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This focuses on the relationships with the character Toothless.

Big FourEdit

AlliesEdit

Hiccup Horrendous Haddock IIIEdit

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http://www.fanpop.com/clubs/how-to-train-your-dragon/images/11265474/title/hiccup-toothless-fanart

Toothless is Hiccup's first friend and closest companion. Both depend upon one another to a great degree. Toothless is unable to fly without Hiccup, and Hiccup's lack of strength and traditional Viking skills, along with his prosthetic leg, are compensated for by Toothless' strength, speed, and power. The two of them have become extremely close, and their bond of friendship has survived many harsh trials. Both Toothless and Hiccup have made serious mistakes while dealing with each other. In the movie, Toothless has grown into his loyalty to Hiccup as he and the boy became more and more familiar with each other. Hiccup later allowed Toothless to fly again, and in doing so he would give the dragon back the thing he held most dear. As the movie progress, Toothless was willing to risk his own life to save his friend, protecting Hiccup from Hookfang and going as far as to dive his entire body into the exploding Red Death in order to save him.

In the fanfiction, authors still keep Hiccup and Toothless' unbreakable bond they share in the film and TV series, as it is an essential part of both of their characters.

Jack FrostEdit

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http://www.pinterest.com/pin/487022147176633531/

Jack and Toothless have little contact other than through Hiccup. The only thing the dragon and the winter spirit have in common is that they can both fly. Given Jack's mischevous and troublesome personality, Jack would take the longest (or at least the hardest) for Toothless to trust completely.

Merida DunBrochEdit

Toothless shares a light bond with Merida through Hiccup, and the fact that Merida has an affinity for animals through her own horse. In fanfiction, she is most commonly the one who rides Toothless behind Hiccup.

Rapunzel CoronaEdit

Toothless has interaction with Rapunzel, but not much. The closest interaction they have would be Rapunzel offering to heal Toothless' tail. With Rapunzel's open and innocent personality, it is likely for Toothless to trust Rapunzel quicker than he would Jack or Merida. Because of Rapunzel's personality towards animals, Toothless does like a few scratches or pats from her. Fans have made it to where their introduction is played for laughs, Rapunzel going into a "cuteness frenzy" over the dragon instead of the more appropriate, fearful reaction others would feel.

EnemiesEdit

Pitch BlackEdit

Toothless is a powerful creature, however when placed up against Pitch without Hiccup there is not much the Night Fury can do. Pitch's ability to move through shadow means that he can easily out-maneuver the grounded dragon. His control of the nightmare sand means that he could force Toothless to do battle with his Nightmares instead of him until the dragon had exhausted his firepower, and then Pitch would strike by either subjugating Toothless or simply killing him if he would not yield. Pitch wants Toothless for two reasons: 1) a magnificently powerful addition to the arsenal and 2) depriving the Big Four of their primary weapon.

Mother GothelEdit

Mother Gothel sees Toothless as a prize to be won. After all, a Night Fury would make a fine addition to the team. She however doesn't like to get her hands dirty as much so she lets Pitch take care of all the catching business.

Red DeathEdit

Originally, Toothless was in the service of the Red Death (retrieving food for it). When Toothless met Hiccup however, the two quickly bonded and Toothless showed Hiccup the Red Death. Hiccup and his friends then helped to defeat the Red Death, though at first it seemed like they were about to lose the battle.

Mor'duEdit

Without Hiccup, Toothless and Mor'du are actually quite evenly matched, strength-wise. Toothless's plasma blasts are all that the dragon can really rely upon against Mor'du as the Demon Bears' great strength allows him resistance to the Dragon's other attacks.

Extended UniversesEdit

Friends/AlliesEdit

Queen Elsa of ArendelleEdit

Having spent most of her life in her room, Elsa would have had plenty of time to read stories about dragons, both good and bad. However, upon seeing Toothless, a real dragon, she would initially be frightened of him, resulting in some sort of accident with her powers. Toothless however, upon seeing Elsa's kind and gentle personality, wouldn't be scared of her. Once she saw Toothless' gentle nature, Elsa's fear of him would subside, and she would become fascinated by him. If Elsa bonds with Hiccup, Toothless would eventually become comfortable enough to let her ride him.

Princess Anna of ArendelleEdit

Anna is someone who is not afraid to show her emotions. If she and Toothless were ever to meet, most likely on one of his adventures with Hiccup, Anna would be terrified of the the dragon, and would run behind a tree to hide from him. Once Toothless showed his more docile side however, she would be willing to approach him, and upon seeing how adorable he is, would start squealing in excitement about him. Toothless would in turn be somewhat annoyed with Anna, but if she manages to bond with Hiccup, he would be able to tolerate her and would gradually warm up to her. In time, he would be comfortable enough with Anna to let her ride him, if Hiccup allowed it.

