best grades of his year, and actual magic is much more important to a mage. Sure, Scarabia's dorm members seem so much more carefree and relaxed. but they ranked last in exams and the Magift tournament! Riddle's way of running things is much more beneficial and efficient in the long run.
♡-How self aware are they?-♡
A little bit, but not enough to feel seriously guilty about the way he's dictating your life. As stated before, Riddle thinks that he's absolutely in the right in treating you this way, because he's trying to help you be the absolute best you can be.
♡-What kind of future do they want with their obsession?-♡
He is both terrified of introducing you to his mother and desperate for her to approve of you. Whether or not he's able to break away from her by the time his schooling comes to a close, he knows he wants you with him, no matter what. It is a deep desire of his to get you to transfer to Heartslabyul, but would never object to what the Dark Mirror has to say, as he views it as another rule that you can't join a dorm. He will satisfy this desire by constantly making you spend time at Heartslabyul, setting several of the activities he puts in your schedule there and having you attend every single Unbirthday Party. He'll visit campus as often as possible in his fourth year and visit you as often as he can in yours. If you're looking to have a smidge more of freedom in your life, now is the time to do it, because now is the only time he is unable to constantly make sure you're following the schedule he made for you. After you graduate, he will demand that you move in with him. He will attempt to justify this as further looking out for you, seeing as you have barely any knowledge of Twisted Wonderland outside of NRC, and believes that you would be completely lost if you were to be independent.
♡-> "Here's your schedule for today. After classes, you have an hour of independent study in the library, but after that we'll take tea and have a nice game of croquet- don't look at me like that. You know I'm only trying to make you well-rounded."
♡-> "I know what's best for you. I'm teaching you how to conduct yourself, like how the Queen of Hearts did for the little girl who fell into Wonderland."
♡-> "Hmph. I guess his strength is somewhat impressive to behold, but magic is much more important to a mage, and I'm always in tip-top shape in all of my classes."
♡-Trey Clover-♡
♡-Yandere Type -> Caring, Manipulative
♡-What are their main traits?-♡
Coddling -> It's really no surprise at all. Trey takes his position as an upperclassman very seriously, and will often baby people around him, but he'll be especially bad towards you for a few reasons. He is particularly soft on first years, and not only are you a first year, you are a magic-less first year, who comes from an entirely different world, stuck in a school full of students who have what he'll describe as "colorful" personalities.
Because of this, and his affection for you, he'll treat you as if you're completely helpless. He'll constantly walk with you in the halls, eat lunch with you, carry things for you, help you down stairs or high places, hold doors open for you, and the like. He'd like to send food to Ramshackle every day (because Sevens knows what you're eating with the meager food budget Crowley gives you), but will hold himself back, as it would draw attention to him. If others were to notice that he was being more caring to you than to anyone else, he would try to brush it off and say that he just thinks you could do with a little extra help. He'll take a peek at your class schedule and would ask Crowley if he could rearrange his own schedule, under the guise of wanting a change of pace.
Manipulative -> Like Riddle, Trey believes that he knows what's best for you, but unlike Riddle, he wouldn't force you to follow a schedule, eat in a particular way, or take away certain things until you do as he says. One because, it's just not his style, and two, it would draw quite a bit of attention to Trey and his relationship with you, attention that would be very inconvenient to him and his goals. Trey would much rather prefer to subtly "encourage" you to do what he says. He thinks "manipulate" is such an ugly word. He prefers the term "gentle guidance". If he thinks your friends are getting you into too much trouble, he'll casually bring it up in conversation. He'll tell you that you're so well-behaved and bright, you must get tired from them dragging you into messes all the time. He's trying to make you think that your friends are holding you back, so you'll drift apart from them and go to him, where he'll convince you that it's much safer and smarter to stay by his side and let him take care of you.
♡-What would they utilize against their obsession?-♡
Your situation and the way others see him. As stated above, you're a defenseless, magic-less person with no knowledge of how the world you've been cast into works. This makes it worlds easier for Trey to manipulate you into thinking that he's only trying to help you. (It also makes it easier for him to convince you to move in with him after you graduate, but we'll get to that)
Trey is a calm, conscientious, and rational person, and most of the student body sees him in this way. He's often called a pushover, but even this works to his favor. Nobody would see the concerning nature of his relationship with you unless they were extremely observant or looked extremely closely. It's how he's able to brush off other people so easily. Typical Trey, always babying the first years. Typical Trey, always spoiling people rotten with food and treats.
