Thinking about the 300th episode and...
We know the Winchesters got that one dinner as a family. I've written before about how John and Mary might have (for the first time) shared stories of the boys as kids. But like... SO MUCH happened after John's death that would blow his fucking mind. So, on a more lighthearted note, some brief interactions that I imagine at the dinner:
Dean: Oh! Dad, guess what?
John: What?
Dean (with Sam and Mary mouthing along): I killed Hitler!
John: ...what?
Dean: :D
___________________
Sam: Anyway, turns out the girl I took to prom was a demon...
John: Aw shit, Sammy, I'm sorry...
Sam: Some of my teachers were too.
John: This is why I needed to move you boys around so often. How did you find this out?
Sam: Lucifer showed me while he was possessing me.
John: ... THEE Lucifer???
Sam: Yeah. He spent a long time trying to jump my bones.
Dean: And then when that failed, he jumped Vince Vincente's bones.
John: That hair-rocker??
Dean: And then the president.
John: Am I being pranked right now? Is that what this is?
Mary: Dead serious-- but the devil is dead now. His son is such a sweetheart, though!
John: w h a tttt???
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Sam: Hey Dean, remember the suicidal teddy bear?
Dean: Weirdest shit we ever hunted.
John (to Mary): THIS is the prank, right?
Mary: I.... I don't know...
Sam: I think being stuck inside an episode of Scooby Doo was at least as weird as that.
Dean: But way more awesome.
Mary: Now, that DID happen.
John: Don't you boys ever just kill werewolves anymore? ;-;



















