Winchesters are terrible examples of normal human psyche. Pitch will have fun with any that come to the city until Cas asks him to knock it off.... then he will.
Pitch is actively less of a vindictive asshole than Crowley though. He's happy with his existence when he's not being walked through and slowly killed. :|
also I heard we're getting stuck in one party in Lily's dreamscape, but I'm still getting to replying to Sokka-mun's tag there orzunless you wanted to go first