Chapter Text
Dates were, quite obviously, not Riddle's strong suit. Frankly, Riddle doesn't recount ever having gone on a date in his entire life. If he doesn't count the “dates” he and his mother had, which were mostly just the two of them spending time together. Aside from those, Riddle had no idea how dates were supposed to go, and true to his nature, Riddle was especially nervous for this one. He wanted it to go well, he wanted to make a good first date and hopefully have a second one if all things went well. (Not to sound excited or anything, Riddle definitely wasn't anticipating this date!)
When he told Cater about his date, the senior all but gasped. Gasped! In his face!
After scolding Cater for his more or less inappropriate reaction, Cater was more than happy to give him pointers and assistance in preparing for his date.
Who was his date? Ruggie Bucchi.
They were definitely an unexpected pair. Riddle, enforcer and strict follower of rules, and Ruggie, infamous for bending the rules to achieve his goals. They don't exactly sound like the most functional of duos.
Riddle even found asking Ruggie out quite odd. It was quite obvious, even at the time, that Ruggie never expected Riddle to ask him out of all people. In his defense, Riddle never thought he would either.
(And he probably wouldn't, if it weren't for some annoying first years and a too-involved third year.)
Anyway, Riddle fidgets with his fingers. Ruggie is, positively late. Riddle starts having second thoughts, perhaps Ruggie got sick? Perhaps he simply decided to not go? Either way, it was making Riddle anxious, and a little irritated. Riddle was always tardy, he was always on time, and he valued being on time quite a lot. So being late, to a first date, nonetheless, was quite inappropriate behavior.
“Heya, Riddle.” Finally, finally, after around 6 minutes and 32 seconds of waiting, Ruggie had arrived. Riddle felt his eye twitch at that casual greeting. Heya? HEYA?! After being 6 minutes late to a first date?!
“Ah, Ruggie.” Riddle tried to keep his composure, he wasn't about to lecture his date. “Did something happen for you to arrive so late? That's not very appropriate for a date.” Riddle tried to stay as calm as he could.
Ruggie wasn't entirely indifferent to his remark, but he was kind of awkward with answering Riddle's inquiries. “I got caught up in some first year business, somethin’ about a missing magical pen.”
Riddle was about to ask more questions, but he decided to just give up. If he knew Ruggie, which he didn't actually, he knew Ruggie wasn't entirely above deceiving others. Call him wrong for doubting his date, but could you blame him?!
Brushing that potential lie off. He simply exhaled and nodded for Ruggie to sit opposite from him, which Ruggie did.
Now comes the difficult part. Riddle didn't know what to talk about, but he didn't want to sit in awkward silence either. “So…” “So.”
Okay, Riddle was unqualified for this. Sometimes he wondered just how Cater could be such a natural conversationalist when it came to these things.
“How are your test results…?” Okay, maybe talking about academics on a date wasn't exactly the best topic, but Riddle was out of options! “Eh. They were alright. Nothin’ to extraordinary, like yours or Azul's, but they ain’t failing either.” Ruggie shrugged. At Ruggie's calmness, Riddle felt a bit more relaxed. Only a bit, though.
“I see. I do believe you could excel if you studied harder.” Before Riddle continued, he was interrupted by a sound.
“Oh.” Ruggie felt a little embarrassed. And Riddle… well, Riddle was Riddle. He quickly got the hint and called over a waiter.
As they began to order, Riddle noticed how Ruggie chose the cheapest meals on the menu. Despite being quite “dense” as Cater would put it (He was not!) Riddle caught on quite quickly. The cheapest item on the menu was nothing more than a glass of juice. That was it. Just a glass of juice.
Riddle felt puzzled. Ruggie sounded hungry, yet he chose… Just juice? While mulling it over, he made a realization. Mentally facepalming for not realizing it sooner.
“Two slices of strawberry tarts and…” Riddle scanned the menu, his eyes lighting up for a moment. “Some donuts, please. Strawberry, if you have any.” The waiter nodded before rushing back to put in their order.
“Really? You didn't have to do that…” Ruggie tried to act nonchalant about it, but he was quite sheepish at the moment. Riddle found it… strangely cute? Like a wet puppy in the rain. For a moment, Riddle found himself comparing Ruggie to one of the hedgehogs back at Heartslabyul.
“It was nothing. It's only customary to pay for your date’s meal, isn't it?” Despite it coming off as a rhetorical question, it was partially genuine because Riddle had no idea how dates actually went and what the customs were. He just didn't want Ruggie to go hungry.
“I guess so. You're not so bad at this, Rosey.” That comment. That singular comment had managed to make Riddle flush with embarrassment. “W-well! I give you my thanks…” Truly, his embarrassment must've entertained Ruggie somehow as the other let out a laugh. It was hardly one of the most pleasing laughs Riddle had heard, but for some strange reason, Riddle thinks Ruggie's laugh might be his favorite. Maybe being embarrassed wouldn't be so bad if he got to hear it again.
