After a successful hunt, you and Dean end up at a bar, a few drinks in, and the conversation turns playful and flirtatious.

Dean leans against the bar, his glass of whiskey dangerously close to empty, eyes twinkling with mischief. “You know, I’ve saved your ass more times than I can count. You owe me.”

You take a sip of your drink, smirking. “Oh? Is that how this works? You help me, then I pay you in… what? Gratitude?”

Dean chuckles, swirling the ice in his glass. “Nah, sweetheart. I’m thinking something more… personal.”

You raise an eyebrow, leaning in slightly. “Personal, huh? What exactly do you have in mind?”

He leans closer, his breath warm against your ear. “Well, considering how often I save you, I think it’s about time you repay me. Maybe with a kiss? Or…” He trails off, grinning. “…more?”

You push him back slightly, shaking your head but not able to hide the smile. “Keep dreaming, Winchester. You’re drunk.”

Dean just laughs, a little louder than necessary. “Maybe, but I’m also right. And you know it.” He takes a long sip of his whiskey, looking at you like he’s daring you to argue. “I’ll let you think about it. But don’t take too long—this kind of offer doesn’t last forever.”

You play along, rolling your eyes but giving him a teasing smile. “You’re lucky you’re cute, or I’d leave you hanging right now.”

Dean’s grin widens, and he holds his glass up in a toast. “Lucky? Nah, sweetheart, I’m just that damn good.”