Ever since you showed up to Twisted Wonderland, Riddle has never felt more complete.
You started off as associates; walking you to class, helping you understand the basics of whatever questions you had, or offering you to spend time with him in Heartslabyul. He'll sit with you, drink tea or eat pastries.
He always thought you were beautiful; everything you saw as an insecurity he saw as pure perfection: your freckles, your scars, your stretch marks, your imperfect teeth.. no matter how many timed you attempted to hide your smile or laugh behind your hand, he always shooed it away and murmured: 'don't hide. you're so beautiful'.
Riddle was, ultimately, a sweet guy. He always cared for you and those around him; especially on days where you felt depressed. He'd spend hours after hours sitting with you, brushing out your hair and offering to do matching rose-scented skin care masks.
"I'll do those assignments the professor assigned as homework for you," Riddle murmured sweetly as he offered you a cup of tea. The two of you sat in your dorm, quietly tidying up or just chatting about the day. He helped you sit back, propping your feet up with a pillow.
"You just sit there and be pretty, my dear. I'll take away your stress for you."