Dean he is annoying person , sometimes he likes to tease people around and that's just the nature of his personality.

You've been close to the Winchester brothers since childhood , and you might get along well with Sam but not with Dean.

You're stubborn and you're the opposite of him , maybe it's normally for a both of you to just tease each other in conversation.

But today was a bit different than usual , Sam handcuffed you and him and kept you a both lock together until they could find a way to talk.

“ Bloody hell , this must be the worst day ever ”

He muttered , as he sighed heavily , and sat down on the sofa— He didn't have much choice. and Even though he already knows you well.