At the beginning of Book 4 Riddle goes to the hall of mirrors to return home with the rest of the students for winter break, and Grim describes Riddle as sounding “kinda defeated.” Ace follows with, “The housewarden’s got an extreme case of helicoptor parenting waiting for him at home. No wonder he’s not enthused about heading back.”
Trey apologizes for not being able to bring any cakes for Riddle during the holiday despite how they live nearby to one another as he is not allowed in Riddle’s home, and encourages Riddle to visit him at his family’s shop. Riddle responds, “I think…I’m going to try talking with Mother some. I don’t know if she’ll listen, but even so.”
It is possible that Riddle’s mother did not listen: in Book 5 it is revealed that Riddle was unable to visit the Clover family cake shop during the break.
In a flashback we see Riddle shift from calling his mother “Mama” to “Okaa-sama,” reverting to “Mama” during his overblot. In his dream Riddle again returns to referring to her as “Mama,” and we learn that she also refers to herself as “Okaa-sama” in reality, calling herself his “Mama” in his dream.
Riddle’s mother refers to him as “Riddle-chan” in his dream, and is delighted when he brings friends home with him (Trey: “…Unbelievable. His real-life mother would never react so happily if Riddle brought friends over”).
The students describe Riddle’s home of his dream having classical decor and windows that look out over a well-tended garden, similar to Heartslabyul. The living room walls are covered in family photos from experiences and vacations that never actually happened. Ace notices that Riddle is the only one in focus in any of the pictures and his parents are always blurry, but Chenya explains, “Isn’t that always how it is in family pics? The children are the center of attention. and the parents come second.”
There are no magic users in Riddle’s dream-family, with Idia observing, “We’ve got someone so immersed in their dream that their entire life has been rewritten from the ground up.”
Riddle of his dream hates studying and missing out on the fun things of the world.
After the living room floods with tea from the kitchen Idia suggests that there was never a physical equivalent of Riddle’s mother in the house to begin with, “and it was the house doing the talking the whole time.” Ortho asks, “This house is both a trap designed to keep Riddle locked up and immersed in his dream, and a vicious monster engineered to eliminate us since we’re trying to wake him up?,” and it is possible that this is also related to Riddle’s strictly controlled childhood: Idia reveals that in Riddle’s dream “the house itself is the darkness” and an unseen Riddle begins to cry that he wants out. Leona says that they will free him and Riddle responds, “But there’s no key…”
After explaining how every details of Riddle’s life had been predetermined for him by his parents Trey says that he completed every task that was laid out for him in order to please them.
During the Lantern event Riddle reflects on how the Princess in the Tower obeyed the witch whom she thought was her mother, “Despite her boredom with her day-to-day life and her yearning for the outside world.” Riddle says, “If I were to guess, perhaps the princess didn’t want to make the witch sad…”
After waking in his dream of Book 7 Riddle’s dream-Mother asks if he fell asleep as she read to him. Riddle responds, “If I fell asleep while you were reading to me, you’d yell at me so much, I’d wish I’d never woken up at all. But your style of education is what made me the strong, exceptional individual l am today.”
Riddle says that his mother has never once called him anything so endearing as “Riddle-chan” and says, “How dare you impersonate my fearsome, awe-inspiring, beloved mother?,” and beheading his mother’s doppelgänger.
After mentioning his own mother to Riddle, Deuce immediately apologizes, saying, “People told me I shouldn’t bring up parents around you!,” but Riddle credits his mother’s educational regime with getting him into “proper baseline shape as a child” so that he was able to handle a ballet lesson from Rook: “My mother’s tutelage is the reason I can do this now. I’m grateful to her for that.”
When Deuce comments on the Princess in the Tower seeing the witch in her tale as “a kindly mother she could trust” he again apologizes to Riddle, who says, “I told you it doesn’t bother me.”
Twisted Wonderland Reference Note 