I'm really starting to think it'll be the other way around.

Me too. After all, Sam probably said yes in The End because he had nothing left in that future. The same could be said of Dean now. Of course he has to take care of Sam and save the world, etc., but at this point it almost seems like he's worrying about that out of habit, and I'm sure that if someone could somehow convince him that he could save Sam and everyone else by saying yes he would do it.

And god, 6 weeks? Is it because of the Olympics?