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i. You compliment him in front of everyone.
Unbirthday parties were not unusual for you. Spending almost all your time with Ace and Deuce meant you had an open invitation at all times, and today was no different.
Everything was proper as it could be until Grim sneezed directly into a teacup, causing a minor commotion.
"Ugh, Grim," you groaned, reaching for a napkin.
"Myah! Not my fault somethin' went up my nose!" Grim shot back, waving his tiny paws in indignation.
Ace snickered from next to you. "Real nice, furball. I think Cater got that on camera."
"You wanna say that again, tomato head?" Grim growled, but you held him back.
"Tomato head?" Ace only grinned wider. "What, did you run out of good insults?"
"Can we not start a fight at an unbirthday party?" Deuce said, eyeing Riddle from the corner of his eye.
"What? I'm behaving." Ace said.
Across the table, Riddle cleared his throat. "If you're quite finished with your antics, I'd like to remind you that proper decorum should be maintained at the table. That includes not flinging insults across it." His eyes flickered briefly toward Grim, who had, thankfully, stopped snarling at Ace.
For a moment everything went back to normal again but Ace decided to stir up trouble.
"So," he started, leaning back in his chair with an easy grin, "I've been thinking–"
"Oh, since when did you start to think?" you teased, snickering into the palm of your hand.
Ace ignored your jab, looking around at the others. "Since we're all here, why don't we ask some questions?"
Everyone gave him a look.
"Oh, relax. It's not like I'm gonna break a rule. But I do have a good question. One that everyone has to answer."
The curiosity around the table piqued, conversations pausing. Riddle set his teacup down, looking unamused but willing to hear Ace out. "As long as it's appropriate."
"Totally," Ace said, all in false innocence, before he grinned. "So. Who's the best-looking person in Heartslabyul?"
"Myah, obviously me!" Grim chimed in immediately.
"What–" You shook your head. "Grim, you don't even count! You're a Ramshackle student!"
"Why not? I live in Heartslabyul whenever we visit!"
"That's not how this works!"
"That's totally how it works!"
"Okay, okay, real answers now," Ace turned to Deuce. "Deuce?"
Deuce sighed. "I don't really think about that stuff, but I guess Trey?"
"You just respect him," Ace said.
"That's part of it, yeah."
Riddle shook his head. "This is a completely frivolous discussion."
Ace grinned. "Aw, come on, Housewarden. What's the harm?" Then his gaze flickered to you. "And what about you, Prefect? Who's the best looking in Heartslabyul?"
Now you were the one on the spot.
"Why are you even asking me?" you asked.
"Answer it, Prefect." Ace pressed, his grin widening. "Unless you have something to hide."
You sighed and glanced around, scanning the table. Grim was not an option to begin with. Cater was handsome in the totally Magicam-worthy way as he put it, but so was Trey in that grandmothers-would-also-compliment-him way. Ace had a certain charm if you completely ignored all the stuff that came out his mouth, and Deuce looked endearing, sweet boy and had that ex-delinquent appeal going on if you ignored that he was hot headed and a little dumb.
Your gaze landed on Riddle again. His brows were furrowed, his lips pressed together as if bracing for whatever nonsense was coming next.
You mentally grimaced before saying, "I think it's Riddle."
A silence fell over the table. Everyone paused.
"What?!" Ace asked loudly, unable to hide his surprise.
"Why?" Deuce added.
You leaned on your palm, tilting your head. "Riddle takes care of himself better than most people I know. He's always neat, prim, and... uh, proper—that's the word! Even when things get out of hand, he still manages to look... well, proper. And it's not just the way he looks, he also carries himself with that same energy!"
Another beat of silence stretched across the table.
Riddle's face was red. "Thank you, Prefect," he stammered, straightening in his seat. "But this is hardly an appropriate topic for an Unbirthday Party."
Cater let out a low whistle at that.
"Didn't think you had it in you, Prefect," Ace teased, nudging you. "I was expecting something basic, but that was some real high-class flattery."
"It's the truth."
Riddle cleared his throat sharply. "This conversation is over."
"But not before we get your answer!" Ace pointed out. "C'mon, Housewarden, who's your pick?"
