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The relationships of Hiccup throughout the How To Train Your Dragon series.

Family[]

Stoick the Vast[]

I was so afraid of becoming my dad mostly because I thought I never could. How do you become someone that great, that brave, that selfless? I guess you can only try.
―Hiccup, about his now-deceased father.

Hiccup's father is the Chief of the village, making Hiccup himself the next in line to become Chief. However, the two seem to be complete opposites of each other: whereas Stoick is large, strong, brawny, and the best dragon fighter in the village, Hiccup is lanky, weak, brainy, and perhaps (initially, at least) the worst dragon fighter on the island. Their relationship is strained because of these differences, as Hiccup wants to make his dad proud by conforming to Viking norms and attempting to slay dragons, but ends up making things worse most of the time. also

Though confused as to what to do about Hiccup's peculiarities as a Viking, Stoick is very protective of his son due on what happened to Valka; he is at first reluctant to send Hiccup to Dragon Training for fear that he will be killed. Moreover, during a dragon raid, it is shown that Stoick, along with everyone else in the village, prefers that Hiccup stay inside and out of harm's way (though this may be because Hiccup is more of a risk to the village than the dragons are to him).

Stoick becomes proud of Hiccup when he hears of Hiccup's success in Dragon Training and is elated to finally have something in common with his son, although his attempt at conversation with his awkward son ended in failure. However, after his son's relationship with Toothless is revealed, their small progress with one another is destroyed. Stoick accuses Hiccup of siding with the dragons and later no longer considers Hiccup to be his son. Their relationship is later mended when Hiccup comes to the rescue of the older Vikings during their confrontation with the Red Death with the help of his classmates and the dragons used in training, showing his dad his otherwise unseen bravery and leadership. This causes Stoick to apologize for his prejudice against dragons and say that he is proud to call Hiccup his son. Stoick shows how deeply he cares for Hiccup when he believes that Hiccup is dead and mourns, apologizing for not having listened to him before. He shows great happiness when he learns that Hiccup is still alive thanks to Toothless' efforts. Later, Stoick and the village welcome Hiccup as a hero and Stoick finally accepts his son for who he is.

In the television series, Hiccup is given the responsibility over the dragons. However, partly due to Stoick's emotionally inarticulate nature and moments of unintentional insensitivity, his father's approval and acceptance still proves to be a major source of insecurity in Hiccup's life, and he is shown to go to great lengths to confirm that his father really is proud of him. In Portrait of Hiccup as a Buff Young Man, after being painted stronger than he is, Hiccup sets out on a treasure hunt that Stoick failed to prove himself. Stoick apologized at the end for making his son feel he had to do something big to be accepted. A more accurate picture was placed in the Great Hall to replace the other one. In Thawfest, Hiccup was determined to finally beat Snotlout. When he decided to throw the race, he apologized to his father, and to himself, in his choice. Though Stoick was still proud of Hiccup in how well he'd done.

The two still often have a hard time communicating with each other. In How to Pick Your Dragon, Stoick seems to ignore Hiccup's teaching about how dragons need trust. Gobber told Hiccup that "it's a father's job to listen to his son, without letting on that he's heard a word".

Stoick is still very protective of his son. After Hiccup and Toothless were kidnapped by the Outcasts, he banned flying dragons to try to keep him safe. While Hiccup respected his father, he felt he had to go behind his back in case Alvin attacked. The two later reconciled. In Frozen, Hiccup was very concerned about Stoick being paralyzed by the Speed Stingers.

Hiccup is also shown to care for his father. Hiccup was very determined to rescue Stoick from Dagur's clutches when Stoick was taken hostage as a trade for Toothless in Cast Out Part I and Cast Out Part II. Hiccup was even willing to join forces with Berk's enemy, Alvin The Treacherous, just to save his father.

