The Academy's Terminally Ill Side Character
Chapter 129: It’s Not A Date [1]

Chapter 129: It’s Not A Date [1]

"Hey Leon, tomorrow’s Saturday."

"Yeah? And?"

"It’s also a holiday."

"...Okay?"

"So... are you free tomorrow?"

That was the moment Leona—yes, the crossdresser—who had been casually scrolling through reels on her phone, glanced up and blinked at me like I just short-circuited her brain.

To be fair, it was a bit sudden. I had just come back to my apartment after overhearing a conversation between Leo and the others, and now I was standing here asking Leona out.

Well—not like that. It wasn’t a date or anything.

See, the academy had rewarded me a decent chunk of achievement points after the recent... chaos. Enough to finally spend on something useful. Potions, gear, maybe some enchanted items—anything that could help me not die the next time someone went nuts.

But there was one small issue.

Okay. Maybe not small.

I didn’t know how to buy things here.

Laugh all you want—it sounds dumb, I know. But this world’s shopping system wasn’t as simple as swiping a card or tapping an app. The academy’s marketplace was all integrated into a weird blend of magic and tech, tied to one’s mana signature, spatial inventory, academy permissions... and a bunch of other stuff I only read about in the novel.

Reading about it was one thing. Using it myself? A whole different beast.

So yeah, I needed help.

And while I had a few options, none of them were exactly ideal.

Ryen was the most reliable choice. He’d definitely lend a hand, but he went back to his hometown during the holidays. I didn’t want to bother him while he was spending time with his family.

Leo? Absolutely not. That guy would either act like he knew everything and get us hopelessly lost, or he’d drag me into side-quests that involved haggling over socks or arguing with a shopkeeper about muscle balm.

Then there was Nora Hayes. The yandere. The girl who was unhealthily obsessed with Ryen. Asking her for help would be like lighting a fuse next to a powder keg. If she misinterpreted even one word of what I said, I might not survive to see tomorrow’s breakfast.

Professor Lena also crossed my mind. She was knowledgeable and probably knew this system inside-out. But let’s be real—if I was seen strolling through the shopping district with a beautiful 26-year-old single professor, half the academy would start calling it a "weekend date," and the other half would start whispering rumors that I was seducing faculty for good grades. And given my current "young master who bullies his butler" reputation, I really didn’t need that extra fire.

Which brought me to Leona.

Yes, Leona—the young lady from a noble household who was pretending to be a guy, attending the academy undercover, and hunting for a potential husband without outing herself. Not exactly a normal profile. But out of all my options... she was the least likely to misunderstand my intentions or get me killed.

And so, after weighing my choices carefully and accepting my fate, I made the decision.

That was why I was now standing awkwardly in front of Leona, clearing my throat and trying to sound casual.

Leona blinked once. Then twice. Then she tilted her head, a suspiciously slow smirk tugging at the corner of her lips.

"...Wait. Are you asking me out on a date?"

I nearly choked. "No! I mean—yes? Wait. No! Not that kind of date!"

Leona arched a perfectly sculpted brow. "Mmhm. So you’re not asking me to spend an entire holiday walking around with you, helping you buy things, giving you fashion tips, and maybe stopping for lunch at a cozy little cafe?"

"That’s—! That’s just shopping with benefits!"

"Wow." She let out a low whistle. "Rin, didn’t think you were that bold."

"I’m not being bold, I’m being desperate!"

That got a laugh out of her. Not a mocking one, though—more amused than anything. She tossed her phone onto the bed behind her and leaned back, hands behind her head.

"Well, desperate or not, you’re lucky. I am free tomorrow. And I’m curious to see how badly you fumble your way through our magic-commerce hellscape."

I let out a breath of relief. "So that’s a yes?"

"It’s a yes, loser." She grinned. "But it’s not a date."

"Of course it’s not, why would I go on date with a ’BOY?’ I’m interested in girls."

At the words of boy, Leona felterd for moment and remember her role, yes, at the moment she was pretending to be boy and no one is know about this.

Including her roommate, Rin Evans.

But to bad for her, I know all about it since I read the novel.

She was messing up with me now and now she isn’t saying anything when I used the word ’BOY’.

Heheh, that’s what you get for trying to make a fun of me Leona.

Leona looked at me and narrowed her eyes, clearly trying to figure out whether I was just being dense or if I knew.

She held the stare for a second longer than necessary.

"...Boy, huh?" she said slowly.

I shrugged, trying my best to keep my expression neutral. "What? You are one, aren’t you?"

"Of course." Her smile was calm... too calm. "Totally. One hundred percent. Very boy."

I nodded seriously. "Super masculine. Bro energy. Beard-growing potential."

That earned a quiet snort. "You’re pushing your luck, Evans."

"Am I? I’m just being supportive of your manliness."

Leona leaned forward, eyes gleaming. "You know, you’ve gotten kind of bold lately. Did someone feed you confidence pills, or are you just planning to die tomorrow and figured you’ve got nothing to lose?"

"Neither," I replied casually. "I just figured if I’m going shopping in hell, I may as well enjoy the flames."

Her lips curled into a smirk again, amused but thoughtful. She tilted her head and stared at me like someone trying to see through frosted glass—half guessing, half measuring.

"...You’re weird, Rin."

I gave her a mock bow. "Thank you, I try."

She shook her head, chuckling, then stretched with a yawn and waved her hand lazily. "Alright, loser. Meet me by the south gate at ten tomorrow. And don’t be late. If I have to wait more than five minutes, I’m charging you extra for emotional damage."

"Got it," I said, giving her a mock salute. "I’ll even bring a coupon."

Leona rolled her eyes, but the small grin on her face didn’t fade.

As I turned to leave, I caught a glimpse of her in the mirror—watching me, the way someone might watch a puzzle that’s almost figured out but not quite there yet.

She was suspicious.

But not sure.

And that was enough to keep things interesting.

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