Dean- He'll know you're having a nightmare because you'll be shaking and crying softly. After he wakes you up, he'll stroke your arm and tell you it's okay until you fall back to sleep.
Sam- He'll wake you up and hold you in a cradle, shushing you and telling you that you're fine. The monsters can't get you here.
Castiel- He'll enter your dream and make it more peaceful.
Adam- It's usually the other way around. He's been having nightmares about the cage since he got out. He got out before you two reunited.
Whenever he has his panic attacks, or nightmares, you're there to calm him down.
He also will help you with nightmares, but it's usually him having them.
Gabriel- He will calm you down and give you candy.
Lucifer- Despite being the devil, he can be very sweet.
It was four in the morning and you shot up, breathing heavily. You just had a nightmare about your parents death. You'd been having these nightmares since you were young.
"You okay," he asked, a hint of worry in his voice.
"Is the Devil showing sympathy," you laughed.
"Are you okay," he asked again.
"Maybe," you loved annoying him. You knew enough was enough though.
Eventually, you talked about the nightmare, and he would comfort you.
Michael- He'll rub your back and trying his best to calm you down. He'll also read to you after he managed to calm you down. That's your favorite part.
Sammandriel- He doesn't really know what to do. He'll talk with you about what happened in the nightmare, but you don't really expect much from. Who knows? Maybe one day he'll surprise you.
Chuck- He'll be somewhere else, for whatever reason, and you'll just grab your notebook and start writing. You weren't planning on being an author, but you did have skill.
Kevin- He'll make sure you're okay, and he'll make a midnight snack for the both of you and watch a movie. It's always funny because Dean will come out yelling at you to turn the television off.
Ash- He gets Ellen. He doesn't know what he's supposed to do, so he goes and gets Ellen.
Gadreel- Neither of you sleep. It's as simple as that.