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- The Forbidden Friendship scene where Hiccup tries to approach Toothless close up. When Toothless sees him drawing a picture of himself, the dragon tries to draw his own version on the ground around him, to a light twinkling melody on the soundtrack. When Hiccup learns that he must not step on the lines of Toothless' drawing, he effectively goes into a dance avoiding them, climaxing when he is face to face with the dragon. At that moment, Hiccup takes a leap of faith, averts his eyes and reaches out for the dragon; when Toothless touches him in response, it is an act of trust that will begin to change everything about both their worlds.
- The little uncertain false start that Toothless gets just sells it.
- Astrid's first flight with Toothless, in which she goes from hardened warrior to awestruck teenage girl (and no, in this case that's not a bad thing). Especially the moment when she unselfconsciously wraps her arms around Hiccup and leans her chin on his shoulder - judging from the look on Hiccup's face, that's just as amazing as the flying itself.
- Astrid's little talk on the top of the wharf after the vikings left for killing all the dragons
- The ending where Toothless helps Hiccup walk with his new artificial leg. Also the five minutes preceding that scene where Toothless has Hiccup covered in his wings to shield him from the explosion. Warning: these scenes may reduce you to tears.
- If not then the music that plays during the scene when Hiccup realizes he's missing his leg will.
- Toothless' tail sweeps into frame as he helps Hiccup to the door, and you realize that their bond will be stronger than ever before since the boy & his dragon have another thing in common.
- "I'm proud to call you my son." There's a moment in a parent's life where you suddenly look at your child and think, "Wait a minute, when did you become this person?" and it's usually when they're around Hiccup's age. He's spent his whole life being a disappointment to the village because he can't be what the rest of them are, so that's really all they know of him. But when the Green Death is laying waste to all of the vikings and their ship, and Stoick is prepared to die just for a slight advantage, the children come flying in on dragons, overturning generations of belief. All the time Hiccup has spent working with Toothless is reflected in this moment, when he and his peers and doing something no one else ever dreamed of. When Stoick says he's proud of his son, it isn't because Hiccup has met the standards that everyone else has already set. It's because he's done something amazing, on his own, and developed into a strong and independent person that his father didn't even realize was there. It's truly an emotional moment in any parent's life.
- A close second to this one - the scene as the kids arrive on the dragons, Gobber turns to Stoick and points out that Hiccup is just as stubborn a viking as Stoick ever was. The look on Stoick's face as he nods in response to this comment is a testimony to the CGI artists' skill.
- This troper melted when, after Toothless refused to share his food with the Terrible Terror, Hiccup did. The tiny dragon then cautiously approached him, then curled up and fell asleep under his hand. AWWWWW!
- The scene where Toothless finally lets Hiccup touch him. This troper doesn't know a single person who didn't melt at that scene.
- What makes the drawing part even more heart-warming...Toothless gets "inspired" to draw something after watching Hiccup do a sketch of him in the dirt. As he draws, he looks back at Hiccup for a moment before returning to the drawing. And then the Late to The Punchline moment passes and one realizes he was trying to draw Hiccup. Furthermore, after Hiccup gets the idea that he mustn't step on the lines, he effectively goes into a dance stepping around them, with the score playing "Forbidden Friendship" until he winds up in front of Toothless and then he takes the above leap of faith.
- EVERY scene with Toothless. He's like a big kitty in dragon form. This troper wanted to glomp the screen, he was so cute!
- When Astrid punches Hiccup ("That's for kidnapping me!") and then gives him the most adorable shy-girl kiss on the cheek ("That's for everything else."). Say it with me now: d'awwww!
- And then at the end of the movie... After Hiccup walks outside, seeing the Vikings and dragons getting along peacefully and working together, Astrid punches his arm again, saying "That's for scaring me! (in reference to his Disney Death). Then when he protests, she kisses him right on the lips. The rest of the line goes unspoken, but is heavily implied.
- Necessarily brief, as it occurred during the Final Battle: when Toothless snatches Astrid out of mid-air, he looks around to make sure she's all right. She smiles back, and his eyes dilate and he makes his "happy to see you!" warble. He likes her!
- A heartwarming moment in very tense and terrifying scene: Toothless stopping immediately from blasting Stoick in the ring when Hiccup screamed at him to stop. The absolute trust he has in Hiccup, so much so that he stopped the attack completely is beautiful, and made his subsequent capture even more gut-wrenching.
- Just about the entire "Gift of the Night Fury" short, but especially the titular gift. After being given an interlocked tailfin so he can fly independently, Toothless uses it to retrieve Hiccup's helmet, returns, and then systematically destroys it, insisting on the old saddle and tailfin - and his bond - instead.
- I loved the scene at the begining of "Gift of the Night Fury" when a small chlid (wearing a dragon costum no less) growls at Fishlegs' Dragon, the Dragon responds with a small growl of it's own. What does the girl do? She giggles!
- In "The Book of Dragons," it's of course Hiccup who gives the lesson on Night Furies. When talking about Toothless, he comes to this touching line:
Hiccup: I have so many questions about him, but there's one thing I do know. Toothless didn't just become my friend. He became the friend who gave me my purpose.
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