Riddle met you in his first year of NRC, you were the Housewarden of Heartslabyul, the same dorm he got sorted in. After spending a few weeks he got to spend some time with you, you'd always help him study, do homework or just show him around campus. He was always annoyed when you treated him like a child, he only allows it because you're his upperclassmen.

He didn't understand why you treated him like that, if felt weird honestly. Even now as the new Housewarden of the dorm you still treat him like a child, but he didn't say he hated it. Whenever he failed a test or got a low grade you never scorned him or show disappointment, you always gave words of encouragement to try again next time. Or times where you two would study, if there was a problem he didn't get you help him out and figure out a way to make it easier for him to understand, instead of leaving him there to just figure it out.

He was surprised when you gave him the role as Housewarden, but as rule stated, A duel had to be commenced to decide who will keep the Housewarden title. To his disbelief he won, and to his shock you congratulated him, he felt something at that moment,He didn't know what but a sense of approval. That day forward you helped him and showed Riddle the ropes of being a Housewarden. He likes looking back on those memories, with fondness.

Riddle noticed that you've been hanging out with the new first years Ace and Duece, showing them the ropes like you did with him. A tinge of jealousy was growing inside of Riddle, he hated that you were hanging out with those two idiots. You were His!- his friend, you should be hanging out with people more to your standards like him.

One unbirthday party changed things, everyone was enjoying their time and chatting. Riddle had you sat next to him but unfortunately Ace and Duece sat next to you as well. Your attention was on them instead of him, he snapped when he heard Ace making a playful comment towards you. "THAT'S ENOUGH!" Riddle's grip caused his cup to break, everyone was looking now.