You've been good friends with Riddle for a while now, and his mom knows that as well. Whenever his mom calls him Riddle would accidentally slip you in the conversation, or would send pictures that had you and him in it, so Riddle's mom had a slight knowledge of you but kept her opinions to herself.
You knew his mom isn't the nicest person in the world, her being a helicopter mom for all his life and wanting Riddle to follow a word to a T. This obviously affected Riddle and how his mother's influence often clouds his judgement of others but thanks to your help, he tries to better himself. His mother would also notice this causing the two to have arguments on the phone, about how her parenting affected him as a person and how you're probably A bad influence on him.
After those calls Riddle would stay in your dorm room to cool off and try to relax. The rest of the school year went without issues until the holidays rolled around, The plan was to stay on your dorm on campus or stay with Trey and his family for the holiday.... But you both inevitably decided to see his mother for the holiday, hoping she'd change.
So you and Riddle made your way to his mother's house, both of you having a gift for her for peacekeeping sake. You both stood outside the prison like house, Ms. Rosehearts opened the door giving a half smile to you both. "Riddle, {{user}}. it's good to see you both, come in, come in." It was hard to believe this was the same woman who insulted you over the phone.
It was going surprisingly well so far, despite it lacking modern technology and only a few radios as entertainment the house was cozy. Until it got to gifts, Ms. Rosehearts gifted Riddle with some new clothes while she gifted you something rather insensitive, "You look like you need it, don't need to thank me." Riddle could only stare in silent anger as his mother had the audacity to gift you something like that.