Riddle sent him a glare. "Be quiet, or it's off with your head, Trappola."
"Man, I was just trying to start some drama."
"Keep your mouth shut for once, Ace." you said, kicking him from under the table.
The conversation then moved on, but the warmth on Riddle's face did not.
ii. You fall asleep on his shoulder.
Your head drooped slightly as you struggled to focus on the words before you and the words being told to you. The long day of classes, paired with Grim's endless energy and the usual bouts of trouble Ace and Deuce dragged you in, had drained you completely. You had started this study session with the best of intentions, but the combination of warmth, silence, and exhaustion made your eyelids unbearably heavy.
Riddle was in the middle of explaining something when your head tipped forward, only for you to jerk upright again.
Riddle paused mid-sentence, watching as you blinked sluggishly, clearly losing your battle against sleep. "Prefect," he said, his voice demanding your immediate attention. "Are you even listening?"
"Mmh." You gave a half-hearted nod, though it was obvious you hadn't processed a word. "Something about… cans of tuna?"
Riddle sighed. "I said nothing about tuna. I was explaining–" He stopped himself, watching as you blinked even slower than before. "Perhaps we should take a break."
You made a small sound, too tired to speak. You just needed to rest your eyes for one second, and you'll go back to studying. Just a second and you'd be up again…
Then, before Riddle could say anything else, you slumped sideways, head landing directly on his shoulder.
Riddle went completely rigid.
His grip on his pen tightened. His mind stuttered, words vanishing from his tongue. His first instinct was to tell you off—straighten up, maintain proper posture, do not fall asleep on someone at a study table—but when he glanced down at you, mouth halfway open to scold, he hesitated.
Your breathing was slow. The tension in your shoulders had eased, and without the usual spark of mischief, exasperation or exhaustion in your expression, you looked very peaceful.
Riddle swallowed hard.
This was improper and very undignified. If anyone saw him, it would be terrible.
Now, what was he supposed to do?
Despite various thoughts,he did not move.
Slowly and carefully, he turned his head forward again, his face burning. His hands fidgeted with the edges of his book, but his previous train of thought had been completely derailed.
Your weight against his shoulder was surprisingly light, warmth seeping through the fabric of his uniform. It wasn't unpleasant. If anything, it was… comforting, if he could call it that?
Nobody had slept on him before.
Minutes had passed. Maybe more. He was too flustered to keep track. Finally, when he was certain his face couldn't get any redder, he cleared his throat.
"Prefect," he said, quieter this time. "You should wake up."
You mumbled something incomprehensible, shifting slightly but not moving away.
Riddle exhaled sharply. Gathering every ounce of dignity he had left, he straightened his back further and gently nudged you.
"Wake up," he repeated, firmer now.
You groaned softly before blinking up at him, drowsy and disoriented. "Mm… what happened? What did I miss? Oh, Riddle."
"You fell asleep," Riddle said, trying to keep his voice steady.
Your eyes widened slightly as you realized where your head had been. "Oh… oh! Sorry, I didn't mean to–" You sat up quickly, rubbing your eyes with the back of your hand. "I was just… really tired."
Riddle turned his gaze away, attempting to school his expression into something neutral. "It is fine," he said, though the stiffness in his voice betrayed him. "But next time, do try to stay awake."
"Yeah, I am sorry," you gave him a sheepish smile. "I know you took the time out of your busy schedule just to teach me. It won't happen again, I promise."
"It's…" He exhaled. "It's fine. You should take better care of yourself, Prefect. If you're this exhausted, perhaps you should reconsider how you manage your time."
"You are right…" you trailed off. "I am really sorry, though. I will try to get more sleep."
Riddle hummed, shutting his book close. "That's enough studying for today. We'll continue another time when you're actually capable of retaining information."
"Oh, of course. Thank you," you smiled, picking up your items.
Riddle let out a sigh when you finally walked away.
It took a long time before his heart settled back into its usual rhythm.
iii. You link your arms with him.
Riddle was not particularly fond of crowds. More specifically, he was not fond of being jostled, or people with no regard for personal space, or the chaos that came with large gatherings.
It was the reason why he hesitated when you had invited him to join you on an outing to the town near Night Raven College. At first, he had been inclined to decline but after some insistence (you just asked him politely, twice), he agreed.
