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(1)
He can't bring himself to kill the dragon, so he frees it.

The dragon has no such reservations.

He wakes up in his bed.


(2)
He knows what went wrong with his invention, but he doesn't have the time, doesn't have the chance, to fix it - all he can do is disable it.

The Night Fury is unhindered.

Two weeks of struggling through his lessons, and then he wakes up in his bed.


(3)
Ruffnut catches him and throws him off a cliff, and he wakes up in his bed.

Snotlout shoves him into just the wrong place during dragon-fighting training, and he wakes up in his bed.

His desperation to repair his invention overcomes his learned caution, and he wakes up in his bed.


(4)
He catches the Night Fury.

He kills it.

He wakes up in his bed.


(5)
The Night Fury finds him, eyes furious and - betrayed?

'But it's too soon!' he thinks, 'The raid hasn't even started yet!'

He wakes up in his bed.


(6)
He catches the Night Fury.

He talks to it.

He sets it free.


(7)
The villagers of Berk find them.

Hiccup tries to talk to them, these people he's known all his life.

The dragon is a better listener.


(8)
He wakes up in his bed.

He goes to the clearing.

The Night Fury is already there, waiting for him.


(9)
Hiccup is growing reckless, seeing consequences washed away like the wood Spitelout tried to store in the sea.

The Night Fury (who accepts the name Toothless, as joke and reassurance and shared familiarity) scolds him for it, not truly understanding what Hiccup has realised - that time folds in on itself when he dies, that there might not be such a thing as permanence anymore - but Hiccup ignores him, until his reckless acts get Toothless killed instead of him.

He isn't sure he's ever been so relieved to wake up in his bed.


(10)
Toothless bounds to him as he gets to their clearing, looking him over frantically, then puts his nose in the air and turns his back on Hiccup.

It's fair, more than fair, Hiccup knows that, but when his wheedling falls on deaf ears he finds himself getting more and more frantic - the repeating time has been good for him, knowing that no one who matters to him (Gobber, Stoic, Toothless himself) will die or even be injured in any way that won't be undone the next time he wakes up in his bed, having freedom to experiment and learn things without having to worry that he'll use up the last of the village's patience because it won't matter even if he does, and he hadn't realised until now how reassuring the presence of someone else who's aware of the repetitions is, how much he needs it.

Thankfully Toothless forgives him, turns around and accepts his desperate apologies, and waking up in his bed might be good but it's nothing compared to waking up from a nap to find Toothless' wing tucked around him.


(11)
He's ashamed of how long it takes him to figure out that something is wrong, that none of the dragons want to attack Berk, that they must have a reason to. Toothless refuses to explain, so Hiccup spends long days learning to win the trust of the dragons held captive for training, learning not to betray that trust as soon as he's gained it (a harder task than it sounds with all of Berk unknowingly arrayed against him), learning how to ride a dragon (and Toothless grumbles in startled jealousy every time he sees Hiccup clinging to someone else).

It takes much longer to survive reaching the Nest for long enough that he can see, can understand, can fear the Queen the same way the other dragons do.


(12)
"There's something... strange, about Hiccup recently," Stoick says to Gobber, who nods grimly.

"It's like the boy just woke up one day a completely different person."

(Pressed against a nearby wall, Hiccup stares blankly ahead as he realises he never gave a thought to how much he must be changing, how strange it must be to everyone who hasn't shared the time with him... how in some impossible to describe and yet chokingly real way, he's leaving everyone else behind.)


(13)
(How can he stop leaving everyone behind? How can he keep everyone alive through the raid and everything that follows, instead of relying on time to repeat itself and restore everything the way it had been?

...How can he ever become man enough to respect himself if he spends forever being this weak child?)


(14)
"Toothless. We're gonna do it.

"We're gonna figure out how to defeat the Queen."


(15)
They can't do it alone. They can't do it together, not just the two of them.

It's a fluke, a coincidence, that has Hiccup seeing similarity between the Nadder and Astrid, but once he does the thought drops into his head ready-formed as if it was just waiting for him to think it: why should he be the only human to partner with a dragon?


(16)
He doesn't mean to hurt Stoick, not the way he can see he has, but if he has to choose - if Stoick is going to demand he choose - how can he choose anyone but his partner? (How could he dare to choose anyone but the person who'll remember his choice?) (How could he want to choose anyone but the only person who's chosen him?)


(17)
There are so many slips, they're making so many mistakes, and if Hiccup didn't know he could repeat this until he gets it right he thinks he might be paralysed by how terrible the risks they're taking are. (Banishment and injury and death and death and death, the memories threaten to drown him - so much suffering he's gone through already just to see this enemy, and here he is blithely leading these unblooded idiots along as if he doesn't know exactly how much they will be hurt when this kills them.)

This is just a trial attempt, he tells himself, he's just seeing how far they can get so he knows what to prepare against the next time, and he keeps on believing that until the Queen is struck-dying-doomed and her death throes sweep him and Toothless together from the sky.


(18)
He wakes up in his room.

He wakes up to Toothless beside him in his room.

He wakes up to the loss of an outside tension that had grown so slowly he never noticed it, and realises that time will not repeat itself again.


(19)
None of them died, he hears and can't quite believe, none of them died despite how unprepared they all were, none of the dragons died at the hands of the Vikings and none of the warriors-in-training he led to become dragon-riders died at the jaws of the dragons and none of them died. He and Toothless are the two worst-injured, his leg and half of Toothless' tail - "It's right for the leader to face the worst threat," Stoick says awkwardly, and Hiccup sees with disbelief that his father is proud of him.

The rest of his dragon-riders come to visit, and he sees with even more disbelief that his father is not the only one.


(20)
Hiccup draws up plans for an artificial tailfin for Toothless, not thinking to hide them because he's grown so unused to consequences mattering, not seeing how those around him take this sudden new boldness.

He can grow up now, in a village where Vikings and dragons work together, where he's respected without having to pretend to be like everyone else, where his brother is accepted beside him and no one is forced to raid for the Queen.

He thinks Toothless agrees with him that all that is worth the price of one tailfin and one leg.



Set of headcanons about this 'verse here
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