Sam
When Sam flirts with you, he tries to be subtle about it, not making it too obvious that he's into you. He jokes around with you a lot, only to make you laugh, lightening up the room with your smile. He enjoys teasing you the most. He likes to hold things over his head, out of your reach so you have to beg through your outbursts of laughter. He tries to keep a serious look on his face, but he can't help but smile at your laughter. He catches himself looking at you for longer periods of time, or at least until you catch him. You know there is something more going on between the two of you, but both of you are too scared to pursue it any further.
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Dean
When Dean flirts with you, which is often, he is upfront about it. He greats you with a compliment on your appearance or pet name he has taken a liking to. Dean is a master at flirting, but you make him more nervous than he has ever been around a girl. You're different, and deserve so much better than his usual bar routine. He starts off with horrible pick up lines that are just bad enough to get you to laugh. Next, he tries his hardest to make it feel like you're the only girl in the room, especially when you're out in public together. He ignores the advances of other women, his eyes never leaving you. His touches linger a little longer, you catching him looking at you when you eat together at a diner, and it feels like the most natural thing. He wants to make you feel beautiful. You soon realize that his flirting isn't just some game, that there is something more going on between you, something that you're definitely willing to act on.
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Cas
When Cas flirts with you, subtly is not his style. He has observed people flirting with each other for a really long time, and he figures it can't be that hard if humans can do it. He starts with a pick up line he heard some guy at a bar use on the bartender the other day, thinking his advances could possibly help you realize that he's into you. He gets a little worried when you laugh at it, asking him where he learned such a horrible pick up line. He then researches what to do next. When he realizes what to do, it comes almost naturally to him. You catch him looking at you from time to time, the gaze on his expression making you blush. He offers to help you with little tasks that you would much rather forget about. His body brushing over yours as you move around the room together. You can't help but wonder what's in store for the both of you, the chemistry becoming undeniable to you. You look forward to what's to come.