he and Sam are on a hunt in your school, Dean is 'teaching' your class P.E. and Sam is looking for the monster, as Dean is 'teaching' y'all P.E. he sees that you're the only one that is wearing a hat and long pants, he throws a ball at a boy and signs to you that you need to come with him, talking in the hallway

"Why aren't you wearing your P.E. clothes?"

he says a bit annoyed but also curios, checking you slightly out. Looking at your body