Hiro HamadaEdit

BaymaxEdit

Mavis DraculaEdit

Dragons are found to be somewhat common amongst the monster community (one working the Hotel using its fire to heat the spa), so Mavis would be less likely to fear Toothless from the get-go.In other circumstances, Mavis would be a little scared of Toothless at first, but then, once she sees how he and Hiccup are together, her thoughts would definently change. Mavis would enjoy flying on Toothless. 

The Once-lerEdit

Mary KatherineEdit

NodEdit

Wreck-It RalphEdit

Vanellope von Schweetz Edit

EnemiesEdit

Prince Hans of the Southern IslesEdit

MandrakeEdit

King CandyEdit

YokaiEdit

OtherEdit

Friends/AlliesEdit

Stoick the VastEdit

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http://hollybell.deviantart.com/art/Toothless-and-Stoick-282567237

Toothless and Stoick get off to a really bad start from the moment they first meet. Stoick charges Toothless, seeing him as the ultimate threat to the island and the "Unholy Offspring of Lightning and Death itself". Toothless responds by singling Stoick out among all the other Vikings who are trying to capture him. He clearly sees Stoick as the greatest threat and he tackles him, thinking that Hiccup needs to be protected. Stoick struggles, but even with his massive strength he is unable to keep Toothless from pinning him to the ground. Toothless prepares to kill Stoick with a fire blast, but Hiccup screams "NO!" in utter despair and desperation. Toothless stops, and the Vikings quickly capture him. Stoick is outraged at Hiccup for training Toothless but soon discovers that the Night Fury can be used to find Dragon Island. He chains Toothless in a cruel harness and sails off with him as a guide. Toothless unwillingly leads the entire Viking fleet to the island, but they are attacked by the Red Death and soon the ship Toothless is chained to is set on fire. Stoick actually jumps into the water upon seeing that Hiccup was right about the dragon, and he tears Toothless free of the harness. After the battle, Stoick believes Hiccup to be dead. He apologizes to Toothless in painful grief, but Toothless reveals that Hiccup is still alive. Stoick deeply thanks the dragon for saving his son, and the two of them grow to have great respect for one another. In general, Toothless continues to respect Stoick as an authority figure. He allows Stoick to ride him during How to Pick Your Dragon even though it causes him great discomfort. Stoick does stand up for Toothless in When Lightning Strikes. Stoick's and Toothless' friendship is fairly strong, and it is made even stronger by their mutual love for Hiccup.

In How to Train Your Dragon 2, Stoick is killed by a mind controlled Toothless' plasma blast to the chest. Upon temporarily being freed from Drago's Bewilderbeast's control, Toothless comes to his senses, and approaches Stoick's body, gently nudging Stoick's hand sadly and in remorse for what he had done while under the Bewilderbeast's control, but redeemed himself for this incident by challenging and defeating the dark Bewilderbeast.

ThornadoEdit

Toothless and Thornado were enemies the first time they met. After Stoick was able to tame Thornado, they became friends. Thornado and Toothless worked together to fight Alvin and the Outcasts by combining their attacks to make them flee.

ValkaEdit

Toothless appears to like Valka, probably because she is close to his rider, Hiccup. Like Hiccup and Stoick, Toothless also wanted her to come back to Berk. Toothless plays with her and understands that she is Hiccup's mother. Valka and Toothless also share a mutual love for Hiccup.

CloudjumperEdit

In contrast to Toothless' more playful personality, Cloudjumper is more serious but can be playful sometimes. The two appear to become friends after learning about the relationship between their riders. Now being Alpha Dragon, Cloudjumper was the first to bow down showing his respects to 'Alpha' Toothless.

Gobber the BelchEdit

Gobber was the one who made Toothless' new tail-fin. The old Viking also understands Toothless, and dragons in general, which was seen in The Terrible Twos when he gave Hiccup advice about Toothless' odd behavior.

