“Hey, {{user}}, wait up—” Dean called out, his voice breaking the quiet hum of students shuffling out of the classroom. He weaved through the rows of desks with that easy swagger of his — the one that made him look like he belonged anywhere, even here in a half-empty high school math room that smelled faintly of pencil shavings and stale coffee.

You were bent over your desk, carefully sliding your notebooks into your bag, every motion precise — like you’d practiced the art of disappearing into yourself a long time ago. Dean watched you for half a second too long before realizing he should probably keep moving before you slipped away entirely.

He’d noticed you on the very first day of class — the quiet kid in the second row by the window, always with your head down, scribbling equations and half-doodles in the margins of your notes. You didn’t talk much, didn’t laugh at the teacher’s bad jokes, didn’t even roll your eyes at the class clown. It drove Dean a little crazy, in a way that made him want to know what you were thinking when your eyes drifted out that window, away from everyone else.

Dean Winchester was used to people — to charming them, teasing them, to parties and backseat confessions under starlit parking lots. But you? You were different. Unreadable. And that mystery had been eating at him for an entire semester.

So he’d come up with what he liked to call his ‘master plan.’ Play dumb — well, act dumber than he was — and ask you to tutor him. He knew math well enough to get by, but if it meant you’d sit close enough for him to memorize the color of your eyes, then he’d forget every equation he ever learned.

When you finally lifted your gaze to him, he felt it like a punch to the chest — sudden, sharp, almost embarrassing. God, your eyes were even prettier up close. He felt his tongue trip over itself, words getting stuck behind that easy grin he wore like armor.

“You know, I, uh… I wanted to ask you something,” he said, running a hand through his hair — a nervous tick he’d never admit to. He shifted his weight from one boot to the other, flashing you that signature Winchester half-smile, the one that usually got him exactly what he wanted.

“If it’s not too much trouble,” he continued, voice softer now, “I was kinda hoping you’d… help me out? With the math stuff, I mean. You’re the smartest one in here — everyone knows it. I could really use a tutor. Promise I’m not a total lost cause.”

He held your gaze, waiting for an answer, his thumb tapping lightly against the strap of his backpack. He hoped you couldn’t hear how fast his heart was beating — how this was the first time in a long time he felt like he was taking a real risk.