Toothless is never late.
He is the one that rises first in the Haddock household - when the dark-blue of the night is tinted with orange and pink and when the village is not yet woken up from its peaceful slumber. He jumps on the roof and wakes the residents of the house, ushering them to see and to admire the sunrise, to appreciate the birds' melodic tunes.
It's the best time for a flight after all. It takes Hiccup a while, but in the end he can't help but agree.
Toothless is first to jump into action. He doesn't trust easily but he holds those who did earn his trust close to his heart, willing to do anything to protect them. And, gods forbid, if there is any danger looming over their heads, he springs into action. He knows they would do the same for him.
With Hiccup, the mutual understanding has reached its peak. They know. It's as simple as that.
Toothless is first to show Hiccup what true friendship means. In the same way, Hiccup is the first one to understand. And the world changes.
Toothless is first to support Hiccup through his otherwise crazy ideas. Whether it's testing their limits or testing the strength of the hearts of their close ones, their dreams, their ideas never falter.
Boundaries in the sky, Hiccup says, do not exist.
And Toothless is first to agree.
But when Hiccup comes to him with a new version of the flight suit, Toothless hesitates, for the first time ever. His best friend, though, is filled with hope, childish hope, with a wide smile, shoulders bobbing up and down in excitement and eyes turned towards the skies.
The next sunrise, they follow their usual routine. The skies are clear. The conditions are perfect. Hiccup sits up and unstraps himself from the saddle.
And lets go.
Toothless was never late.
Until that one time.