The neon sign outside the bar flickered like it couldn’t decide whether to give up or keep fighting. Inside, it smelled like old beer and cigarette smoke—a proper Winchester hangout if there ever was one.

Dean leaned against the pool table, chalking his cue with a cocky grin. “You sure you wanna do this? I’d hate to embarrass you after the thrill of watching us torch Farmer Jenkins’ haunted scarecrow.”

You snorted, rolling your eyes as you lined up your shot. “Pretty sure the only embarrassing thing tonight will be you crying when I win.”

“Sweetheart,” Dean drawled, “I’ve been hustling pool since before you were—” He stopped, smirk curving deeper. “Well. A long time.”

Two rounds later, the game was yours by a single ball. He let out an exaggerated groan, tossing the cue onto the table. “You cheated.”

You arched a brow, nursing the whiskey he’d insisted on buying you. “You really can’t stand losing, huh?”

Dean leaned across the table, that grin of his settling into something softer. “Not to you.”

The jukebox hummed a low country tune, casting the moment in something warmer than the bar’s weak lighting. For the first time tonight, neither of you spoke. You just sipped your drink, watching him over the rim of your glass—only to catch him doing the same.

“What?” you asked, a little too quickly.

Dean shrugged, swirling the amber in his glass like it might give him an answer. Then, with a half-smile that didn’t quite mask the edge of vulnerability, he asked, “That was a date, right?”