“You look really cute.” Ruggie pointed out. “Especially when you're all red and embarrassed like that.” Riddle huffed, trying to keep up his cool facade. “I suggest you be careful unless you'd like to lose your head.” Ruggie only laughed a bit more.
Their conversations flowed freely despite their awkward start. Riddle was surprised to find that Ruggie was actually quite enjoyable when it came to conversations and the date wasn't going as bad as Riddle thought it'd go.
Sure, Ruggie might've taken a joy in teasing Riddle endlessly, but Riddle surprisingly didn't mind. This date was going well.
Really well.
Almost too well.
Riddle found himself almost at awe at how easy it was to have a conversation with the hyena. He can't remember the last time he's laughed as much as he did.
“You've got a real cute laugh, Rosey!” Ruggie huffed out. Riddle found himself stopping mid chuckle, another embarrassed flush creeping up his face. Had he been laughing too much? How unbecoming!
“My apologies…” Riddle covered his mouth with his hand. Ruggie only laughed a little more in return.
‘You’ve got a real cute laugh!’ The words kept playing over and over in Riddle's head. Despite his embarrassment, if Ruggie liked his laugh, then maybe it wasn't so bad.
After their date at the café, Riddle offered to walk a little with Ruggie. Despite putting it as “wanting to make sure Ruggie's time with him was worth it,” he actually just wanted an excuse to spend more time with the hyena. Never would Riddle in his life ever though he'd use an excuse to spend more time with someone, never.
They took a stroll around a nearby park, admiring the abundance of roses and stopping by some vendors and purchasing random things. The whole time, Riddle was focused on Ruggie and Ruggie alone. It was… nice. Riddle never thought anyone could capture his attention so much, but he supposed that there was a first for everything.
Some part of their walk, Riddle didn't notice when exactly, Ruggie's hand had found itself interlocked with Riddle's. He doesn't know who initiated it, but it became difficult to ignore upon realization. He fretted in his mind, wondering if his hands were too sweaty or something of that sort…!
Poor Riddle, he couldn't stop himself from his inner turmoil as they walked rounds in the park. Ruggie noticed and asked him if anything was wrong, Riddle simply shook it off.
After a few minutes of panic, Riddle let himself feel.
Ruggie's hands were rather calloused, possibly from the work he's had to do at a young age, and scarred. Despite them being a contrast to Riddle's own, he found comfort in holding them.
“Your hands feel quite nice.” Riddle blurted out randomly, causing the hyena beside him to blush, if only a little, and quickly mutter a thanks.
As they walked, they both got a bit tired. The sun was beginning to set as they found a nice bench to sit on. Riddle had already calmed himself, and he was enjoying his time with Ruggie thus far.
“So… How has the date been for you?” Riddle asked in a desperate attempt at conversation. “S’been good.” Riddle let out a sigh of relief. “I'm glad. I'm not exactly the most experienced when it comes to dates…” Ruggie only snorted at Riddle's misery.
“I do hope my struggles are entertaining to you.” Riddle retorted, secretly enjoying their banter. “Oh, it's plenty entertaining, rosey! You're a real riot!” They both laughed as they continued on.
“Ah, the sun is setting. I rarely ever saw the sunset as a child.” Riddle pointed out. Ruggie raised an eyebrow. “Right, since ya couldn't exactly go outside much as a kid.” Ruggie nods in agreement. Riddle was aware that pretty much everyone in the school knew at least a little bit of his past since his overblot, but hearing it from someone else was… Well, not exactly comforting.
“When I was a kid, I was out a bunch!” Ruggie shrugged. Riddle tilted his head, curious. “Really? What did you do?” There was a brief pause as Ruggle somewhat panicked a little. “Just workin’ some odd jobs, y'know? Stuff like that! It's been a while, I can't exactly remember all of it.” Riddle, dense but knowledgeable as he was, knew that it wasn't the entire story, but he didn't push.
There was a pause. The air was stiff with tension as the two looked at each other without exchanging words. “That's quite admirable. Working hard at such a young age to provide for your family.” Riddle finally says, and he means it. Ruggie seemed to be happy with that reply, and they both turned their gazes back to the sunset.
“How would you rate this date outta ten?” Ruggie snickered. Riddle sighed in reply, but he indulged.
“Well, aside from you being late and teasing me endlessly, it is…” Riddle thought his words over, before continuing with a fond smile on his face. “It was enjoyable. Very much so… Possibly a seven.”
“Dang, just a seven? I have to amp it up to a ten next time!” Ruggie snorted. Despite it being painted in a joking light, Riddle could faintly make out the hint of genuineness behind Ruggie's joke. (Part of him wishes it wasn't just a joke.)
Riddle pretends he doesn't hear it. Pretends he doesn't anticipate the idea of a next date. He pretends that it doesn't get him all fidgety and giddy about spending more time with the hyena.
But he can't pretend to not feel the way his heart flutters excitedly at the thought of going on another date with Ruggie Bucchi.