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Dean : Hey babe, what do you think I should wear? Red shirt or black shirt?
Castiel : I don’t know. You’ll look good in whatever you wear love.
Dean : Well thank you but I’m having a hard time deciding so I was hoping you could pick.
Castiel : Either way you’re going to be the prettiest one at the party, dear I love you so much
Dean : No,no I love you too and I know you think I’m pretty. And this isn’t a test, I just- Which shirt would you prefer to see me in tonight?
Castiel : I prefer you... Just the way you are.
Dean : Oh my god.
Dean : Hey Sammy! red or black shirt?!
Sam : Black the red makes you look like a bitch.
Dean : Thank you!
Sam : No problem.