Okay, my first thought on reading this was ‘yikes did he rOLL THROUGH THE FIRE?’

Then I thought, welp… kay, so this is Sansukh alone, and everyone else’s headcanons are totally true for them, but since you asked for it, here’s mine. 

For the first part of the Quest, probably not. I think that through long habit, Thorin sleeps like a warrior and a traveller, though it is not natural to him. He has learned to sleep silently, and to fall asleep whenever the opportunity presents itself (because who knows when the next rest will be?). He has learned to sleep nearly totally motionless: his arms pulled tight to his body, his weapon lying by his hand (sheathed of course – having a naked blade nearby when you are sleeping is a Bad Idea). On particularly cold nights, he might end up sleeping back-to-back with his nephews or Dwalin or perhaps Gloin (they’re all family, they can be trusted) to preserve body heat. But not Mr Baggins. A certain burglar was not exactly in favour for quite a while there. It took some time for Bilbo to prove himself, after all (and stop moaning about his kettle and garden and books and hankies, lol)!

During the second part of the quest, that’s all different. I can imagine Thorin absolutely stumping the Hobbit by asking him to sleep by him, the same way his family have done, so they might share warmth against the chill northern air. After all, the rest mostly have their siblings to sleep beside, and it is only Mr Baggins and Thorin who remain alone. It’s only practical, Thorin would tell himself. Yes, only a matter of practicality. 

Mr Baggins, for his part, would splutter a bit and make all those rather endearing dumbfounded faces he was so good at, and then he would eventually agree. He would be a little skittish at first as they bunked down beside each other, but Thorin would pretend not to notice, and they would eventually chat in low murmurs about the Shire, about their journey, about what route they should take and what they were likely to find over the next few days. And about Erebor, naturally.

Perhaps it is an indication of how relaxed Thorin was, but for the first time in long years he did not sleep as a warrior and traveller does: deep and still and silent. No, he woke up the next morning with a snuffly, soft little armful. His own mouth was open and a little dry, and he had apparently been softly snoring – he usually only snored when he had been in his cups. He was terribly warm, and there was Hobbit drool on his forearm. 

And his Company were awake and sending him amused little glances every now and then.