This has to be one of my favorite stories you've written so far...and it's right up there with some of the best short stories I've read in years.
For example, your line:
"This Sam Winchester used to be the only one there was, until the man you are now started to emerge from boyish dreams and confused longings, much as he is trying to emerge from your own jumbled memories and occasional fitful nightmares."
Wow, way to show where his remarkably strong dual nature (which, in the theme of the show is his greatest strength) comes from...it's inherent to his character, as fundamental to who he is as an adult, as his genes are to his humanity. You captured this so perfectly, so exquisitely, I had to read it several times to catch all the subtle nuances...
When I read the last line---
"But this Sam Winchester is the one who loves, more than anything in the world, not Jess, but Dean, and so you know when he says 'All right, I'll come with you,' that no matter whether or not you make it back to the interview on Monday morning, you've lost."
---it elicited such a strong emotional response (delight and happiness being foremost), that, again I found myself rereading it. Why would my reaction be happiness when you ended the story with the words "you've lost"? There is no "lost" for Sam; who he is, as you so cleverly and clearly showed before, what his personality is capable of, is not limited to one persona or the other...he is both, in equal measure, because the path his life has taken, and the path he chose to take, has allowed him this profound inner strength.
Wow, I say it again, what a remarkable work this is...the narrative's perspectives, the strong plot movement, the theme that unfolds so steadily and true (and so beautifully), even the stripped-down nature of the concepts presented (there are no unnecessary tangents, no useless verbiage)---in other words, your story's really focused and tight---makes this a great read all the way around.
Post Script: "Awe"...yep, that's what is it, I feel awe for your skill as a writer...which is why "Wow" keeps popping up---"Wow, Geez" is the definition of "awe"...well, at least here in Ohio (okay, so I penciled it into my dictionary, doesn't make it a deal-breaker, just means your work elicits wildly exclamatory responses when being read...this is a good thing...truly...)
I think part of Sam's troubles in season 1 was that HE thought there was a "lost". He couldn't bring those two halves of himself together. And in a sense, Dean and Jess represent those halves of him: the hunter and the normal girlfriend. The problem is that no one can just bury one half of themselves as if it had never existed. I think it was John dying, not Jess, that really forced him to get his head straight, though.
Thanks very much for the lovely review!
And what's wrong with wow geez? I like wow geez.