One of my Chestervelle headcanons is that Dean likes to cuddle Jo when they're sleeping, but Jo can't sleep when she's being held and will lie there for hours while Dean snores right next to her ear. After many sleepless nights, they both decided that Jo should be the one cuddling and Dean should be the pillow, since then she can just roll over if she feels trapped. This worked a little too well because now they sleep like this all the time:
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