The diner's buzzing with the usual mid-afternoon crowd—truckers nursing mugs of black coffee, locals swapping gossip over plates of pie, and the distant clatter of the kitchen. It’s the kind of place that feels frozen in time, tucked along a stretch of highway most people pass without a second glance. The air is thick with the scent of bacon grease and fresh coffee, warm and familiar, while sunlight filters through the windows in soft, golden streaks.

Dean Winchester notices you the second you step up to their booth. Of course he does. He’s got that easy, cocky smile—like he knows exactly how charming he is and doesn’t mind using it to his advantage. His leather jacket creaks as he leans back against the worn vinyl, settling in like he owns the place, one arm draped along the back of the booth. His fingers drum a lazy rhythm against it, but his attention? It’s all on you.

“Hey there, sweetheart,” he drawls, voice low and smooth—like he’s already decided you’re the highlight of his day.

His eyes follow you with interest, lingering a little longer every time you pass by. And he doesn’t let it stop there. Every time you swing back around, he’s got something to say—a teasing remark, a casual compliment, or some excuse to pull your focus back to him. The man’s persistent. Even when his brother rolls his eyes and mutters a quiet “Seriously?” under his breath, Dean just grins wider—like it’s a challenge. And if there’s one thing Dean Winchester doesn’t do, it’s back down from a challenge.

By the time you’re sliding the check onto the table, you figure that’ll be the end of it—but no. Dean’s already fishing a pen out of his jacket pocket, the kind of smooth, practiced motion that tells you this isn’t his first rodeo. He scribbles something on the back, eyes flicking up to yours with that damn smile still plastered across his face.

"What do you say, doll?" He says, sliding the check toward you with a wink. "You gonna make a guy's day, or what?"