Hiccup Horrendous Haddock III/Relationships

Stoick the Vast
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.

Though confused as to what to do about Hiccup's peculiarities as a Viking, Stoick is very protective of his son; 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 Green 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.

Toothless
Hiccup's relationship with Toothless is similar to that of the one between best friends or a pet owner and his or her beloved pet, perhaps even a sibling relationship. At first, both keep their distance after Hiccup shoots Toothless down with his bola sling invention, but their curiosity leads them to 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 fake tail for Toothless, only to discover that the two need each other to use it to fly; Hiccup is needed to manipulate the fake 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, perhaps seeing them as a threat. Later, when Hiccup is knocked off of him while attempting to escape the explosion that kills the Green Death, Toothless manages to reach for and protect Hiccup by wrapping him in his wings, even without his own fake 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.

Astrid Hofferson
Astrid is Hiccup's closest human friend and love interest in the film franchise. At first, she is unimpressed by his inability to stay focused, and often rebuffs his efforts to speak to her. Although she doesn't make fun of him like the other Viking teens, she appears to think him careless and irresponsible. Unlike her peers, Astrid doesn't fawn over Hiccup for his growing success in Dragon Training or for his popularity. Instead, she becomes jealous of him gaining the upper hand. After losing her victory to Hiccup, Astrid follows him into the forest for a final confrontation. She is furious with him but the moment she spots Toothless, her first instincts are to protect Hiccup. She tells him to make an escape while she intends to keep the Night Fury distracted. When Hiccup ends up revealing his friendship with Toothless, Astrid is appalled and runs off to tell on him, but is snatched off the ground midway.

After Hiccup convinces her to give him a chance to explain, Toothless takes her for a spin during which she holds on to Hiccup in fear until she apologizes and Toothless flattens out his wings. Once the flight turns more harmonious, Astrid is able to regard dragons from Hiccup's perspective and expand her mindset. She also grows a greater respect for Hiccup when he shows his adamancy in protecting Toothless, refusing to tell the other Vikings about their discovery of 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.

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 "M'lady"). 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. By the end of the third they were married and had two kids, Zephyr and Nuffink.

Gobber
Gobber is the blacksmith of the village, as well as a mentor 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 fake tail for Toothless and Hiccup's prosthetic leg.

Valka
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 with 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 sacrifice her happiness for the sake of his.