In the second film, their relationship is strained because Stoick has decided to make Hiccup Chief of Berk, but Hiccup is reluctant to take on the duties and avoids him. But it was restored after Hiccup found Valka, the two work together against Drago Bludvist. When Hiccup is threatened by Toothless, who was hypnotized by Drago's Bewilderbeast and ordered to kill Hiccup, Stoick runs to Hiccup's aid and pushes him out of the way right before Toothless fires a plasma bolt, killing Stoick. Hiccup is devastated, to the point that he yells at Toothless when he resurfaces, even though it wasn't his fault. Afterwards he shoot a flaming arrow as his funeral along his friends and mother.

After Stoick's funeral, Hiccup says he was afraid of becoming chief because he didn't know how to live up to Stoick's job, showing that he had a great deal of respect for his father and what he did. He then decides to continue his father's legacy and becomes Chief of Berk to honor him and not let him die in vain. all the problems that they have with each other, Hiccup and Stoick are shown to love each other very much and are willing to sacrifice their own happiness and lives for the sake of the other.

Valka[]

All this time, you took after me. And where was I? I'm so sorry, Hiccup. Can we start over? Will you give me another chance?
―Valka, eager to reconnect with Hiccup.

Valka is Hiccup's mother. She was believed to be dead for twenty years and that she was taken and eaten by dragons. She was taken when Hiccup was just a baby, so he hardly knew anything about her. In the film, Hiccup was given a helmet made from her old armor. While though he found it awkward at first, it is very important to him, as seen in Gift of the Night Fury. In Breakneck Bog, Hiccup is willing to face extreme danger, and a possible Fog Monster, to retrieve a lost gift from his mother. In How to Train Your Dragon 2, Hiccup not only reunites with his mother, but learns she has been living with, and rescuing dragons. Throughout the second film, she helped him discovering his identity as a Rider and a leader. In the end, Valka stays with him on Berk and celebrated along wtih Gobber,Astrid and the rest of the villagers her son's coronation as Chief of Berk. like his father, Hiccup is shown to love his mother very much and like her to be in his life again and Valka is willingly to sacrifce her happiness for the sake of his.

Astrid Hofferson[]

What, is it always going to be this way? 'Cause... [Astrid kisses him] ... I could get used to it.
―Hiccup in response to Astrid punching him.


How-to-train-disneyscreencaps

Hiccup and Astrid.

Astrid is Hiccup's main love interest in the series and fellow Dragon Training classmate in the first movie. At first, she is unimpressed by Hiccup and his lack of dragon-fighting skills, and often rebuffs his efforts to speak to her. Although she doesn't make fun of him like the other Viking teens, she does not seem particularly pleased about his presence in the Dragon Training class either, and probably thinks that he is weak. Later, however, Astrid becomes jealous and angry about Hiccup's sudden success in Dragon Training and follows him into the forest, eventually discovering Hiccup's friendship with Toothless and threatening to reveal it to the village.

After Hiccup and Toothless take her for a ride, her views about dragons and Hiccup change as she sees just how amazing dragons really are as well as Hiccup's true aptitude for communicating with them. She also grows a greater respect for Hiccup when he shows his adamancy in protecting Toothless, refusing to tell the other Vikings about their trip to the Dragons' Nest and his friendship with the Night Fury out of fear that they would take drastic action against the dragons and kill Toothless. Astrid later tries to help Hiccup during his Dragon Training final exam when the Monstrous Nightmare attacks him by distracting it and later holds Hiccup back so that he doesn't get hurt when the Vikings overpower Toothless.

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Hiccup and Astrid's first kiss

Astrid comforts Hiccup and inspires him to round up the other Viking teens to help him with his plan to save the villagers from the Red Death shortly after they depart for the Nest. When Hiccup is believed to be dead, where as everyone else hangs their heads in shame she's brought to tears obviously mourning the loss of her friend (and potentially mutual love interest) meaning she took it the hardest. She finalizes her feelings for him at the end of the film when she kisses him on the lips, implying that the two may have some sort of romantic relationship (emphasized in Gift of the Night Fury where she kisses him again and gives him a hug, and he calls her "Milady"). However, outside of these situations and despite this mutual attraction, in Dragons: Riders of Berk it's shown that they do not consider themselves to be in any official relationship, often shying away from each other (such as separating after finding themselves holding each other, or scooting away when others point out how close they are sitting together). Nevertheless, the two still have a very close and trusting relationship, Astrid being Hiccup's best friend after Toothless, regularly confide in each other and are usually the first to volunteer aid to each other.