♡-Do they get jealous? How do they deal with it?-♡
He can get a little jealous, on occasion, but he's nowhere as bad as Riddle or Cater. He'll handle it as he always does, manipulatively. He'll "casually" mention some frightening or embarrassing factoid, make subtle digs at the person's character, or try to convince you that the person's intentions with you are less than pure.
♡-How self aware are they?-♡
Quite a bit more than Riddle. He's taken aback about how much he's thinking about you, about how much more he wants to coddle you than others, about his urges to keep you with him. He does feel a little guilty about manipulating you, but settles the guilt by telling himself that he's just taking care of you.
♡-What kind of future do they want with their obsession?-♡
After the two of you graduate, he'll try to convince you to move in with him for the same reasons Riddle would force you to. Once he's gotten you to live with him, his coddling will crank up several notches, but he tries to be as subtle as he can about it. He'd rationalize this to you by telling you that you shouldn't go out on your own because you're not familiar with Twisted Wonderland at all, you might get lost, and that he already did all the cooking back at school, so it doesn't have to be any different now that you've graduated. Trey will encourage you to focus on your hobbies, because you don't need to worry about getting a job. He'd be happy to provide for you.
♡-> "Good afternoon, Prefect. Sorry to barge in like this, but I made you some sandwiches and a pie. No, no, don't thank me. It's really nothing at all."
♡-> "Wake up, class is over. Yes, you fell asleep. Don't worry, I took your notes for you. What would you do without me? Ha, I'm just kidding."
♡-> "I know it's really none of my business, but I heard that he beat someone up for being magic-less one time. I just don't want to see you hurt."
♡-Cater Diamond-♡
♡-Yandere Type -> Possessive, Obsessive
♡-What are their main traits?-♡
Obsessive -> Night Raven College's resident Magicam addict will constantly stalk you on it. If you don't have an account, he'll practically beg you to make one, going on about how you'll love it on there and how much fun it is. If somebody points out or questions him about how desperate he is for you to be on Magicam, he'll become extremely embarrassed and try to deflect by claiming that he just wants you to have as much as he does on there. He's not above practically snatching your phone from you, going, "Here, it's super-duper easy to make one! Let's do it together!" and basically making the account for you.
Even if you never post, he'll still DM you about every 10 seconds. He'll yammer on about anything and everything as long as it means you'll hold a conversation with him. If you tell him to stop DMing you, he'll play it cool but will internally freak out. He'll over-analyze every message you send. If you post at all, whether it's only occasionally, semi-regularly, or just as often as he does, he'll cyber-stalk you every single day. He'll convince Idia or Ortho to install a custom notification on his phone that's specifically for your account, will constantly look at your posts to give himself a dopamine boost, and would even print out one (or several) of your posts to hang on the wall next to his bed so can look at them while he tries to sleep.
He is extremely knowledgeable about your interests and what you like, and likes to keep the focus of the conversation on you. This is because he loves to hear what you have to say about almost any given subject, and because when his sisters interact with him, they always make everything about themselves, give him gifts that are centered around their interests, not his, and generally don't bother to figure out what he wants and what he likes. He also finds them extremely overbearing, so if he catches himself acting even a little bit suffocating towards you, he'll reel back so fast that it's jarring.
If you were to steer the conversation towards him and his interests, he would feel very conflicted. On one hand, Cater would be absolutely ecstatic, because it means you're at least interested in him enough to want to know more about him. On the other hand, it means that there's a chance that you won't like what you hear and you won't want to associate with him anymore. Cater treats every conversation like a balancing act; don't completely center the conversation around himself so you don't feel overshadowed by him, but don't act annoyingly secretive and frustrate you.
Insecure -> While Cater is deeply worried about what you think of him, the majority of his insecurity stems from the instability of most of his relationships. He's gone through more schools than he can count on one hand, and is afraid to let anyone get too close, because he's trying to protect himself from being too hurt when they graduate and go their separate ways. And then he meets you, and he loves you. But you're not even from the same world as him, and you're going to leave him, too, when Crowley finds a way to get you back to your world. Cater tries to make himself as appealing as possible to you in a desperate attempt to keep you with him.
♡-What would they utilize against their obsession?-♡
His talkative nature and his presence on Magicam. He will frequently talk about anything that might keep you even a little interested in the conversation, and will lie about aspects of himself to try and impress you. He'll dig up dirt and talk shit about a rival all day long.
If you upset him enough, he'll vague about you to his followers and show you the post and its comments to try and make you feel guilty.
