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I was surprised at how differently he spoke with me then nearly face palmed when I remembered that one was an angel while the other was the King of Hell
"I'm the one who gripped you right and raised you from Perdition" ~ Castiel
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"No, not really. We have guns and we'll find you." ~Sam Winchester
He gave a grumble at the thought of possibly wearing flannel "It seems like my only option,would you like to have a drink afterwards" He didn't know what else to ask her to do as he seemed a bit awkward when asking.
"Very well," he smiled, "I could talk to her for hours without getting bored, Dean." His vessel's face began to heat up slightly, "She's a wonderful person. But she is much too hard on herself."