WARNING: Spoilers Off applies to this page. Proceed at your own risk.
- Despite his desire to be finally accepted by his people, especially by his father Stoick, Hiccup had enough empathy toward the downed dragon he captured, that not only he couldn’t bring himself to kill him, but he let him free from his trap.
- 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 sells it.
- Also that Toothless shares that first fish Hiccup gives him. Think about it, he'd been stuck in that little cove with limited ability to hunt, and the way he loses patience and grabs it from Hiccup indicates he must've been at the least very hungry if not starving. And yet, despite it being just one fish after being stuck there for quite a few days that's probably not enough to satiate his hunger compared to the several we see him eating per meal later, he still coughs up half of it to share with Hiccup. What a giant puppy.
- Part of Hiccup's Training Montage where he learns how to tame dragons includes discovering that dragons love neck scratches and have a cat-like fascination with moving light spots (essentially a proto-laser pointer). Toothless's expressions are what sell it.
- While also funny, Toothless essentially forcing Astrid to apologize to Hiccup for being a Jerkass by flying extremely fast and erratically, terrifying her. It looks like he's just being petty at first, but as soon as Astrid says "I'm sorry", he stops. It's implied it was Toothless' way of protecting Hiccup.
- 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 subconsciously 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.
- When Stoick leads the fleet off to find and destroy the dragons' nest, Astrid leads Hiccup to realize that failing to meet his father's expectations is not the same as failing his own.
- 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 Red 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.
- It also shows that Gobber is still quick to defend Hiccup, even after his deception's revealed.
- 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.
- 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.
- Especially when you realize that the Terrible Terror's design is the Toothless design from the book.
- The scene where Toothless finally lets Hiccup touch him.
- 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.
- 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.").
- 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.
Hiccup: (momentary Post-Kiss Catatonia)...I could get used to it. - 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.
- A sharp eyed viewer can also see Toothless's pupils dilate briefly when looking at Hiccup while fighting off the Vikings.
- The part after the Red Death is destroyed when Stoick is searching frantically for his son. Toothless (who has Hiccup perfectly safe in his wings) is lying down nearby, and that measured look of cold disapproval he gives Stoick as he mourns the apparent death of his son (his only child) shows that he'll only allow Stoick near after he's realized his mistake. It makes you realize that he's looking out for his friend, to the very end.
- The scene where Astrid encounters Toothless for the first time. She has just been yelling at Hiccup and beating him up for suddenly being so good in dragon training, but when she sees Toothless her first instinct is to push him to the ground and try to protect him from a perceived threat, showing how she's not so bad after all.
- Also, how Toothless and Astrid are both trying to protect Hiccup from each other.
- And then Hiccup tops that by actually protecting them both from each other!
- Astrid wasn't even just trying to protect Hiccup from a dragon; her reaction upon seeing a "stalking" Night Fury is sheer terror, and even as she tries to swing her axe at Toothless she's screaming for Hiccup to run. It's very brief, but it looks distinctly like Astrid's first, unthinking instinct is to pull a You Shall Not Pass! moment on the "unholy offspring of lightning and death itself" in order to buy time for someone she hates to escape.
- After Stoick saves Hiccup from drowning, he immediately dives back in to get Toothless, having accepted that his view of dragons is wrong. Once he breaks Toothless free from his bindings, Toothless carries him to shore.
- It's brief, and not as strong as the other examples listed here, but Ruffnut being able to pull Tuffnut out of a Nadder's fire when they were arguing literally a second before. Later, as soon as she senses trouble, goes to check if he's OK during the Zippleback exercise without a moment's hesitation. As much as they argue like brats, it's nice to know at least one of them's looking out for the other.
- A double moment in the climatic battle with the Red Death - Toothless is trapped and about to drown in a harness. Hiccup refuses to leave him, preferring to drown with him. Doubles - and also doubles as a crowning moment of Awesome - when Stoic saves Hiccup, and then swims back down, where he tears the heavy wood-and-metal harness apart with his BARE HANDS.