In Thawfest Astrid is especially disappointed and upset by Hiccup's new-found arrogance and unpleasantness as he scores more points against Snotlout, and admits to Hiccup being a gracious loser is a thing she's always liked about him. When Hiccup repents his behavior by throwing the race, Astrid is all too happy to have the old Hiccup back and kisses him which happens to be the only time in the TV series that they kiss. She continues to aid Hiccup as his second in command at the Dragon Academy, with the pair of them acting as the "straight men" against the bickering, neuroses and dysfunction of the other teens. In Dragons: Defenders of Berk, Hiccup gives Astrid more responsibility by allowing her to creating training missions for the Dragon Academy/Flight Club. In Fright of Passage, Hiccup tells Astrid that training dragons aren't the only thing that he thinks about. After Astrid said "Are you actually saying that to me with a straight face?", it was made official. Later, during Cast Out Part I, Hiccup gets mad at Snotlout for, not only disobeying him again, but nearly getting Astrid killed in the process and suspends him. This shows that he truly cares for Astrid and will do anything to defend her.

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Hiccup and Astrid's relationship in HTTYD 2

By the time of the sequel, Hiccup and Astrid are an official couple, she even teases him in an affectionate manner. They are comfortable sitting very close to each other, as opposed to in Animal House when they nervously moved away from each other. By the time of the sequel film, Stoick has grown very fond of Astrid because of her romantic relationship towards Hiccup and has even called her his future daughter-in-law to Spitelout during her victory in the Dragon Races. Astrid is the only one Hiccup confides in about his doubts about becoming Chief of Berk and is often talking to her about how his father keeps on pressuring him to take his place. Understanding her boyfriend's concern, Astrid comforts him about his doubts and says what he's searching for isn't in the places he explores but what's inside him. 

Hiccup and Astrid both make the discovery of the destroyed base of Eret, Son of Eret and Hiccup saves Astrid after she falls off of Stormfly (who was caught in a net by Eret's men). After they land, he stands protectively in front of her when they confront Eret. Hiccup and Astrid later perform mutiny against Stoick and head off towards Eret's ship so that he can take them to Drago to change his mind about dragons. During that time, he jokingly throws a net over Astrid and leads her tenderly yet sternly towards the prison cell on the ship so that she wouldn't harm anyone on the ship with her axe. Astrid later tries to follow him when he goes off to search for Drago himself, but is stopped by Stoick and is ordered to lead the others back to Berk since he had about enough mutiny for one day.

Later, when Hiccup and Stoick fail to show up, Astrid leads the other Dragon Riders on a hunt to find them. After that, they are captured by Drago Bludvist, Astrid says that Hiccup will come and rescue them, bragging about Hiccup's role as the Dragon Master and of Toothless. When Astrid finally reunites with Hiccup on the back of Stormfly with Eret, she get's introduced to Valka and is surprised that she's alive and Hiccup jokes to her about how that's where he got his dramatic flair. After Stoick is killed, Astrid rushes to Hiccup's side and holds him tenderly in her arms as they mourn the loss of his father and the Chief of Berk. Hiccup later on leads the shooting of the flaming arrows during Stoick's Viking funeral and Astrid, along with the other Dragon Riders, Valka, Eret, and Gobber all follow his lead. 

