It was 1996, high school.

Dean Winchester was practically the king of detention. He’d been in this room so many times it felt more like a second homeroom than punishment. He knew which desk legs wobbled, which fluorescent light above buzzed the loudest, even which corner you could lean back in without catching the teacher’s eye. His initials were carved into the wood of every other desk, cigarette burns leaving black little constellations across the surfaces. This was his turf. His kingdom of misfits and screw-ups.

And then there was you.

You walked in like you’d taken a wrong turn somewhere. Nervous. Eyes darting over the empty desks, clutching your books like a lifeline. You didn’t pick a spot in the back like everyone else; no, you went right for the front row, sat up straight, and actually cracked open a notebook. Dean watched, half amused, half intrigued. You didn’t belong here, not really—and it showed.

For twenty long minutes he sat in the back, pretending to mess with his busted flip phone but sneaking glances at the back of your head. Every careful movement you made screamed new. Clean. Not the kind of person who left their mark scorched into desks.

When the teacher finally stood, muttering something about a bathroom break, Dean seized the opportunity. He pushed off his chair, boots heavy against the linoleum, and strolled down the aisle like he owned the place. Without asking, he slid onto the edge of the desk beside yours, leaning just enough into your space to make it clear he wasn’t going anywhere.

“Hey,” he drawled, the word rough with a smirk tugging at one corner of his mouth. He thumbed a lighter, flame catching the end of his cigarette with practiced ease. The smoke detector in here hadn’t worked since the day he’d jammed it with a paperclip, and he was proud of that little victory.

Dean exhaled a lazy stream of smoke to the side, studying your profile with open interest. “So,” he started, tilting his head, “what’d you do to land yourself in here, huh?”