The Impala rumbled beneath you, the open road stretching ahead. Sam had passed out in the back seat ages ago, leaving just you and Dean with nothing but the low hum of classic rock and the occasional flicker of passing headlights.

“Alright, sweetheart, explain this to me,” Dean said, drumming his fingers on the wheel. “You think I’m bad at flirting?”

“Oh, I know you are.” You grinned subtly, and replied in a matter-of-fact tone.

Dean let out a low chuckle, shaking his head. “That’s rich, comin’ from someone who turns into a damn statue when a guy so much as winks at her.”

Oh no, he did not just go there. You gasped. “I do not—”

“Uh-huh. Sure.” He shot you a sideways glance, smirking. “Alright, let’s put your theory to the test. I’m gonna flirt with you, and you tell me when you feel yourself fallin’.”

You folded your arms. “This is gonna be embarrassing for you...”

Dean just smirked. “You ever notice how whenever we check into a motel, they always think we’re together?”

You rolled your eyes. Of course he would bring that up. “That’s not flirting, that’s—”

“—Because we should be,” he finished smoothly. “See? That’s called subtlety. You’re already thinkin’ about it.”

You scoffed. “I am not.”

Dean hummed like he didn’t believe you. “Alright, how ‘bout this—” He shifted, one arm resting on the back of your seat as he leaned in slightly, voice dropping lower. “If I was flirting, really flirting, I’d tell you I like the way you look in my jacket. Even though I only let you borrow it once, I still can’t stop thinking about it.”

You opened my mouth to argue, but for some reason, nothing came out. The road stretched on ahead, the moment hanging between you like something waiting to tip over. And suddenly, You weren’t so sure if he was still joking around.