Astrid and Hiccup kissing HTTYD2

Hiccup and Astrid's fourth kiss

Astrid is later looking at Hiccup proudly as he takes on his new role as Chief of Berk and follows his lead back to Berk on the backs of the baby dragons. After Hiccup and Toothless defeat the evil Alpha Bewilderbeast and Drago, Astrid teasingly pokes at his flight suit button and says that he found what he was searching for, making both of them laugh and Hiccup finally initiating a kiss with Astrid on the lips, pulling her close and gazing at her affectionately after they break apart from their embrace. Astrid later celebrates Hiccup's coronation as Chief of Berk and is seen by his side as the whole isle of Berk celebrates Hiccup's role as Chief. At the end of the sequel, Astrid is seen in the Dragon Races competing against the other Riders and Hiccup intervenes by taking the Black Sheep at the last second and throwing it into her basket for her.

An act that was seen performed by Snotlout and Fishlegs while they competed for Ruffnut's affection, so it shows that Hiccup simply stepped in to help out his lady against the other Riders as well. By the end of the film near the credits, Astrid and Stormfly are seen right next to Hiccup and Toothless as they stand on the pedestal overlooking the concluded games and Astrid's victory. He seems to make Astrid smile in the end no matter how many fights or misunderstandings they get in.

Friends/Allies[]

Toothless[]

I wouldn't kill him, because he looked as frightened as I was. I looked at him...and I saw myself.
―Hiccup, explaining to Astrid why he didn't kill Toothless.

Hiccup and Toothless have a brotherly relationship. The two of them do seem to see each other as equals, And everyone seems to acknowledge that Toothless is by far Hiccup's closest friend. At first, both keep their distance after Hiccup shoots Toothless down with the invention he called the "Mangler", but their mutual curiosity leads them to try and learn more about each other. Hiccup starts to observe Toothless and learns many secrets about dragons from these observations that help Hiccup advance in his dragon fighting classes. Toothless starts to trust Hiccup and even allows him to touch him, and eventually ride him. The depth of their relationship is furthered when Hiccup fashions a prosthetic tail for Toothless, only to discover that the two need each other to use it to fly; Hiccup is needed to manipulate the prosthetic tail while Toothless does the actual flying.

Toothless is later very playful around Hiccup, and is also very protective of and loyal to him. This is shown in how before, no matter how hard he tried, he couldn't get out of the cove without flying, until he heard Hiccup's scream, then manages to climb out and fight off a Monstrous Nightmare in the Dragon Training ring before it could kill Hiccup, and refusing to leave when the rest of the village joins in on the fight, seeing them as a threat. Later, when Hiccup is knocked off of him while attempting to escape the explosion that kills the Red Death, Toothless manages to reach for and protect Hiccup by wrapping him in his wings, even without his own prosthetic tail. Toothless is later overjoyed when Hiccup wakes up after the battle, jumping around his house with glee, and tickling him, before helping his human friend to walk on his new prosthetic leg.

Their friendship is also strong in Gift of the Night Fury when Hiccup crafted a new tail for Toothless so he can fly on his own. Toothless takes off, and only later Hiccup finds out why. When Toothless comes back, Hiccup finds out he took off to find his helmet. At the end Toothless trashed his new tail showing that he wanted to need Hiccup for him to fly.

Toothless and Hiccup's relationship remains mostly the same in Riders of Berk. They do occasionally have problems with one another as seen in The Terrible Twos and What Flies Beneath, but they always come through for one another. Hiccup and Toothless continue to grow closer throughout the series, and both of them risk their lives for each other multiple times. Hiccup tries to make Toothless happy by finding more Night Furies, but his efforts are foiled when Mildew and Alvin trap them both. In the end, Toothless remains happy to stay with Hiccup as his closest companion and to remain one of a kind. Toothless seems to be very happy and satisfied to be with Hiccup, and Hiccup is extremely grateful to have Toothless be the closest friend he could ever have. 

During How to Train Your Dragon 2, Hiccup and Toothless are shown to only have their friendship grown as they have become more reliant and love of each other like when Hiccup has an idea to confront Drago and try to convince him to stop trapping dragons, Toothless remains more friendly towards Eret and his crew. Though when Toothless is controlled by Drago through his Bewilderbeast and kills Stoick, Hiccup gets upset at the death of his father and blindly yells at Toothless to go away, which Toothless reluctantly follows shortly before being controlled again. Later, however, their friendship and loyalty to one another proves to be strong enough fully free Toothless from the Bewilderbeast's control. 

