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“I can’t believe it.”
Riddle huffed as Leona laughed, “I hardly understand why this is funny.”
“You’re the most ass-kissing teacher’s pet in this school, and you’re asking me if you have a chance with Ruggie. A self-proclaimed street rat that doesn’t give a shit about the law much less rules. What isn’t funny about that?” Leona is, decidedly, a dick.
Riddle’s expression turned from irritated to something near crestfallen and pitiful, “If the answered no you can just say that.”
Leona stopped laughing at that and registered just how serious the boy seemed, “That’s- You’re honestly interested in Ruggie?”
“Yes. That’s why I went to you, to see if you would be able to give me advice, but clearly that’s useless since I’m so hopeless.” Riddle’s voice was snippy and he turned to walk away from Leona.
“Woah- hey- Rosehearts!” Leona called out, feeling a little bit bad about the boy.
Riddle froze in his steps and turned silently.
“I didn’t say you were hopeless… he likes donuts, there’s some new bakery in town off campus that he’s been mentioning wanting to go to… if you invite him you might be able to secure a date… just…” Leona’s tail flicked as he didn’t feel comfortable giving assistance or comfort, “Loosen up.”
Riddle’s face seemed to light up slightly in hope, and Leona internally groaned, he was no good at emotions but the boy looked like an excited cub.
“Do you think I actually have a chance?” Riddle asked carefully, but his eyes had these tiny lights in them giving away his feelings.
“A chance, sure." Leona mumbled.
Riddle smiled a bit, “Thank you, Leona-San.”
Leona grunted and turned to go back to sleep.
~~
“Ruggie, I’d like to speak with you, if you wouldn’t mind.”
Leona’s eyes opened to see Riddle standing a few feet away from where he was laying, Ruggie sitting next to him as he worked on some history essay.
“Huh? Yeah- sure, Rosehearts, what’s up?”
Riddle glanced at Leona who hummed a bit, “Go outside if you’re gonna talk.”
Riddle nodded a bit, “I’ll wait at the tree by the exit outside then.” He promptly left and Ruggie started putting his things together.
“Ruggie.” Leona spoke roughly as the hyena stood.
“Yeah?” The boy looked down at the tired lion while the lion studied him.
Ruggie wasn’t someone who easily trusted people, he was willingly manipulative if it gave him an upper hand, and he would go along with other peoples whims even if he didn’t necessarily like the person if he thought it would end with him better in the long run. That being said, he had endured a large amount of mockery and taunting since he was a child, and didn’t really take people’s kind words at face value, that’s why he and Leona went together so well. Leona was rough in the same way that Ruggie was, both of them had earned the others trust to the point that both were brutally aware of the intent and purposes behind each other’s words.
Leona didn’t dislike Rosehearts, he was a good kid, a bit annoying with his rules, but he didn’t have ill intent. He figured he might do the kid a favor, “Rosehearts ain’t one for petty schemes, he means what he says. Be… nice if you say no.”
Ruggie made a face, “‘Scuse me?”
“Just go, I’m going back to sleep.” Leona grunted, but as his eyes closed, his ears stayed alert to the footsteps of his underclassman.
~~
“What’s it you needed to talk to me about, Rosehearts?” Ruggie tilted his head as he approached and one of his ears flicked a bit.
“Ah… there’s a bakery I heard you wanted to visit…” Riddle shifted a bit.
“Oh- uh, Yeah, what about it?” Ruggie made a face.
“I’m… if you’re willing… or if you’d have me, rather, I’d like to accompany you… or, take you there… at some point…” Riddle’s face had turned red in the way it often does when he was angry or upset and Ruggie made a face.
“You… What?”
Riddle grew more red and Ruggie was honestly somewhat worried before Leona’s words clicked in his head. Oh.
Oh.
Riddle was asking him on a date.
Riddle wanted to ask Ruggie out and Leona had advocated for him of all people.
Ruggie didn’t know what to say honestly, Riddle was attractive, there was no need for him to deny that, but he hadn’t spent much time ever thinking about romance with other people. Riddle especially was not really someone Ruggie would think of as an ideal partner, just because the boy didn’t seem to be someone who’d be able to handle Ruggie’s personality.
Then again here was the boy asking him out on a date.
Was Riddle someone Ruggie could see himself dating? Maybe?
Ruggie looked into Riddle’s eyes and instinctually searched for insincerity, like Leona had said, all he found was hope and an overwhelming amount of fear.
Riddle opened his mouth to speak but Ruggie spoke first.
“Sure.”
“It’s- What…?” Riddle looked up and the hope in his expression grew.
“I can’t guarantee that you’ll want to go anywhere with me again afterwards but… sure, You can take me to the bakery one day, we’ll see how it goes from there.” Ruggie spoke awkwardly.
Riddle smiled and he nodded, “Right… I should be free Saturday morning… or Monday afternoon if you have Magift practice then.”
Ruggie shook his head, “No practice Saturday, that works fine, pick me up at my dorm.”
Riddle nodded slowly, “I’ll do so, I’ll… see you then, I suppose.”
Ruggie nodded, “See you then… Riddle.”
Riddle smiled brightly and nodded before he left.
~~
Riddle yelled into a pillow as he fell onto Cater’s bed next to the boy who was sitting on his phone.
“Is that a good yell or a bad yell?” Cater looked down at the second year.
Riddle pulled his head up and he revealed a blinding smile to Cater who smiled back.
“He agreed.”
“He did?”
Riddle nodded and Cater smiled more, moving to lay on his side to face Riddle more properly, “Tell me more.”
“He seemed a bit confused at first and I was honestly about to back out but then he said sure, and-“ Riddle’s face was pink in a flustered way rather than upset, “He said he wasn’t going to guarantee anything after that but he agreed and we’re going on Saturday.”
Cater smiled for him, “Well, I guess that means I’ll have to take you shopping for an outfit for Saturday then, make sure to guarantee a second date.” He teased softly.
Riddle looked alarmed, “Do I need to dress a certain way?”
Cater laughed, “Nah, don’t worry, Ruggie ain’t someone who cares about that, I can still take ya if you want though.”
Riddle thought a bit before nodding gently, Cater hummed and the two fell into conversation. Cater smiled when Riddle finally left the room, he had never seen Riddle act so much like an actual teen before, he was glad the housewarden had learned to at least somewhat live in the moment.