Astrid HoffersonEdit

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Toothless' first impression of Astrid is a very bad one. He sees her hurting Hiccup and decides she is a threat. He leaps towards her and prepares to land on her with mouth agape. Hiccup jumps in and pushes Astrid to safety and disarms her at the same time. He tries to calm Toothless down, the dragon barely able to control his rage. Astrid is introduced, but Toothless is not amused. Astrid then runs to try and tell Stoick, but Toothless and Hiccup abduct her. Hiccup convinces her to ride Toothless, claiming that there is nothing to be afraid of, but Toothless has other, less friendly ideas. He leaps into the air and pulls off an array of dangerous aerial maneuvers. Astrid is terrified into apologizing, and Toothless smooths out his flight. He then gives her an amazingly beautiful view of Berk from the air. She is amazed by the splendor of the scene and admits that Toothless is amazing. From that moment on, she helped Hiccup try and keep Toothless concealed. Toothless saved her from being eaten by the Red Death, and upon doing so gave her a big toothless smile. Astrid, like all the other Hooligans, is incredibly relieved to see that Toothless saved Hiccup. Toothless seems to have a good grasp on Hiccup's crush on Astrid, and he even teases Hiccup about it momentarily. Toothless continues to like Astrid, but her competitive nature occasionally annoys him. He is determined to stay on top of her and Stormfly, but the competition is friendly, and Toothless never seems to be uncomfortable around Astrid. He has gotten used to her violent "communication" methods and does not seem to mind her hitting Hiccup. He does openly wince at time when she punches, kicks, or arm-locks Hiccup. Still, as with Stoick, Valka and others, Toothless seems to greatly trust Astrid and appreciate her friendship and love towards his rider.

StormflyEdit

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In the books, Toothless has a huge crush on Stormfly, and often brags to her. Stormfly does not seem to care, but stays mostly by his side during How to Ride a Dragon's Storm. In How to Seize a Dragon's Jewel, Toothless blushes upon seeing Stormfly, telling her that he is "Toothless the Outcast", and points out the Wodensfang, telling her that his "sidekick, Wodensfang the Desperado."

In the movie and franchise, Toothless and Stormfly share a mysterious but pretty close friendship. They seem to enjoy each other's company, and occasionally they can be seen interacting with each other on friendly terms. Toothless seems to wish Stormfly farewell when she leaves in Gift of the Night Fury or she was telling Toothless to come with her. They are not always friendly, however. Often times Astrid's competitive nature can be seen in Stormfly, and that means that she and Toothless do occasionally get competitive. It is usually all in good fun, but sometimes the competitions can get a little out of hand, as when they were dragon boarding in Animal House. Toothless' friendship with Stormfly is probably aided significantly by the fact that Stormfly's rider is one of Hiccup's closest human friends. Not much is really known about their friendship, but it seems to be friendly and smooth, but a little competitive at times.

In How to Train Your Dragon 2, they are seen playing and talking to each other in a friendly manner, while Astrid and Hiccup are having a conversation. Their close bond is also hinted at when Toothless breaks free of the Alpha's control and calls the other dragons to aid him, with Stormfly being the first dragon shown to return to herself and join Toothless as he makes his stand. After the Bewilderbeast's defeat, Stormfly acknowledged Toothless as the new Alpha Dragon by bowing down to him.

Snotlout JorgensonEdit

Snotlout and Toothless dislike each other, though not as much as Snotlout does with Hiccup. However, such as in Defiant One they have been seen working together for a common goal, which was saving Hiccup from the Outcasts.

HookfangEdit

Hookfang and toothless by toffina-d7v9dtx

http://toffina.deviantart.com/art/Hookfang-and-Toothless-475769157

As far as can be guessed, Hookfang and Toothless met each other for the first time in the Dragon killing arena. Hookfang was attempting to kill Hiccup, and Toothless blasted into the arena in order to save his friend. Hookfang and Toothless engage in a short yet brutal fight. Hookfang backs down, but shoots Toothless an odd look of contempt. Ever since, Hookfang and Toothless have never really seemed to get along. They tolerate each other most of the time. Generally they simply avoid interaction. Occasionally they will get into fights, and when Hookfang went on a rampage, Toothless was quick to leap in and attack him. They share a sort of rivalry, and this is most clearly displayed in the Thawfest games. The dragons openly growl at one another before the games begin. Their relationship is not improved by the fact that Hookfang's rider, Snotlout, is often unkind to Hiccup. Toothless does not openly hate Hookfang, but there is very little evidence that either Hookfang or Toothless have any affection for one another. In How to Train Your Dragon 2, Hookfang acknowledged Toothless as the new Alpha Dragon by bowing down to him.

Ruffnut ThorstonEdit

Tuffnut ThorstonEdit

Barf and BelchEdit

Fishlegs IngermanEdit

MeatlugEdit

While Toothless doesn't interact with Meatlug a lot, she is a close friend. He stood next to her in Thawfest, along with Stormfly. In Worst in Show, Toothless tries to comfort Meatlug when she was sad about Fishlegs spending time with Iggy. He even looked back at her when he left with Hiccup, showing concern. Near the end of How to Train Your Dragon 2, Meatlug acknowledged Toothless as the new Alpha dragon by bowing down to him.

