Riddle Rosehearts/Background

Childhood
Riddle was born and raised in the Queendom of Roses. Both his parents are magic doctors, but his mother seems to be more well-known. Riddle's mother was the most respected individual in their town, which contributed to the way she raised Riddle.

Riddle's mother raised him and taught him from a very young age to be a powerful magic user, like herself, with every aspect of Riddle's life controlled by his mother: Clothing, diet, his friends, etc. Riddle's mother especially put emphasis on Riddle's study schedule, reminding him multiple times that studies are the most important thing to do and that playing is a pointless activity.

One day, Riddle was studying alone when he saw Trey and Chenya outside his house, asking the boy what he was doing. Riddle told the boys that he was studying under the orders of his mother. Trey and Chenya then invited Riddle to play a game of croquet together outside. Initially hesitant, Riddle refused the offer - he was not allowed to do so, after all. However, after some convincing, Riddle finally played with the duo. Since playing together with Trey and Chenya was a really fun experience, Riddle would sneak out of his study time unbeknownst to his mother to play with them.

While playing together, Riddle stated to Trey and Chenya that he had never tasted strawberry tarts before because sweets are prohibited by his mother to ensure he does not exceed his daily caloric intake, much to the surprise of his friends. Trey and Chenya wanted Riddle to try his first tart, and the two then brought Riddle to Trey's popular family-owned cake shop. There, Riddle tastes the strawberry tart, and loved it so much that he ate until he lost track of time. He was then found by his angry and upset mother, and dragged back home.

Back in the house, Riddle's mother harshly reprimanded the distressed Riddle, who begged and cried to his mom for forgiveness. His mother then reduced his break times for study hours ever since. In addition, Trey and Chenya were banned from ever interacting with Riddle and were not allowed to enter the Rosehearts' residence again. As time passed, Riddle spent his days doing nothing but studying and following his mother's orders.

1st year
A week after enrolling in Night Raven College, he did not like how lax the previous Heartslabyul dorm head was with enforcing the rules. So he challenged the previous dorm for his position and won and became the current Heartslabyul dorm leader.

Main Story (2nd year)
For his first entrance ceremony as the new dorm head of Heartslabyul, he and the members prepare a welcome party for the new students later that evening. He is quick to scold a member for asking for clarification about the table clothes and threatens to have his head for not remembering the rules, by which Trey persuades him to calm down and lets the student go.

Prologue
During the opening ceremony, Yuu's presence followed by the chaos caused by Grim prompts Riddle and Azul to capture him. After they corner Grim, Riddle uses his unique magic to collar him, sealing his magic. After that, Riddle becomes angry that the entrance ceremony didn't go perfectly because of freshmen leaving during the sorting and Grim causing chaos. Cater and Trey find out that the roses in Heartslabyul aren't the correct color for the dinner party, so they find a way to distract Riddle while Cater fixes the roses as to not worsen his mood.

Episode 1
Riddle catches Ace late at night in Heartslabyul's kitchen eating one of the tarts from the fridge. Because it breaks a rule of the Queen of Hearts, he punishes him with his unique magic and collars him. The next day, he collars three more students for missing the morning roll call. During lunch period, Riddle walks in on Ace speaking harshly about him and referring to him as a tyrant behind his back, promptly scolding him for it. He then turns down Ace's request to remove his collar, stating that he hasn't learned his lesson. Because Ace is still a first year, he assures him doesn't need to use magic in classes just yet. He cites a rule of the Queen of Hearts to them to not idle around after finishing their lunches and prepare for their next class, then leaves to buy sugar cubes from the school store because of another rule that requires him to drink tea with it after a meal. Later in the evening, he collars another ten students for breaking a rule that forbids drinking lemonade with honey after 8pm, which agitates the dorm members further about his strictness.

On the day of the Unbirthday Party, Riddle is welcomed by the dorm members then remarks on the perfect state of the party with everything following the traditions. However, his mood is ruined by Ace who presents to him a mont blanc. This breaks another rule of the Queen of Hearts that forbids bringing a mont blanc to an Unbirthday Party. Despite Trey admitting that he was the one who helped them make the mont blanc, Riddle dismisses it saying that the fact it was brought to the party was the problem. When Yuu, Ace, Deuce and Grim confront him about the absurdity of the rules, they are promptly collared then thrown out of the Unbirthday party by Trey and Cater.