awabubbles:

Headcanon for when Jack works with Dean and Sam on a case. He calls them “boys”, at first to belittle them because he knows it’ll piss them off (especially Dean). ”So boys,” “Well, boys”, “Keep up boys!” 

And in turn Dean has a plethora of names for Jack playing off of his role as Captain. “Captain Douchebag”, “Captain Suspenders”, “Friggin’ Captain Planet”.

Eventually the pet names become endearing. Jack may even slip once in awhile and say “my boys”.