EretEdit

Toothless' relationship with Eret, son of Eret is very similar initially to Hiccup's. While Eret did originally try to capture Toothless and give him to Drago for his dragon army, they eventually become allies, and while Eret never rides Toothless, like many other former and current villains have done, they are shown to trust each other at the end of the film, even if their relationship only goes to 'acquaintance' level.Toothless, however is shown to be quite relaxed in the company of Eret when Hiccup surrendered to him, and whether this is due to the fact that Toothless trusts that Hiccup has it under control, or whether he sees Eret as less of a threat, or perhaps sees his potential for improvement, he does definitely show his carefree side around Eret more along with many other characters.

EnemiesEdit

Unnamed Whispering DeathEdit

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http://taipu556.deviantart.com/art/Toothless-vs-the-Whispering-Death-370806569

Toothless' arch rival is a Whispering Death from his past. Both he and this dragon have some sort of serious history, and are willing to fight to the death over the grudge. What the events were that started the feud are unsure, but the Whispering Death has a large bite mark from his previous battle with Toothless. This Whispering Death shows up in Berk looking for Toothless and discovers that his old rival is unable to fly, which he uses to his advantage. The Whispering Death refuses to be trained by Hiccup and nearly eats the boy. Toothless is nearly killed when the Whispering Death attempts to blast him off of a cliff. Hiccup arrives just in time, and he and Toothless must work together to defeat this powerful enemy. Toothless had originally wanted to settle the score on his own, but Hiccup eventually convinced him to accept help. Whatever started the grudge was certainly serious. Toothless is so set on seeing the fight through that he actually fires a plasma bolt in front of Hiccup to get the boy to stop following him. Hiccup is deeply saddened by this, and Toothless realizes this, but he is still willing to hurt Hiccup's feelings for the sake of dealing with this past rivalry. Toothless cares for Hiccup deeply, so the fact that he would risk harming their friendship for the sake of revenge gives a tiny glimpse at the seriousness of his animosity towards this Whispering Death. In the end, Toothless spares the Whispering Death after defeating him. The Whispering Death then quickly retreats, and Hiccup is proud of Toothless for sparing his foe that had only moments before nearly killed them both. It is possible that they are no longer foes and consider the matter to be closed. Toothless' experience with this dragon made him aggressive toward other Whispering Deaths.

Dagur the DerangedEdit

Toothless shows more of his ferocious side whenever he sees Dagur, since he is obsessed with killing dragons.

Drago BludvistEdit

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http://www.deviantart.com/art/Bewildered-Toothless-creepy-warning-491035654

Like all antagonists, Toothless has a deep hatred for the self-proclaimed "Dragon God." Drago used Toothless, by the Bewilderbeast's control, to attack Hiccup, but ultimately killed Stoick instead. Drago rode Toothless to Berk until Hiccup freed his dragon partner and they defeated the mad man together.

Like other dragons, Toothless fell victim of the Alpha's hypnotic abilities and was forced to attack Hiccup, but ultimately killed Stoick instead. When broken free and the large Dragon attacked Hiccup directly, Toothless used his body to shield him from the icy blast. Toothless then challenged the Alpha and defeated him by having the other dragons join him and destroyed his left tusk, becoming the new Alpha and redeeming himself for his unintentional hand in Stoick's demise under the Alpha's control and thus gaining his innocence back.

OtherEdit

Alvin the TreacherousEdit

In the books, Toothless never liked Alvin. He believed the man was an Outcast, which was later proven true. In the series, Toothless doesn't hold back when facing the Outcast leader. He was shown to remember how Alvin kidnapped Hiccup back in Alvin & the Outcasts when he saw him again in Heather Report Part II. In We Are Family Part II, Toothless and Hiccup charged at Alvin, and might have killed him if they hadn't been tied up. In Cast Out Part II, Toothless was not thrilled about having Alvin join him and Hiccup to save Stoick. He even smacked him with his wings when Alvin was joking about his death grips. Toothless did seem pleased as he and Hiccup watched Stoick and Alvin make up though, probably gaining slight trust in him.

The Screaming DeathEdit

In Tunnel Vision, Toothless met a new enemy: the Screaming Death. This large Dragon goes after him and Hiccup more than the other Dragons, most likely due to Toothless attacking the Screaming Death more often. Hiccup and Toothless were able to lure the albino Dragon into colliding with a sea stack, and injuring its wing. The Screaming Death obviously remembered this when they met again in Appetite for Destruction, as Hiccup and Toothless were its main targets other than sinking the islands. In Cast Out Part II, Toothless is happy to see the Screaming Death reunite with it mother.

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