Dean-
That no matter what happens, even if it's a near death thing going on, he can make you laugh and reassure that everything is going to be okay.
Sam-
How smart he is. He's a major bookworm and he'll read books with you. No matter what they are, he'll read them.
Cas-
You've always loved how much of a lost puppy he is. If he's ever confused, he'll go straight to you and ask and you just think it's adorable.