Later, after being set free, Toothless trusts Hiccup enough to be his eyes and ears and binds them so the Bewilderbeast can't control him. When they eventually get put to the ground, Toothless sits behind Hiccup when he talks to Drago one last time and that is when Drago tells his Bewilderbeast to kill Hiccup which Toothless quickly jumps in to cover Hiccup from the ice.

It is thought to be an unsuccessful attempt that kills both Hiccup and Toothless, but when a blue color and sound similar to when Toothless would shoot starts resonating from the ice, everyone wonders what was happening and then the ice breaks, revealing Toothless, who is now covered in a blue color, similar to his plasma bolts, on his back and in his mouth and nostrils, is covering Hiccup from the ice and then uncurls from Hiccup. When he uncurls, he sprints to the edge of an ice spike on Berk and challenges the Bewilderbeast under Drago's control to the dragon's role of Alpha to protect Hiccup. 

Hiccup and Toothless with their heads touching

A sweet moment

When Toothless, with his new found power and strength, attacks the Bewilderbeast, he proves that his love, friendship and companionship with Hiccup has only grown. Toothless celebrated his best friend's coronation along with Valka, Gobber, Astrid and the entire Isle of Berk.

Hiccup and Toothless also share the same roles in their respective societies. In the series, Hiccup was the de facto leader of the teens while Toothless was the de facto leader of the teens' dragons. In How to Train Your Dragon 2, Toothless ascends to be the Alpha and leader of all dragons while Hiccup becomes the Chief of Berk.

Gobber the Belch[]

Gobber is the blacksmith of the village, as well as a mentor, honorary uncle, and secondary father figure to Hiccup. Despite acting like all of his other students are expendable or simply paying little attention to their well-being, Gobber seems to have a soft spot for Hiccup. This is obscured, however, by the methods by which he goes about expressing his fondness of the boy. Though his intentions are good, Gobber often gives out comically bad advice that somehow just makes Hiccup feel worse. Most importantly, however, Gobber acts as the bridge of communication between Stoick and Hiccup, since the two seem to be unable to listen to one another otherwise. In fact, Gobber is the one who convinced Stoick to allow Hiccup to enroll in the Dragon Training classes, reminding the latter that he could not always hope to protect Hiccup; the best he could do was prepare him. At the end of the film, Gobber is the one who constructs a new prosthetic tail for Toothless and Hiccup's prosthetic leg. The other important role Gobber filled was training Hiccup in leather-working and as a blacksmith, which gave the imaginative teen an outlet for his mind along with practical design and fabrication skills. If an invention of Hiccup's fails, it's only because inexperience affected the design, never because of faulty parts, or that the parts were poorly crafted. Hiccup's innovation, improvement and engineering of his society's technology for his creations is often nothing short of sheer genius. At the end of How To Train Your Dragon 2 Gobber celebrated his coronation as Chief of Berk along with the other villagers.

Cloudjumper[]

Hiccup and Cloudjumper met each other when Hiccup was a baby. During the dragon raids on Berk, Cloudjumper broke into their house. His mother Valka saw this and tried to save him, but Cloudjumper was not harming him, in fact playing with him. However, he accidentally scratched Hiccup and attacked his father. As a result, Valka was taken by him, leaving Hiccup motherless for 20 years, while Valka on the other hand decided to stay with Cloudjumper fearing that she might harm Hiccup and Stoick or worse. Years later, they meet again along with his mother. Although they do not recognize each other, they do become close by their mutual love for Valka and Hiccup does not hold a grudge against him, At the end of the movie, Cloudjumper, along with the other dragons from the den celebrated Hiccup's coronation as Chief of Berk.

