The Roadhouse always had that familiar hum—the low growl of conversations, clinking glasses, music from the jukebox bleeding through the background, and the occasional roar of a motorcycle outside. You’d been working there with Ellen and Jo for a while now, practically part of the family. Ellen trusted you behind the bar, Jo leaned on you like a sister, and more often than not, you were the one who smoothed out the fights before they started. You weren’t just a pretty face in a tight shirt pouring drinks—you knew hunters, their stories, their pain, and the life that followed them around like a ghost.

Jo often joked that you were her prettier, smarter half, and while you rolled your eyes every time she said it, it was hard not to laugh. The two of you were inseparable. You could handle a shotgun as well as you could handle a rowdy crowd, and your sharp wit had made more than a few grizzled hunters take a step back in surprise.

It was on one of those typical nights, dust and danger hanging in the air like smoke, when Sam and Dean Winchester walked through the doors. Jo noticed them first, nudging you with her elbow and muttering, “Winchesters.” You’d heard stories, mostly about their dad, but these boys carried their own weight—especially the older one. Dean. He had this cocky smirk that only seemed half-serious, but his eyes told a different story. Sharp. Guarded. And when they landed on you for the first time, something flickered behind them.

He checked you out, sure. Dean Winchester was a flirt by nature, and you knew exactly the kind of attention you were getting. But it didn’t feel like the usual once-over. He looked longer than most did, like he was trying to figure you out—what a girl like you was doing in a place like this, behind a bar slinging beers for battered, blood-stained men. And the moment your eyes locked with his across the room, something unspoken passed between you—some strange, electric knowing.

He didn’t approach right away. Dean wasn’t stupid. He took his time, threw a few jokes around with Jo, got the lay of the land. But his gaze kept flicking back to you, and when the crowd began to thin just a little, he finally made his move. He leaned against the edge of the bar, all leather and charm, and with that grin that made girls lose reason, he spoke up—only to you.

"Hey... could you bring over two beers? One for me, and one for you. I figured maybe you could take a break for a few minutes. Sit with me. I promise I don’t bite. Much."

He chuckled lightly, tapping his fingers against the wood of the bar before glancing over his shoulder at the empty booth in the corner.

"Figured we could talk, just you and me. You work here, you probably hear all kinds of stories… but I get the feeling there’s more to you than just that pretty face and quick hands behind the bar."

His eyes softened for a second, his voice dipping just enough to betray his curiosity.

"You don’t look like someone who ended up here by accident. Jo talks like you’ve got more guts than half the hunters that come through this place. And, well… I like people with guts. Especially the gorgeous kind."

Dean flashed that boyish smile again, but there was a hint of sincerity behind it—like he wasn’t just throwing lines for the fun of it.

"So, what do you say? Ten minutes of your time, a cold beer, and maybe… maybe you tell me how someone like you ended up being the most interesting part of this bar."

He leaned in a little closer, voice low.

"Come on, sweetheart. You’re not gonna make me drink alone, are you?"