- Stoick and Gobber have a great friendship.Stoick: I can buy the men a few minutes if I give that thing something to hunt.Gobber: *clasps hands with him* Then I can double that time.
- After getting back from the dragon's den, Hiccup begs Astrid not to tell Stoick about it because he's afraid his father will kill Toothless. Astrid asks if his "pet dragon" is more important than the island they've been looking after for centuries, and Hiccup simply says yes. What's heartwarming is that Astrid immediately backs down and agrees to give him time to figure out what to do, showing how much she's grown to trust him just from her brief experience with him and Toothless.
- The part at the very end with the perfect capper to the "All of...this" Running Gag. After the gag was used to signify that Hiccup had to stop being himself in order to be a true Viking, Stoick instead pats his son on the back and says "Turns out what we needed was a little more of...this!" The way Hiccup then says "You just gestured to all of me" followed by Stoick's very lovely smile perfects the scene.
- Gobber's relationship to Hiccup is one of the best Parental Substitute Vitriolic Best Buds relationships ever! In spite of all of Gobber's gentle ribbing, he's extremely protective of Hiccup and is one of the few Vikings pre-Toothless who saw more in Hiccup than just a scrawny nuisance.
- Notice how Gobber reacts whenever the twins mock Hiccup early in the film: He smacks them both upside the head.
- As funny as the "breast-hat" scene is in its awkwardness, the fact that Stoick wears part of his (seemingly) departed wife's armor on a daily basis because it "Keeps her close" is quite sweet in its own way.
- Stoick and Hiccup's "Breast-hats". Yes the helmets made from his mom's breastplate was played for laughs, but Stoick's genuine, "keeps her close." comment rings true. In the post movie works Hiccup is seen wearing it proudly.
- Hiccup loses his left leg. You know, the one that's on the same side as Toothless's missing fin. Meaning that Hiccup is using his prosthetic leg to control Toothless's prosthetic tail. Their missing limbs have already been pointed out to be a symbol of their bond, but this small fact really drives that home.
- When Hiccup is brought home to Berk unconscious, its Toothless who rouses and greets him - like a loving household pet, eagerly awaiting its owner to wake up. The dragon was always watching over him, and would not leave the boy's side the entire time.
- Snotlout meets Hookfang. The moment Snotlout puts his hand on Hookfang's snout, the latter starts to purr like an overgrown cat. Snotlout's response is to laugh in disbelief and awe. They instantly bond with each other, which is incredible, given that Snotlout was terrified not moments before, and Hookfang's last experience with humans got him beaten up by a Night Fury.
- The moment itself Hiccup helps Snotlout bond with the Monstrous Nightmare by gently taking Snotlout's hand and placing it on the dragons snout. Watching Hiccup and Snotlout smile at each other over the accomplishment is very adorable.
- Toothless giving Hiccup the vomited up fish. He only does so when Hiccup states that he didn't have any more fish. Think about this from Toothless's perspective: he's probably seen humans before, but the ones he saw were probably very big, burly and strong—by comparison, Hiccup's much smaller and weaker. Toothless must have thought that Hiccup was only able to catch one fish, and yet he'd given the fish to Toothless without taking any of it for himself.
- The Japanese trailer for the movie has this line which perfectly summarizes Hiccup and Toothless' relationship: "The boy gave the dragon wings. The dragon gave the boy courage."
- It's brief, and it's mainly in hindsight, but at the beginning of the movie, a random male Viking gives a cheery "Morning!" to Hiccup before returning to fighting dragons. This was well before Hiccup proved himself in the village's collective eyes, and his reaction stands out as such, being willing to give even the 'village nuisance' a genuine greeting.
- Snotlout, Fishlegs, Ruffnut and Tuffnut immediately get on board with Hiccup's plan to learn how to ride dragons and fight the Red Death. Unlike Stoick, they take no issue with Hiccup befriending a Night Fury and using it to get a leg up in Viking training. And they're willing to believe him about the Red Death and follow his lead if it means saving their families and their tribe. After years of looking down on him, the young Vikings have grown to trust and respect Hiccup as a fellow teammate and a leader.