Snotlout Jorgenson[]

Hiccup and Snotlout are cousins in the books. Snotlout's big ego and bullying attitude makes Hiccup dislike him in the film. Snotlout openly mocks Hiccup's claims and is always boosting his own image by throwing mud on Hiccup's. When Hiccup becomes popular, Snotlout does join in and become a huge fan. Snotlout is willing to come and aid Hiccup in the battle with the Red Death, and he is actually the first Viking Hiccup teaches to bond with a dragon. Snotlout quickly wipes a tear in relief when he discovers that Hiccup is not dead, showing that he does care for him. Hiccup and Snotlout maintain a sort of rivalry ever afterwards. Snotlout recognizes Hiccup as the leader of the Dragon Academy and follows Hiccup's directions. While he may complain about specific details when not in battle once in a while, on the battlefield he will follow through with Hiccup's orders to the best of his ability. Though at times they work together, they are usually at odds. Hiccup highly dislikes Snotlout's arrogant attitude and stupid decisions, but he tolerates him, and at times the two do come together and accomplish difficult tasks. Still, there is a general feeling of dislike between both Hiccup and Snotlout. In Cast Out Part II, Hiccup acknowledged Snotlout's effort to try to save the Screaming Death's mother from Dagur. Hiccup "suspended the suspension" he earlier put Snotlout on and the two of them finally became friends in the end. At the end of How To Train Your Dragon 2 Snotlout celebrated his coronation as Chief of Berk along with the other villagers.

Fishlegs Ingerman[]

Hiccup gets along fairly well with Fishlegs throughout the franchise. In the books they are best friends, though they are much, much less close in the movie and series. Fishlegs does not seem to be as mean to Hiccup as the other teens during the first part of the film. He is not insulting or unkind, he just hardly speaks to him. After Hiccup becomes popular, Fishlegs, like the other teens, immediately begins to admire him. Hiccup is often happy to have Fishlegs around as a source of dragon information. Fishlegs, Hiccup, and Astrid seem to be the more sensible side of the gang. Hiccup often is kind and caring towards Fishlegs who is occasionally overly emotional. Fishlegs and Hiccup do not always get along well though. Often Fishlegs spurts out information in a very unhelpful or annoying way. Hiccup is often openly frustrated with him for doing this. Hiccup has been seen to even be slightly teasing towards Fishlegs when he is stuck in a tree and blames the crash on a flaming squirrel. Most of the time, Hiccup and Fishlegs do get along quite well, but Fishlegs is definitely not as close to Hiccup as Toothless or Astrid. At the end of How To Train Your Dragon 2 Fishlegs celebrated his coronation as Chief of Berk along with the other villagers.

Ruffnut and Tuffnut Thorston[]

Hiccup has a very basic relationship with the twins. In the beginning of the movie, they joined Snotlout on making fun of him. When Hiccup begins to excel at Dragon Training, they become big fans. Ruff even developed a (short-lived) crush on him. When Hiccup sets off to fight the Red Death, they help along with the others. The twins are relieved that Hiccup is alive after the battle. Hiccup does get annoyed by them with their love of fighting and destruction, but that does come in handy when needed. In IHiccup is willing to search all night to find them. He even trusts Tuff enough to gather information on what Alvin and Dagur are planning. At the end of How To Train Your Dragon 2 they celebrated his coronation as Chief of Berk along with the other villagers.

Eret[]

That was some pretty fine dragon wrangling back there. You'd make a good trapper.
―Eret's remarks to Hiccup at the end

Eret appeared in How To Train Your Dragon 2. Hiccup and Eret were initially in conflict as Eret attempted to trap dragons for Drago as opposed to Hiccup's respect for them. However, after Eret saw that he was wrong about dragons, he helped the Dragon Riders return to Berk to face Drago, with Hiccup suggesting that Eret take on Stoick's dragon, Skullcrusher following Stoick's death so that Skullcrusher will still have a rider recognizing that Eret can be trusted and become friends with him. Along with Valka, Gobber, Astrid and the rest of the village, Eret celebrated Hiccup's coronation as Chief of Berk.

