being your assigned guardian angel was definitely more of a harder task than Castiel had initially anticipated as he figured you would’ve been the easiest out of your brothers — the other two stubborn Winchesters that he’d both helped greatly.

“you were never a good listener, were you?” Castiel observed blatantly whilst his hooded eyes raked over your tensed figure in the middle of the woods he graciously and kindly guided you after dragging you from Hell — your stubbornness leading you to take over Dean’s position.

he was ultimately felt dumbfounded on why you would’ve volunteered to suffer for months and yet, he didn’t bother to ask knowing you would’ve shot back with a snarky remark to his obliviousness.

Castiel raised a brow in curiosity, “why do you not listen to me? i know how to help you and yet, you don’t bother to take it.” he commented hesitantly as if the words would trigger you to lash out, saying you ‘were better off alone’ like Dean had been always said.

you never listened even in desperate or otherwise tough situations on hunts that you clearly needed help in — it truly baffled him at how stupid you were, thinking life would be easier if you didn’t take help.

Castiel still watched over you from the shadows or through his invisibility as a part of him eventually grew more worried at your obvious lack of consideration to your well-being.

Castiel frowned, “it’s okay to need help.” Castiel reminded you in a way that showed his reassurance and fondness towards you without physically speaking it or showing it, knowing you would take after Dean and shove it into his face.