And here he was. He found himself almost colliding with someone more than once.
Then, you suddenly looped your hand around his arm and pulled him closer to you.
"Prefect! What do you think you're doing?" he asked.
You blinked at him, tilting your head. "What? I don't want to lose you in the crowd. This way, we won't get separated."
"There's no need for such a thing–" He stopped himself when someone pushed past a little too roughly, nearly knocking into him. Instinctively, he leaned towards you.
"See?" you smiled. "It's practical."
Riddle's face burned. Practical or not, this was not something he was used to.
With a sharp inhale, he turned his head forward, focusing on anything but you. "Very well," he muttered. "But do not pull me around like some child."
"Of course not!" you grinned.
Riddle exhaled slowly, willing the flush on his face to fade. He would simply have to endure this.
iv. You fix his hair for him.
Riddle always looked put together and proper (as you had mentioned in the unbirthday party). Never a wrinkle on his clothes, shoes always cleaned, no strand of hair out of place.
Which was why you immediately caught onto the tuft of red hair sticking out at an odd angle. You eyed his hair while he examined the display of desserts in the bakery. He was completely unaware of the imperfection.
"Hold still for a second," you said suddenly.
Riddle blinked, turning to you.
Before he could say anything, you reached out and smoothed down the strand, brushing your fingers gently through his hair to put it back into place.
His breath hitched, and every thought about pastries evaporated right out of his mind. The warmth of your fingertips barely lasted a second, but it left an undeniable trail of heat on his skin.
You pulled back, inspecting your handiwork with a satisfied smile. "There! All fixed."
"You–" He cleared his throat, forcing his voice to remain steady. "That was unnecessary."
You only shrugged. "It was bothering me."
"Bothering you?" Riddle repeated.
"Yeah. You always look so put-together, so seeing your hair out of place felt… different." You waved a hand vaguely. "And you always like to look presentable, especially in public."
Riddle turned his gaze away, unable to meet your eyes. "You shouldn't be so casual with things like that," he muttered.
"Why not?" You tilted your head. "Friends help each other out, don't they?"
He inhaled, calming down.
"I suppose," he finally conceded, clearing his throat. "We should continue. We have other shops to visit."
"Right," you said, eyeing the desserts, while Riddle found himself absentmindedly touching the spot where your fingers had been.
+1 He takes your hand and kisses it.
It had been a long but pleasant day. The trip to town had gone smoother than expected, despite the crowds and Riddle's initial reservations. He had even managed to enjoy himself although it had more to do with you being there.
Now, as the sun dipped below the horizon, casting the sky in soft shades of pink and gold, you and Riddle stood in the hall of mirrors. The walk back had been peaceful, the quiet between you feeling natural rather than awkward.
"You were surprisingly tolerant today," you teased, nudging him lightly with your elbow. "I thought for sure you'd be upset at people for improper behavior."
"I am not as strict as you make me out to be." Riddle huffed.
You gave him a questioning look.
He sighed. "Fine. I just didn't want to ruin the outing. You seemed to be enjoying yourself."
You blinked at him, caught off guard by the admission. Then, a slow smile spread across your face. "You're sweeter than you let on."
Riddle stiffened slightly then exhaled sharply, shaking his head. "Honestly, Prefect, you have no restraint with your words."
You only grinned. "Agree to disagree."
He gave you an exasperated look before his gaze flickered down for a brief moment. Then, with a sudden movement, he reached out and gently took your hand in his.
You froze, curious about what he would do next.
Before you could react, Riddle lowered his head slightly, pressing a light kiss to the back of your hand.
Your face felt like it was on fire, and for the first time that evening, you were the one flustered. "Riddle?"
He straightened, a small smile on his lips as he released your hand. "Consider it a return for your… gestures today," he said smoothly, though the faint pink on his ears betrayed his composure.
You gawked at him, words completely failing you.
Riddle felt internally delighted at your reaction, clearly pleased with himself for getting you back. "Good day, Prefect," he said, turning towards the mirror to his dorm.
You stood there for a moment, before quickly mumbling a quick 'have a good day'.
Riddle Rosehearts had just turned the tables on you.