Windshear appears to be comfortable around Toothless, as the two were seen nuzzling. Rather than face him outright, Toothless would rather avoid confrontation altogether even at his the cost of his own discomfort, such as in "How to Pick Your Dragon ". He shows a sense of great curiosity, imitating Hiccup's actions and mannerisms when they initially encounter one another and can understand Hiccup's words and commands as well as agree with some of what he says.
The two of them are always together and have become practically inseparable. From here it was a little bit evident that he sensed goodness in Hiccup. He is one with the dark, flitting through the crack between worlds. Knowing he needed a rider, he wasn't hesitant to put Snotlout on his back so he could rescue Hiccup from the lava of the Defenders' volcano.
He and this dragon have some sort of serious history, and they both are willing to fight to the death over the grudge. Hookfang was attempting to kill Hiccup, and Toothless blasted into the arena in order to save his friend. From here it was a little bit evident that he sensed goodness in Hiccup. After the battle of the Red Death comes to a close, Stoick believes Hiccup to be dead.
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Giant Dick Sucked By granny. So Toothless has an arch-enemy. The dragons openly growl at one another before the games begin. Frost has etched its intricacies across the Barbaric Archipelago creating a glittering floor of ice. However, Toothless becomes distracted after meeting and falling in love with a white dragon dubbed a Light Fury by Astrid. Gobber remarks how hard it is to get Hiccup off of Toothless, and he holds a fair point. As far as can be guessed, Hookfang and Toothless met each other for the first time in the Dragon Killing Arena. I do not understand it, but I cannot deny it.
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Coldwind Wastes. Toothless is fully willing to risk his own life for the sake of his friend. A dry sense of humor, big heart, and a winning smile make Toothless and Hiccup mirror images of each other, and they are rarely out of each other's company.
Ever since then, they were merely curious about each other, but eventually, this curiosity caused them to see each other's similarities. When Toothless breaks free from the Alpha's control and calls other dragons to aid him, Stormfly is the first dragon shown to return to herself and join Toothless' side as he makes his stand. One year after they both became leaders of their community, Hiccup and Toothless still take time to play together despite their duties while also being dragon rescuers. Giant Dick Sucked By granny.
Kit Harington vs Toothless Funny Clip - HOW TO TRAIN YOUR DRAGON 3 (2019)