—————- Dean: The first time you had laid eyes on Dean Winchester, wasn't anything you would consider to be special. Actually, you had been with a group of friends, celebrating your best friend's upcoming wedding; and you weren't looking for any interruptions... or a quick hookup. Dean, however, didn't seem to take the hint... not that you minded much. He had been smooth and flirty, typical of any guy who was aiming to get dirty in the backseat of his car. Although, you had also seen something different within the sexy, green-eyed man. He was troubled and lonely, wanting to spend the night with someone who might actually pretend to give a shit about him... and after a few hours of chatting with the older Winchester, you couldn't deny the fact that you were starting to care. "I know that you're here with some friends, [Y/N]..." he had began, flashing you a small smile. "...but do you wanna go somewhere a little less noisy? I think I saw a diner down the street; and I'd really like to talk with you some more."
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Castiel: During your first encounter, Castiel was quiet... almost too quiet. He stood awkwardly to the side, not sure of how to approach you, let alone talk to you. He was obviously nervous, his hands always playing with the sleeves of his trench coat and his teeth tugging at his bottom lip. Normally, you wouldn't have given a man like Castiel, a second glance... actually, you probably would've left the room, thinking that he was just some creep. However, something about the angel intrigued you; though, you couldn't exactly place your finger on what. So... you approached him, holding out your hand in a friendly gesture, while introducing yourself. "I apologize if I made you uncomfortable, [Y/N]." he had told you later that night, his gorgeous blue eyes twinkling. "I was not sure whether I should make advances towards someone so beautiful."
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Sam: Meeting Sam Winchester, had been anything but conventional. Well... unless you believe that a wendingo's cave is a normal meeting place. You had been tied up, watching as the wendingo brutally tortured and murdered the others he had captured. Hadn't his mother taught him, not to play with his food? Nevertheless, you knew that your days were numbered... or at least, they had been until Sam Winchester showed up. Sam had been extremely sweet, quickly untying you and carrying you out of the cave; though, you could have just as easily walked yourself out. He comforted you and explained the situation, doing his best to ease your jumbled mind, before offering to take you into the nearest town for food and a much-needed nap. "[Y/N], I know that everything is really confusing, right now..." he had sympathized, smiling reassuringly when you clutched at his calloused hand. "...but just give it some time. I promise, everything will fall into place."
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