Dagur the Deranged[]

Hiccup and Dagur have known each other for a long time, usually meeting with their tribes' treaty signing. Dagur often acts like a pesky older brother, using Hiccup as a knife throwing target or trying to drown him. Hiccup describes him as a "lunatic kid" and was not happy to learn he was the new Berserker Chief. Dagur confronted Hiccup about the Red Death and trained dragon rumors he heard about, only for Hiccup to deny them. The Dragon Trainers staged a dragon attack to save Barf and Belch, and the Berserkers retreated. Hiccup later met up with Dagur again in The Night and the Fury on Dragon Island. Dagur was happy to see Hiccup alive after the "attack" and kept going on about how he faced a Night Fury. Dagur then decides the two of them will hunt down the dragon together. He even starts calling Hiccup "brother," which he finds awkward. Dagur points out he and Hiccup are a lot alike: both are born leaders, sons of chiefs, and have fathers that had to be eliminated; the last one Hiccup quickly disagrees with. When Dagur learns that the truth about Berk's dragons, he feels betrayed and attacks Hiccup and Toothless. Hiccup beats Dagur, and he and he others head back to Berk, as they need to be ready when Dagur returns. After being defeated and telling the Berserker armada, Dagur tells them no one is to hurt Hiccup, except him, after he gets his dragon. Throughout the whole season, Dagur has constantly been trying to capture Hiccup and Toothless. Hiccup hated Dagur even more than he did before when he took his father, Stoick as hostage to trade for Toothless. In the end, Dagur was put in jail until he escaped three years later, and Dagur continued his quest for revenge on Hiccup and Toothless.

Despite Hiccup's own animosity for Dagur, he did not let Heather kill him when he found out the Berserker was her brother.

Hiccup's relationship with Dagur took a new turn after the first ordeal with Viggo Grimborn. In Enemy of My Enemy, he was surprised that Dagur was trying to help him and Toothless escape the Dragon Hunters, but he still didn't trust him. With no choice, Hiccup worked with Dagur to collect the ingredients needed to cure Toothless who had been hit by the Hunters arrows. When the potion caused Toothless to spasm and collapse, Hiccup attacked Dagur and even threatened to kill him. The two were soon captured by the Hunters, and while Dagur managed to escape he left Hiccup behind. This left Hiccup shouting that he hated the Berserker. However, Dagur came back with Toothless and save him. This left Hiccup wondering if Dagur really wanted to change.

Dagur showed up in Hiccup's hut asking him to teach him to ride a dragons he could find his sister. Hiccup agreed, hoping to get rid of him since Heather was on Dragon's Edge. Before that, he spoke to the Riders about the possibility Dagur was trying to change, though none of them were convinced, especially Heather. In Family on the Edge, Hiccup began to teach Dagur to ride a Gronckle, though it was still a trial. When the others found Dagur, Hiccup explained how Dagur had saved him. He admitted to Astrid he was still unsure about him, but Toothless let Dagur ride him. When Dagur found out about the Riders' plan to attack Viggo's fleet, he told them it was a trap. But the others' beliefs led Hiccup to trust his friends over Dagur and had him and his dragon locked up. Dagur managed to escape and proved it was a trap, which cost him his life.

After Dagur's supposed death, Hiccup felt guilty for not believing him.

Alvin the Treacherous[]