♡-Do they get jealous? How do they deal with it?-♡
Like Riddle, he pretends that he doesn't, but he absolutely does. Cater is one of the worst ones out of the whole cast. His insecurities flare up horribly when you even mention someone else, and he'll try to immediately steer the conversation away from the topic of whoever you mentioned. If you persist, Cater will start digging for dirt right away, if he doesn't already know any. He'll start shit-talking, and might send some of his clones out to create an embarrassing situation and get a picture of it to show to you.
He'll make a super cringy video of him looking sad while the Twisted Wonderland equivalent of Joji plays in the background and tag you in it, with an on-the-nose caption about betrayal or abandonment.
Internally, he'll be crying and screaming. He'd try to adopt the traits of the person he's jealous of while he's around you to try and present himself as a better version of them, and will constantly fish you for compliments.
♡-How self aware are they?-♡
More so than Riddle, but less so than Trey. Cater knows that the behavior he's exhibiting towards you isn't the most normal, but he just wants you to stay, and he doesn't care what he has to do to achieve that.
♡-What kind of future do they want with their obsession?-♡
Cater would very much like to find someplace to settle down with you permanently. He's had enough moving for one lifetime. He'd probably choose a house in a popular area, so he can focus on his Magicam hobby better. He'll get you to move in with him by telling you that his house is a super stable place to stay, and that it'll be easier for you to live in Twisted Wonderland when you only have to pay half of the bills.
♡-> " Never fear, Cay-Cay is here! Let's take a picture for Magicam, just the two of us~"
♡-> "Prefect, Prefect! Did you see the post I sent you? You didn't respond so I came to show you in person~"
♡-> "Ugh, well, I guess his hair is okay, but I heard he like, had this accident in alchemy that turned his skin blue."
♡-Ace Trappola-♡
♡-Yandere Type -> Manipulative, Possessive
♡-What are their main traits?-♡
Manipulative -> It should come as no surprise. Ace is already a very dishonest person and horrible cheat, and will not tone it down when it comes to you at all. Can you blame him? You're just so easy to fool! He's horrible when it comes to guilt-tripping and emotional blackmail. He'll complain about how much effort he's putting into your friendship with no reciprocation, and will make you feel guilty for not letting him monopolize your time. He'll distract you with magic tricks whenever he feels like you're starting to figure out his underhanded actions or when he doesn't want you to notice something that he's doing.
It's a bit of a push and pull for Ace. He's terrified of you figuring out his lies and just how much he cares for you, but also wants to spend every waking moment with you. He'll go from complaining about how little you give to your friendship with him, to saying that he's just letting you tag along. He'll shamelessly try to flatter and butter you up one moment, but tell you that you're lucky to have him as a friend because you're unremarkable compared to the rest of the student body the next. If someone calls him out for his cruel comments, he'll deflect by insisting that it was a joke or claiming that the person calling him out is too sensitive.
Caring -> It might come as a surprise to some, but Ace likes you a lot more than he lets on. He'll try to be around you as often as he can, will claim the seat that's right next to yours in every class (even if he has to bully someone out of it), will walk to every class with you, will eat as many meals as he can with you (and share them), and will constantly find excuses to go to Ramshackle. He'd rather die than admit it, but he worries about you almost all of the time. He'll show off his magic and card trick skills, but will get huffy if he doesn't think that you're impressed enough. Ace will implore you to join the basketball club at least twice a week, telling you that you have solid talent and will yammer on about how many games the team will win with an extra player.
Ace secretly values your opinion more than anyone else's and will try to hide his utter dejection whenever you don't give him the response he wants to something. If he gets desperate enough, he'll start fishing for compliments.
♡-What would they utilize against their obsession?-♡
His manipulative attitude. Though it does make him feel a little guilty, he tries to make you feel helpless, confused and alone so you'll stay with him and let him monopolize your time. If someone tries to confront him on his behavior, he'll lie and lie and lie to get his ass out from under the hot seat.
♡-Do they get jealous? How do they deal with it?-♡
Very much so. Ace will get super huffy and pissy whenever he thinks you're paying too much attention to someone else. He'll loudly complain about something to get your attention, and is not above pulling away from the person if it's a situation where he's able to. He'll also shamelessly lie through his teeth about whoever he's jealous of, and will double down if he's called out for it. He also likes to distract you with flashy magic tricks or by showing off something he thinks he's good at.
♡-How self aware are they?-♡
Ace does feel a little guilty and conflicted about his deception, and is surprised by his sudden, obsessive feelings for you, but he ultimately doesn't care. At the end of the day, he doesn't really view it as toxic behavior, but being proactive about getting what he wants.
