Aaaaaarghghghg go away 😛
Now I’m imagining Dean when he’s upset about stuff (like all those changing phones in season 7 prompting him to keep in regular contact >.>) having long conversations with Sonny about all the shit that bothers him. Probably in very vague terms while he’s angling for that invaluable life advice but even so…
(not that he ever seems to take it, but maybe it’s one of the ways he copes to even make it through some of the worse seasons >.>)
Add that to the fact that when Sam says that it’s someone looking for “D-Dawg”, Dean doesn’t hesitate – he knows EXACTLY who’s calling.
I can imagine Sonny getting a postcard every six months or so with only a phone number and a scrawled “D” and no return address, and filing it away with all the others. He has one from every state in the continental US, and a couple from Canada.