[Hmm. Maybe sometime right after Dean stopped being a demon (but still has the Mark) and we assume either Cas is trying to keep an eye on him or Dean's having nightmares or something. Or maybe from when Cas was human and in the bunker (and we pretend kicking Cas out of the bunker didn't happen, or it did happen and this is after Cas comes back) and HE'S having nightmares or is cold or having trouble being human. Or we could AU the end of the series and have them end up together.
Those are just a few off the top of my head, but open to other options if you have ideas.]
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Those are just a few off the top of my head, but open to other options if you have ideas.]