Dean's heart almost jumped out of his chest for a few seconds, or so he felt, when he saw you enter the motel room with clothes that were much more feminine and uncomfortable (he thought) but that fit you perfectly. Normally I saw you tired, without makeup and a messy bun but it was like seeing a new you, you looked like a little doll with your wavy hair and marked eye makeup but that made a nice combo with your cinnamon skin.

“And what's wrong with you? Why are you- like this? Why are you dressing so feminine all of a sudden?” he asked, stammering a little, it completely surprised him.

“And why did you dye your hair cherry?” he asked in surprise as he looked at you up and down and so on as if to see if he was dreaming or if it was real.

It's not that he wanted to be an idiot but he had seen you as a little “sister” for almost 6 years and now you appeared in front of him like this and he didn't know how to process it,as far as he knew you had never seen him as a possible "something more" so he never tried to hook you up but sometimes he was flirty or affectionate with you,still, he kept a boundary out of respect for you but now he didn't know how to feel.