Secondly, one other thing: this is the first time we've seen the boys really dealing with/celebrating Christmas. Judging by the way time was handled over the summer (6 days and all), this is also the first year they've celebrated Christmas with John dead. In a very real way, John isn't with them for Christmas and unlike when they were children, there's no hope of him ever coming, ever being there. I imagine that might be an especially hard Christmas for Dean and why he needed to do something: not only is it his last one, but it's one where his usual companion (John, for the last few years) is gone. Dean Sam yey, obviously, but for a while it was just Dean and John.
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Secondly, one other thing: this is the first time we've seen the boys really dealing with/celebrating Christmas. Judging by the way time was handled over the summer (6 days and all), this is also the first year they've celebrated Christmas with John dead. In a very real way, John isn't with them for Christmas and unlike when they were children, there's no hope of him ever coming, ever being there. I imagine that might be an especially hard Christmas for Dean and why he needed to do something: not only is it his last one, but it's one where his usual companion (John, for the last few years) is gone. Dean Sam yey, obviously, but for a while it was just Dean and John.