When Dean goes to his room to sleep Cas follows him shortly after it. Dean goes into his bed, while Cas sits down on his armchair to read a book, his reading for the night is about human behavior. He often reads books about things like this, it helps to understand them better.
Dean wishes him a good night, which Cas returns and minutes later he could hear how Deans breath  takes a steady rhythm.
He now proceeds to take a look at Jack and Sam.
Sam is still awake, looking for another case.
So he convinces Sam to go to sleep and takes the laptop with him, bringing it into the kitchen, where Sam can get it back in the morning.
From the kitchen he takes a few nougat bars and goes to Jack who is watching a show on Netflix. With Jack he spends the next hour talking about the world, trying to help his son, who still struggles to understand it. Things they both don't understand are going to come up while breakfast, where Dean or Sam help them out.
When they're done, he tucks Jack in, gives him a kiss on his forehead and wishes him a good night, following the instructions of the books he read when Kelly was pregnant.
He then goes back to Deans room, to  finish his book,  he is done around 3 am, and then gets his basket with his knitting tools, to work on his newest project.
A pullover for Dean, made out of green yarn, with the same color as his eyes.
At 6 am he makes a healthy sandwich for Sam, who comes around when he's done, saying thank you and disappears with his laptop under his arm into the living room.
Since Dean normally doesn't wake up before 8 am he has a lot of time to make Deans favorite breakfast, which consists out of bacon, scrambled eggs, pancakes and of course a pie.
After he finished making breakfast, he takes a cup of coffee to wake Dean up, on his way to the room he's passing Jack, who tells him that he will set the table.
He's holding the cup of coffee under Deans nose, which is as he found out the most effective and safest way to wake him up.
Taking the cup in his hand he mumbles: “Morning Cas, how was your night?”.
“The usual.”, he answered.
They walk into the kitchen, where Sam and Jack are already eating.
Dean's eyes become wide, when he sees the breakfast table.
“I love you”, he said and gives him a kiss.
They both sit down and while the others eat, Cas enjoys watching his family.