In the series, Alvin clearly has some sort of history with Hiccup's father, and recognizes Hiccup as "Stoick's little embarrassment" and "Stoick's little runt". Hiccup at first outsmarts Alvin into taking him to Dragon Island. It is there that Alvin realizes that Hiccup is a Master Dragon Trainer. Alvin then begins to try to train dragons of his own, but he fully realizes that to do so, he will need Hiccup. He abducts him several times throughout the series. Hiccup is usually sarcastic around Alvin which annoys the Outcast Chief considerably. This sarcasm displays an amount of contempt for the bloodthirsty Chief. Hiccup and Alvin both clearly underestimate each other. Hiccup was completely fooled by Alvin's plot to lure him to the Isle of Night, and Alvin has many times watched helplessly as the "90-pound boy repeatedly defeats an army of blood-thirsty savages." Alvin is Hiccup's main enemy in the television series, and he is one of the few characters that Hiccup has openly ordered Toothless to finish off. The animosity between the two of them has grown and grown as Hiccup has escaped Alvin and Alvin has nearly destroyed things that Hiccup cares deeply about. Alvin has notably targeted Astrid, and this has served to fuel the fire of the rivalry. Then Alvin discovered he could use Hiccup's love for Toothless to get at him, and this seemed to be the final straw. When Hiccup finally escaped, he and Toothless made a diving attack at Alvin and would have most likely killed him if they had not been downed by bolas. It is rare for Hiccup to be so determined to kill an enemy, but Alvin has given him good reasons to reach such decisions. In Defenders Of Berk, by the time of Cast Out Part I, Alvin claims that he is trying to change and helped Hiccup to defeat Dagur and rescue Stoick from Outcast Island in Cast Out Part II. Hiccup and Alvin become allies at the end of the season.

Mildew[]

Mildew and Hiccup are certainly not on any sort of good terms in the series. Mildew kicks off their rivalry by intentionally trying to get rid of the dragons. Mildew highly dislikes Hiccup because Hiccup has changed Berk, and because of this Mildew's animosity towards the dragons has stretched out to incorporate Hiccup as well. He intentionally makes Hiccup look as bad as possible in the eyes of the villagers and often attacks Hiccup's emotions through cruel guilt trips and accusations. This has lead to Hiccup highly disliking the old man. He never necessarily wishes harm upon the cantankerous old man, but when Mildew does get what is coming to him, Hiccup does seem to slightly enjoy it. Mildew tricks Hiccup into going into an Outcast trap, and this makes Hiccup even more angry with the old man. However, Hiccup does eventually pity Mildew when he sees him imprisoned, and Mildew convinces Hiccup to let him out of an Outcast cell. Hiccup is then fully willing to help the old man, and even tries to get him to bond with the dragons with some success. Unfortunately, it is all a trick, and Mildew winds up betraying Hiccup once again. Hiccup is unaware of this final betrayal, so he does try and rescue Mildew, but his father tells him that there is no way to help him. Hiccup currently does not necessarily like Mildew's company, but due his ignorance of Mildew's second betrayal, Hiccup has forgiven him. It appears in Worst in Show that Hiccup appears to know of Mildew's betrayal as he probably ordered Ruff and Tuff to send Butt and Head to head-butt Mildew. Hiccup also called Mildew a traitor in Cast Out Part II, further proving this point but in the end, Mildew helped Alvin save Hiccup, Toothless, and Stoick from Dagur and got the Berserkers off. It is possible Mildew has returned to Berk and became an ally.

Enemies[]

Drago Bludvist[]

You surely are hard to get rid of, I'll say that.
―Drago, to Hiccup.

Drago Bludvist is Hiccup's archenemy, and has an army of dragons and wants to rule the world, which means that this character will probably be the worst enemy Hiccup will ever meet. They are alike and different in many ways. Like Hiccup, he lost his left arm to a dragon, grew up fearing them but proved to have a talent for controlling them, and also possessed a great deal of mechanical inventive genius (as evidenced by his dragon traps). Unlike Hiccup, his fear transformed not into understanding but an obsessive need to dominate everything around him so he would never feel powerless again, and dragons were the ideal tool to do this with once he realized he could dominate them with sheer will and intimidation. The comparison goes further with their specific amputations and methods of how they each tame dragons. Hiccup lost his leg, and his method of taming a dragon involves calmly and peacefully placing his hand on the dragon's face. Drago on the other hand lost his arm, and his method involves shouting wildly and stepping cruelly upon on a dragon's head. In the end, Drago was defeated and Hiccup finally got his revenge on his father's true murderer.

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