Anyway, back to why I started this article, I think that Sam and Dean having a "happy ending" meaning that they both get out the life, get married and have kids live the normal life, would be the completely wrong way to go in my opinion. Yes, Sam and Dean worked their asses off and even died multiple times in their line of work for mankind, however a decade of them doing what they do and they have became so entwined up in that existence that life outside of it makes no sense for the pair story-wise.
Since day one, for Dean is has ALWAYS been about being a hunter and nothing else besides his Dad and Sam really mattered to him especially after John died. So for Dean to have a normal life outside of the hunting world, for me, makes absolutely no sense at all. Sam on the other hand, he spent his entirety getting away from that world until John died. So for me it's as simple as Sam gets his life free of the demonic/hunting while Dean has to die doing what he believes he was put on Earth for. Which would be unfortunate for Lisa & Ben (if they still remembered), however I see them playing a part in the ending.
The way I see it, the world can NEVER be 100% free of demons/ghosts or anything monstrous the brothers have came across in their time hunting. Far too much has happened with new and evil beings for them truly all to be wiped out. I mean they already closed the gates of hell in Season 2 and there still is countless occurrences of evil happenings (coincidentally only in the US, got to love television shows ha).
So, anyway, back to why I started this piece I wanted to give you guys and girls my thoughts on how I think the show should end leaving me in a state of happiness or as close as can be considering my baby is no more.
Castiel & Crowley
Sam & Dean
So back to what truly matters, what will happen to Sam & Dean, the way I see it the truly happy ending is a no go. For me, Dean has to go out doing what his was put here to do, fighting the evil of this Earth, Dean dying in the line of duty and Sammy is left here to live his "normal life" that he wants.
THE END!
I know I have gone into the details of what I would like to see, however this is how I see the finale actually playing out some specifics. I see Dean on deaths door (specifics I do not mind, as long as it is a serious situation), while on the floor Castiel is over him ready to heal him as countless times before. Dean looks him in the eye and says "it's my time Cas, I can't do this anymore".
While Dean is left dying due to his injuries, Castiel continues the fight with Sam (not sure who or what they are fighting) upon defeating said "baddie", Sam rushes to Dean and starts yelling that he has to stay, there is no life without each other, you know, the typical Sam and Dean back and forth we have seen many a time. Dean continues to tell Sam how he can not continue to do this all the time, at some point they have to die and Dead has had enough and wants the sweet relief he has earned from three decades of of fighting.
Before crossing over, after he has given the Dean speech, he leans in and whispers something to Sam, which we do not hear and also passes him something we can't see. Fade to black, cue Sam knocking on an oddly familiar door, the door opens to Ben, Sam hands him the keys to the Impala and informs him it was his fathers who was a great man (giving him a traditional Winchester speech, we do not hear the specifics of).
"Happy 1st Birthday Dean" is a banner we see hanging above a crib, "Goodnight, Dean" says Sam and the show ends, a nice way to wrap it up, considering that was Dean's first ever words in the show. Sam's now wife, leans over Dean's crib an starts to sing this...
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