Riddle was born and raised in the Queendom of Roses. His parents are magic doctors, but his mother seems to be more well-known. The whereabouts of his father is unknown. Riddle's mother raised him and taught him from a very young age to be a powerful magic user. She controlled every aspect of Riddle's life; clothing, diet, who Riddle can be friends with, etc. She especially put emphasis on Riddle's studying schedule, reminding him multiple times that studies are the most important thing to do and that playing is a pointless activity. Because of this, Riddle spent most of his childhood alone and spent it studying. But one day, he saw Trey and Che'nya outside of his house, who asked Riddle what he was doing. Riddle told the boys that he's studying, as his mother told him. Trey and Che'nya invite Riddle to play together outside, with the hesitant Riddle initially refusing the offer, but after some convincing, he agrees to play with them. Riddle states that playing as a child with Trey and Che'nya together was a really fun experience, and so he would sneak out of his study time unbeknownst to his mother and play with Trey and Che'nya. On another occasion, while Riddle was playing together with Trey and Che'nya, Riddle stated that he'd never eaten strawberry tarts before and didn't know the taste of them, as sweets were prohibited by his mother, much to the surprise of his friends. Trey and Che'nya wanted Riddle to try his first tart, and the two then brought Riddle to Trey's popular family-owned bakery, though Riddle was reluctant about it at first. At the bakery, Riddle tasted the Strawberry Tart, and loved it. He ate until he lost track of time, in which he was found by his angry and upset mother, and was dragged back home. Back in the house, Riddle's mother harshly scolded and reprimanded the distressed Riddle, who begged and cried to his mom to forgive him, but Riddle's mom didn't listen and thus made his studying time even more strict than it already is. In addition to the strictness of his schedule, both Trey and Che'nya were forbidden from ever interacting with Riddle and the two were to not step foot into Riddle's house. As time passed by, and Riddle spent his days doing nothing but studying and following his mother's orders, he adjusted to the harsh and strict life he had to live through. A year before this scenario takes place, Riddle was recruited to be a student in Night Raven College, and a week after he enrolled into the school, he became housewarden of Heartslabyul and has been fulfilling the role since then.