You can't sleep

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Dean : When you can't sleep you usually wake him up and you two talk for hours until you finally fall asleep.

Sam : When you can't sleep you get up -which wakes up Sam- so you two go for a walk to clear your heads. When you come back you and Sam eventually fall asleep.

Castiel : You would wake up because of the nightmares you have frequently. You were tortured in hell and still can't get rid of the nightmares you get. When this happens, Cas usually uses his powers on you so that you can sleep peacefully.

Lucifer : Lucifer doesn't normally sleep but when you can't fall asleep, he would lay down with you, wrap his arms around you and wait until you finally fall asleep. Even though he doesn't need to sleep, he would then stay with you all night because he knows you like it better when he sleeps with you.

Gabriel : When you can't fall asleep you usually end up get up and preparing pranks with Gabriel for the brothers.

Crowley : when you can't sleep Crowley would whisper nice things in your ear while holding you close until you finally fall asleep.

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