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I'm only in the middle of season 5, but hey, here's season 1 Sam
Okay, sure, drag me around. Technically I'm already on a... road trip. Extended. Road trip.
[That's what he's been doing, but — he can't say he's been enjoying the events back home. Last he checked, dad was in piss poor shape and Dean wasn't fairing much better, either. Guess that's what happens when demons fuck your shit up, but he's starting to wish life was just a little less complicated (like he does just about every day).]
And that road trip is pretty messed up right now; I'll let you know when I'm actually interested in all this future crap you're being tight-lipped about when I get my hands on that yellow-eyed demon, finish this once and for all. Once that's all over with, I'm not gonna be worth much for writing about.
I mean — whatever happens after that can't possibly be anything we can't handle.
... Right?
((ooc: spoilers are okay with me, just as a reference (so this is also a warning there may be spoilers in comments); I'm already plenty spoiled on the last 3 seasons too
JUST STRETCHING MY WINCHESTER LEGS :|b))

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She shakes her head. ]
Nope. You're not dreaming at all. [ She takes a step closer and tilts her head to the side. ] I can pinch you if you wanna prove it.
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He'll get around to it. He's got things he couldn't really say to her before, so he'll say 'em now, even if it doesn't count for much. Swallows the lump in his throat.]
I'm so sorry, Jess.
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I know. [ All too well. ] It's not your fault.
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I should've told you. About — everything.
I screwed up.
I should've been there.
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Sam, you couldn't have been.
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I saw you die. Before — I dreamed —
[He bites back his reply to steady himself.]
I dreamed that you'd died. If I were more careful and I didn't keep any of it from you, you might still be here.
[Even if she didn't want to be with him after hearing everything — at least she'd be alive, and that's all he wanted, in the end. It wasn't fair, how everything ended. She deserved everything. And he took it, whether he meant to or not.]