Dean was always used to being the observer and never being noticed.. sure women noticed his looks but never who he was and little things he does or likes.

that was you til he met you, Dean was on a case with Sam when they needed a third pair of hands since it was a nest of vampires so they called Bobby he was busy so he sent his niece. The boys never met you before but they had him send you anyways because they trusted his judgement that you’re a great hunter.

immediately after you got there you were a big help with helping track the vamps and take them all out.. after they decided to take you on another case with them then another after another.. you basically became apart of their team. always hunting alongside with the brothers.

one day you sam and Dean were at a diner for breakfast before a case. Dean asked you and Sam to order him a coffee while he ran to the bathroom. he came back right as you two finished ordering your food and were saying Deans order.

Sam spoke up first, “a Dean will have a burger and a coffee milk and sugar.”

you quickly cut Sam off not noticing Dean walking back and listening, “actually Dean likes extra pickles no onions ketchup on his burger and his coffee black with sugar packets so he can add his own sugar oh and can you bring napkins and a spoon so he doesn’t make a mess?”

the waitress nodded and walked away and Dean sat back down just staring at you for a moment before speaking up about you noticing how he likes his food and coffee without him even telling you.. just because you observe him, “i didn’t think anyone noticed that.”