Platonic Twisted Wonderland Adult Fem MC with Riddle, Ruggie, and Jamil
In this scenario, MC comes to NRC as a full adult, 9-5-type experience. You would still come in with Grim and become a ‘first year,’ sort of like how Malleus and Lilia are fully grown but technically third years. And you somehow become more of an older-sister/mother-figure to most of the boys. But some of them are way more than others (that definitely need one). I’m thinking in particular with Riddle, Jamil, and Ruggie. Also, probably Silver, Leona, Idia, and Cater. You could honestly argue that most of them need one, since let’s be honest, a lot of them need therapy.
This part includes Riddle, Ruggie, and Jamil.
-> Floyd, Jade, Epel, and Idia here.
-> Leona, Malleus, and Sebek here.
-> Cater, Silver, and Crewel here.
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Warning: This is my first-ever headcannon list, and I have just gotten back into the game after two years, so I apologize if it’s a little OOC.
We know how he is with his mother, so he is probably one to benefit the most from having an older female role model.
After the aftermath of Book 1, you reach out and try working with him to unlearn some of the toxic behaviors his mother taught him. For example, the extreme diets his mother put him on, the continuous studying without breaks, etc. I imagine MC taking Riddle to places he’s likely never been before, such as an amusement park or aquarium.
I would say it takes a bit for Riddle to warm up to MC just because he’s not used to being vulnerable, but once he does, he is ATTACHED. Like will show up at Ramshackle and ask you to come to whatever party is happening in Heartslabyul. You are the first to be invited to anything Riddle plans now.
Since you are not from this world and aren’t familiar with the history, Riddle wouldn’t mind teaching you all about it. Be prepared for a four-hour lecture on the history of the Queendom of Roses. He also would love to hear about your world, so he will bombard you with questions about living in a place that is magic-less.
Don’t be surprised when you find random gifts given to you from Riddle. Such as free textbooks, clothes, and other stationery items. Outside of school supplies, he will shyly give gifts of things he would like to try with you, such as a board game he overheard Azul and Idia playing.
I think out of all the boys, he will likely be the clingiest and also see you as a mother figure that he didn’t get growing up. Additionally, with this MC, he is the first to get attached if we’re following the main storyline. He will deny this to Ace, who keeps teasing him for constantly wanting to be around you. Also, Riddle will be checking up on you through Deuce and Ace (mostly Deuce because of Ace's teasing).
This one is a bit more complicated since he technically does have an older female figure in his life (his grandmother), but he is often the one having to care for others and not the other way around.
This relationship will likely form after Book 2, when we learn Ruggie’s backstory of living in the slums of Sunset Savannah.
Just like Riddle, he will take a while to actually be vulnerable. Compared to Riddle, though, he has no shame in opening up with his past; it’s more of the emotional distance he keeps with the other students at NRC.
With him, though, gift giving is his love language and the one he likes receiving the most (even platonic!). So if older MC starts gifting him things such as food, extra clothes (they somehow got?), literally anything, he will be very happy. Of course, this comes from his survival instincts, where he feels forced to hoard all of his resources. But this will slowly get him to trust MC and see them in a positive light.
I imagine MC gifting Ruggie food in particular because this one is probably the most meaningful for him. In this scenario, MC is decent at cooking since she has been cooking for herself for a bit. Ruggie isn’t picky, so even if you aren’t the best chef, as long as it’s edible, he will love it.
The real test is if Ruggie is giving MC food back. That is his ultimate form of affection because of how meaningful food is to him. We can see this in Book 4, when he brings home food to the kids back home. At least by the end of Book 3, Ruggie has some worries for MC. If he finds out you’re missing meals, he will find a way to get you food; he will steal Leona’s credit card if that’s what it takes!
MC probably falls into some kind of coddling with Ruggie, which he does not mind at all. At first, he’s a little weirded out, but once he realizes you’re pampering him without wanting something in return, he loves it. You might do things for him, such as brushing his hair (be careful with his ears), or taking him to get his nails painted for the first time. Of all the characters in TWST, he has the least shame; hell, he might even boast about this to the other characters. Which, I cannot tell if Leona will hate or love this, lmao.
