You see this happened wayyy back in 2007
Let me just explain.
See we woke up on a Tuesday. we went and did some stuff and got to the point where we had to break in and stuff at night.
and I somehow ended up getting shot and killed.
Then Sammy was sad and crying and stuff
and out of nowhere He woke up again AND IT WAS TUESDAY AGAIN.
So it pretty much rolled like we did stuff and I died a gazillion times and every time I died Sam would wake up again and it would be Tuesday all over again and only he knew that is happened all over again except for the trickster or Gabriel ( the archangel ) who was running the show.

And I might mention that you can watch this happen in season 3 episode 11 of Supernatural :D