1. The shotgun seat
When Castiel is back on the road with the Winchesters again, he doesn't ask for a shotgun seat, but Dean knows. So, Dean throws the key to Sam, "You drive, I'll sleep in the back", he instructs and slides himself into the backseat. During the ride, Castiel is content with the view from the front seat. Dean is happy.
2. Four Hours.
'Watching over' is a little too creepy for Dean's liking. So, he forces Sam to let Castiel use the laptop, then teaches him how to use the internet. So that when Dean's getting his four hours, Castiel will have something to do.
3. The Badge
"Okay, come over here" Dean takes Castiel photo and orders a new FBI Badge for him (Along with CDC Health Inspector). Dean knows Castiel has lost the first one, so he makes him a new ones. No big deal. Right, agent Still?
4. TV
Dean doesn't comment on any show. He doesn't pick the channel. He'll watch anything that Castiel decides to watch even if it's just space channel with nothing but a picture of earth from a satellite. One in a while, they will talk about what's on TV and what's next. But Dean never picked the show, he'll let Castiel have the remote.
5. Cats
For whatever unknown reason, Castiel likes cats. They find stray kittens by one highway. They don't know where it's from. Castiel wants to help them. Dean obliges. Instead of going to a local shelter, they go to a playground with lots of children. Dean has Sam made a sign 'Kittens for adopt'. The kittens find new home. Castiel smiles, and so does Dean.
6. The duffel
Dean doesn't mind Castiel going through his stuffs. Then Castiel notices something different. There are two toothbrushes in Dean's personal hygiene purse instead of one. 'Whose is this?' he asks himself. It's like Dean can read his mind. Dean says "In case you want it" and shrugs the topic off like the second toothbrush is the most normal thing in the world.
7. The necktie
You see, Castiel's necktie is backward. It looks unconvincing when they're investigating a witness, so Dean takes it as his job to flip it to the right side. Then he will seize an opportunity to twist it back. "This is more like you." Dean comments. Castiel is Castiel because all his imperfection which is endearing to Dean very much.
8. Hamburger
Dean has always ordered two hamburgers anyway. So, it is absolutely normal that he still orders two, then shares one with Castiel. Angels do not eat. But Castiel still says 'This makes me very happy' and Dean's heart swells twice the size.
9. John's journal
Castiel loves to read John's journal even though he has memorized it completely. Sometimes, when he flips the page, Dean will add his side of the story. Then suddenly, a journal is not just a stack of information. It's Dean's journey too, and he wants Castiel to know beyond the pages.
10. Words.
Dean never says the L word. It has never even crossed his mind. He only promised that whatever monsters coming their way, they will handle them together, and that Castiel doesn't have to be 'useful' besides him. Castiel just has to be Castiel, and with Dean. That's all Dean needs