He is definitely clingy, just maybe not Riddle levels. Unlike Riddle, he has no shame in showing affection, like putting his arm around you or straight up just climbing on you (doesn’t matter how short or tall you are, he wants a piggyback ride).
You are also helping him with his long-ass resume, which he very much appreciates. If you are in the corporate world, he will be using that to his advantage.
The kids back home send you homemade cards, and now you are in contact with like twenty different kids through Ruggie.
Like Riddle, Ruggie is checking up on you through Jack. Jack doesn’t mind but will often just tell Ruggie to go see you himself. This has caused a lot of bickering between the two.
Ruggie: “Just tell me if she’s been eating or not!”
Jack: “How would I know that? You can go ask her that yourself.”
Ruggie: “You are the one who has lunch block with her!”
Now Jack is asking you each time he sees you in school if you’re eating, which is embarrassing for him. But…Ruggie said he’ll run with him in the morning if he asks.
Jamil is going to take probably the longest time to open up. He’s been taught, like Riddle, that you cannot show emotions. However, now add in the fact that he didn’t even get ‘true’ childhood friends like Riddle did (Trey, Chenya) because he was stuck serving Kalim. Yes, Kalim saw him as a friend, but Jamil did not.
His parents have taught him that Kalim’s needs come before his own, so he’s still in the process of unlearning that. MC likely gets close with Jamil during Book 5. When they are all in Ramshackle training (Jamil, Vil, Rook, Epel, Kalim, Ace, Deuce), this is when you get closer.
Mind you, while this is happening, Riddle is sending Ace and Deuce to bring you a pie Trey made, and Ruggie is showing up asking about trying face masks together. This confuses everyone (besides Ace and Deuce), but especially Jamil.
Like, why are Riddle and Ruggie out of all people showing you affection???
For Jamil, acts of service are the most likely to get him flustered. MC is washing Jamil’s clothes (because Crowley finally got you a washing machine!), and you did not want smelly teen boys’ clothes in your house. Jamil at first was upset because he’s so used to doing everything himself, so he expected you to somehow mess up his laundry. But when he realizes you know how to separate clothes from whites and darks (you’re a grown adult), he is like, okay fine. But he still feels awkward about it at first.
If you keep cleaning up after his stuff, he starts to feel guilty and feels like he needs to do something back. But when you brush it off, he is even more appalled. You probably say something about not wanting dirty clothes in your house, and then he feels like you’re a mirror of him, haha.
Also, if you kill or take care of a bug near him, he will start seeing you as some sort of savior. In which case, it is now your job to handle bugs.
Unlike Ruggie, though, please don’t cook for him. Unless you are extremely talented in cooking, I would not bother. He will try your food because he does care about you, but he will be making a face…
Jamil is secretly competitive, so I can see him being the most likely of all of them to get jealous. Like, once he’s attached, oh, he is not letting Riddle tutor you better than him. He’s had to tutor Kalim so he can tutor anyone!
Poor Riddle is confused as to why Jamil is giving him death glares in the middle of Alchemy class. Now this is even being transferred into grades (against Riddle) because he doesn’t have to hold back with Kalim anymore.
The same goes for athleticism. Though Ruggie and Riddle do different club sports, he’s got to win at every basketball game. NRC is somehow going to the finals because of this, and Ace and Floyd are somehow locked in by some God given miracle.
Kalim, of course, is supportive of Jamil making some new friends, now that he’s allowed to be himself. But it’s a bit uncomfortable because Kalim knows he cannot show it due to their strained relationship. So Kalim allows Jamil to throw you a party without him being there (as an attempt to mend their relationship).
In this context, the party is your birthday party, and you can expect to have the most outlandish party. There are fireworks, elephants (how did they even get them?), dancing, many many gifts, a live band, and all of the Scarabia students celebrating as well.
If you’re more shy (ironically like Jamil), he will tone it down, though, and have a more private party with just the two of you.
Similar to Riddle, I imagine a lot of the things you do with Jamil might be more childish in nature. Sure, he’s been to places like the amusement park, but not without worries about Kalim’s safety the entire time. He might be tense at first, but I feel like he really likes rollercoasters.
Feel free to give me any suggestions for future parts!
