Imagine playing a game of 20 questions with Dean in a bar where he shamelessly flirts with you with cheesy pick up lines, trying to tell you how he feels.
“Hey there, stranger.” green eyes sparkled in a way that could make your heart skip a beat but despite the amount of drinks he’d had, it wasn’t that he was drunk. There was something behind those words so you went along with it.
“Hello to you too, stranger.” you placed your beer down on the table and narrowed your eyes playfully at him “You got me surprised, here. There are plenty of beautiful women around and you come here?”
“Don’t know what you’re talking about, I only have eyes for you.” he gave you a casual shrug “Besides, I found out a couple things that-” he bit his lip, looking down at his glass “Gave me the push I needed. So-” he looked back up at you with a full grin “Here I am.”
“Here you are indeed.” you smiled back, pausing to try and understand the flirty yet so relaxed smile on his face “Am I allowed to know what those are or…?”
“In due time. As of now though-” he cleared his throat and for the slightest of minutes you noticed him get nervous “I want to spend the rest of the night with you. In whatever shape or form.”
“Do you now?” you chuckled “Feeling a bit bold tonight too?”
“You could say.” he shrugged, giving you a boyish grin “So-” he cleared his throat, leaning forward on his elbows “I heard you like bad boys?”
You almost choked on your beer, but at the same time couldn’t fight off your – albeit perplexed – smile as you raised an eyebrow “No, no I actually don’t.”
“Oh, phew, thank Chuck.” he actually seemed to relax in his chair.
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So cheesy, SO damn cheesy Winchester!😂 but damn, he’s awfully adorable.

























