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Twisted Wonderland Senarios

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Leona was going on about his day when he decided to skip the next class since there was nothing of importance going on, he already knew the subject well plus he was keeping count of how many days he skipped so he didn't have to stay back a year again. He decided to take a nap in the botanical garden, in his usual spot behind a big tree with a lot of plants with a strong fragrance but as he got closer he saw someone taking a nap there. He was a bit annoyed that someone had taken his spot but then he realized it was you. His first thought was how adorable you looked as you slept, his next one was why was his first thought “Y/N looks cute” no he should be finding another spot to nap before his next class started, wait why was he about to look for somewhere else to nap if he could just wake you up and kick you out? You stirred in your sleep and he got startled by it, afraid that he had woken you up, oh so now he was afraid of waking you up he thought what had gotten into him why was he like this. Then it hit him that this wasn’t the first time he’s had these thoughts. He shared half of his sandwich with you when you gave your food to Grimm and had nothing to eat. When you were struggling in professor Crewel’s class and he helped you study, he realized he liked you. “Leona? What are you doing here” You had woken up “I could ask you the same Y/N but let’s not focus on the details, move I want to take a nap” you got up to leave, “I said move not to leave I don't mind sharing the space if it’s you” For a moment you swear you could see a faint blush on his face

Ruggie

You saw Ruggie running around school as if he was looking for something, he finally stopped for a moment so you approached him “are you looking for something ruggie?” “Ah Y/N I’m looking for Leona, there’s a dorm leader meeting and he has to attend it but I can’t find him,” you thought for a moment “Oh I saw him taking a nap at the botanical garden behind the big tree at the back”ruggie smiled” thank you I’ll go check there” poor ruggie you thought maybe you should get him something to get his energy back up after all that running he had done. Lunchtime had come and Ruggie was rushing to get Leona’s special sandwich when you called out to him “Ruggie!” running up to him you handed him a drink “Here, to replenish your energy” He blushed “for me? Thanks” “Don’t worry you are very dear to me so...I just wanted you to have something, especially with how hard you work" there was a bit of silence between you guys, Ruggie didn't know how to react so he just said something about having to give Leona his lunch and left he could feel his heart racing so fast once he got to Leona and gave him his lunch his heart was still racing. Leona glanced at him and noticed something was different, ruggie just handed him his lunch without saying anything and he could see him blushing " did something happen with Y/N? Judging by your looks...did you finally confess?" wait what finally confess? He thought about it for a bit, yeah that would explain how fast his heart is racing now, he liked you, he just didn't realize it until now. “Well Leona I must go now” Leona just waved him off “now he must really be going to confess”

Jack

Jack doesn’t have an idea of how he wants his future partner to be like, he figures that he’ll know when the time comes. He does know that when he does it will be forever just like his parents and grandparents. He was visiting them during school vacation, that’s why he was now thinking of the future of his love life. He watches as his parents make breakfast together and remembered how he helped you in at the Monstro lounge to save your friends because you couldn’t leave them like that. He admired that about you. Later on, he saw how his dad played along with his younger siblings and that reminded him of how you often play along with grim. Laying in bed he wondered why he was thinking of you throughout the day, this wasn’t the first time it had happened either... could it be...that you are his ideal partner? He blushed at the thought and his heart raced.