♡-What kind of future do they want with their obsession?-♡
He's not really thinking too intensely about the future, because it's only yours and his first year, after all, and planning ahead really isn't his style. However, he does want to continue going to all the same classes with you, and will try his best to convince Crowley to put the both of you in the same internships in your fourth year.
He also wants to introduce you to his family! His parents and grandma, yes, but especially his brother. He views you and his brother as the two people he's closest to, and would be delighted if you got along.
♡-> "Hey, Prefect! Come over here! I wanna show you this trick I just learned! Don't you think it's cool? Don't you?"
♡-> "Huh? You need to copy my homework again? Pfft, you're useless without me! Ah- come on, I was just kidding!"
♡-> "Pfft, he's not that cool! He's a total jerk! What? He is! He pushed me out of the lunch line last week!"
♡-Deuce Spade-♡
♡-Yandere Type -> Protective, Irrational
♡-What are their main traits?-♡
Protective -> Deuce can't help it, really. He's seen and experienced first-hand how cruel, rambunctious, and malevolent people can be, especially in Night Raven College. He desperately wants to keep you safe from all the dangers at school and the world, and will go to extreme lengths to achieve that. Deuce will immediately know if someone has less than pure intentions with you, and will even suspect innocent people if he perceives something that's slightly off about them. If someone tries to mess with or harm you, Deuce will barely be able to hold himself back from beating them into a pulp. He'll settle for threats and demonstrations of his strength, only when you're not around. He'd rather die than have you see him like that, and would feel horrible if he scared you. He would frighten the offenders enough to make them apologize to you or to never look your way again.
Deuce deeply craves your approval and admiration, and would throw himself into anything he does that would impress you. If you admired his track and field skills, he would start training every day, and wouldn't feel confident in a race until he knows that you're in the crowd. If you liked his dedication to school, he would study 'till the early hours of the morning, and would completely throw himself into his schoolwork.
Irrational -> Deuce convinces himself that the two of you were meant to meet, that you're supposed to spend the rest of your lives together, that he's meant to keep you as safe and happy as possible. He thinks that threatening anyone who looks at you wrong is for the greater good, and will be generally unrepentant and unapologetic towards whoever he perceives to be a threat to your safety and happiness. Even if someone ends up hurt, it doesn't matter to Deuce at all the moment he reminds himself that it's all for you.
He will vehemently defend any and all of your flaws to anyone who's foolish enough to bring them up around him, and won't stop arguing until the other person backs down or leaves. Deuce is the number one advocate for your character, and people around him learn quickly not to mention you around him because he'll start going on and on about how good of a friend you are, and won't stop until somebody tries to make him, which he will interpret as a personal insult towards you.
♡-What would they utilize against their obsession?-♡
Deuce would never intentionally use anything against you or try to manipulate you, but he would unintentionally utilize his past experience as delinquent, especially when he's scaring off potential rivals or threats.
♡-Do they get jealous? How do they deal with it?-♡
He does, but he doesn't really register it as jealousy. He sees you talking to somebody else, feels something dark swirling inside of him, and comes to the conclusion that his instincts are trying to let him know that the person he's jealous of is dangerous and he needs to get you away from them immediately. He'll pull you away from them, start questioning their intentions with thinly-veiled suspicion, or will just outright tell them to leave you alone.
♡-How self aware are they?-♡
Not at all. He fully believes that his overprotective behavior is only keeping you safe. And will think almost anyone calling him out or criticizing him about it is trying to hurt you or take you away from him. He'd be a little more willing to listen to authority figures on the subject, but will ultimately come to the conclusion that they just don't understand the danger you could be in without him protecting you.
♡-What kind of future do they want with their obsession?-♡
He wants you to complete school together, introduce you to his mom, and get you to move in with the both of them. His mother is the only one he would trust to keep you safe while he's out becoming or being a magical enforcement officer. He'd want you to stay at home, because he'd be too worried about dangerous work conditions, mean co-workers, exploitative bosses, and the like to let you get a real job outside of the house. However, he'd be comfortable letting you find work online, because he'd be able to tell immediately if something was wrong.
♡-> "We get along so well, I'm pretty sure that we were meant to be BFF's... Eh? 'What do I mean?' Um, well... Just- just forget I said anything..."
♡-> "Ah- I'm sorry, I'm so sorry! I didn't mean to blow up at them like that! It's just... they just felt suspicious, is all..."
♡-> "You should come to my house for the holidays this year. It's a lot warmer than Ramshackle, and my mom would love you."