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 his mother's orders. 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. He challenged the previous dorm for his position and won to become the current Heartslabyul dorm leader. Riddle had his dorm uniform tailored to the same design as the first dorm head of Heartslabyul and wore heels, but he initially had difficulty in wearing them as it was the first time he wore high heels. Vil, who was the vice leader of Pomefiore at the time, found him resting in a quiet area in the school with blisters on his feet. He offered him a band-aid and was told the reason why Riddle chose to wear heels. The next day, Riddle came to his class to return the band-aid to follow a rule in Heartslabyul that states one must always return what was borrowed.

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

Prologue
Riddle was present in the opening ceremony for freshmen students as a housewarden. He found Ace's response to being called to the front unmannerly and expressed disappointment when he was sorted to Heartslabyul. The new students whispering among themselves made Riddle irritated when Sebek raised his voice to scold them. He found promise in this freshman and thought of putting him in charge of the first years. Sebek's sudden outburst upon being sorted to Diasomnia surprised Riddle. During the opening ceremony, Yuu's presence followed by the chaos caused by Grim prompted Riddle and Azul to capture him. After they cornered Grim, Riddle used his unique magic to collar him, sealing his magic. After that, Riddle became angry that the entrance ceremony didn't go perfectly because of freshmen leaving during the sorting and Grim causing chaos. Cater and Trey found out that the roses in Heartslabyul weren't the correct color for the dinner party, so they went to distract Riddle while Cater fixed the roses to not worsen his mood.

Episode 1
Riddle caught Ace late at night in Heartslabyul's kitchen eating one of the tarts from the fridge. Because it went against a rule of the Queen of Hearts, he punished him with his unique magic and collared him. The next day, he collared three more students for missing the morning roll call. During lunch period, Riddle walked in on Ace speaking harshly about him and referring to him as a tyrant behind his back, promptly scolding him for it. He then turned down Ace's request to remove his collar, stating that he hasn't learned his lesson. Because Ace is still a first year, he assured him he doesn't need to use magic in classes just yet. He cited a rule of the Queen of Hearts to them to not idle around after finishing their lunches and then prepare for their next class, then left 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 collared another ten students for breaking a rule that forbade drinking lemonade with honey after 8pm, which agitated the dorm members further about his strictness.

On the day of the Unbirthday Party, Riddle was welcomed by the dorm members then remarked on the perfect state of the party with everything following the traditions. However, his mood was ruined by Ace who presented to him a mont blanc. This broke another rule of the Queen of Hearts that forbade bringing a mont blanc to an Unbirthday Party. Despite Trey admitting that he was the one who helped them make the mont blanc, Riddle dismissed it saying that the fact it was brought to the party was the problem. When Yuu, Ace, Deuce, and Grim confronted him about the absurdity of the rules, they were promptly collared and then thrown out of the Unbirthday party by Trey and Cater. Riddle then stressed over the fact that they were now 15 minutes behind schedule. After the Unbirthday party later that day, he scolded another dorm member for not wearing pink while feeding the flamingos as per Heartslabyul tradition. After having him collared, he ordered the student to write a 5000 word apology and to weed the garden for a week before he could unseal his magic. He then ordered Cater and Trey to get the student out.

Ace and Deuce challenged Riddle to a duel the next day following their conversation with Headmaster Crowley and Trey in the library. Crowley asked Riddle to remove his magic-sealing collars which he followed, then told Ace and Deuce that it won't be long until they have them back on. Cater asked him about the afternoon tea that was traditionally held at 4pm because it was already past 3:30, by which Riddle responded that he wouldn't take too long dealing with the two. Riddle ordered them to take him on at once. When Crowley began the match, Riddle immediately collared the duo in less than five seconds.