Astrid and Hiccup's Relationship

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Astrid and Hiccup's relationship throughout most of the franchise would best be termed as not always platonic best friends.

Astrid's feelings for Hiccup usually manifest themselves as extreme devotion and protectiveness, as she is always the first to aid him in any situation and the last to leave him, which Hiccup reciprocates towards Astrid, she was the last to leave him on his serch for new dragons before Dagur broke out of prison and they moved to the edge. It appears to be an unspoken assumption that Astrid will accompany Hiccup on his adventures, more so then the other Vikings, and will usually invite herself along regardless. On the rare occasions that they are separated by mitigating circumstances, she is shown to worry greatly about him and is always overjoyed to be reunited with him. Beyond the romantic elements of their relationship, Astrid and Hiccup are the closest human friends that either has.

How to Train Your Dragon
At first, Astrid is shown to be disinterested in Hiccup - due to her thinking he is not like the other Vikings. However, whilst the other Vikings actively ridicule Hiccup, Astrid seems more suspicious towards him, but does give him a very small look of pity behind his back as his father drags him to the house, only to become angry with him due to his incompetence in the Arena. Her dislike for him grows into jealously when he becomes more skilled at 'fighting' dragons than she is, throwing a fit when he is labeled the Viking to kill the dragon in the Arena. Afterwards she goes to the Cove to learn his secret. When he tries to get her to take him to the village since she still hasn't spotted Toothless, she twists his arm back and then kicks him to the ground and drops the head of her axe into his groin. Once spotting Toothless, she had an instinct to protect Hiccup, pulling him to the ground and trying to get him to run while she challenged Toothless, until Hiccup pulled her down and tried to explain. Although it is unknown if she was actually running to the village, Astrid runs away in shock and fear, only to be picked up by Toothless and put in a tree. After finally agreeing with Hiccup to "let him show her" why he has a dragon, (having no choice other than fall out of the tree and die) she reluctantly gets on the dragon. But thanks to her attitude, Toothless doesn't listen to Hiccup's words to get down, slowly. Instead racing down, dunking into the water, and spinning in circles until Astrid apologizes. After he slows down, Astrid admires the beauty of the sky, especially as the sun starts to go down. She waves her hand through the clouds and even falls back so she can feel it in her hair. As they approach Berk, Astrid puts her arms around Hiccup's waist and leans her head on his shoulder, to Hiccup's surprise and then delight. As they go back into the air, she admits flying is amazing, and adding onto to it by saying Toothless is amazing. As they try to go back, Toothless suddenly hears a call and flies into line with a ton of other dragons, telling Astrid to get down so they aren't spotted. Once they are in the Dragon's Nest, Hiccup urges Toothless to get out for his and Astrid's safety, both Hiccup and Astrid slightly frightened when a Gronckle fails to get enough food for the Red Death and is promptly eaten. Once escaping the Nest, Astrid excitedly tells Hiccup they have to tell Stoick, but Hiccup gently takes her arm, telling her that they'll kill Toothless if the village finds out. She asks if he's really being serious about wanting to keep the Dragon's Nest a secret, something Vikings have searched for for thousands of years just to protect his pet dragon. When Hiccup firmly says yes, her face changes, realizing just how important Toothless is to him. She decides to support him, asking what he's going to do, to which he says he'll think of something. She then punches him in the arm, saying that for kidnapping her. As he rubs his arm, she grabs him by the shirt and quickly kisses his cheek, stuttering slightly as she says that was for everything else before running back home. In the Arena the next day, she meets with him before he goes inside, gently asking what his plan is. He tells her he has to try to stop this, but if something goes wrong then to take care of Toothless. She accepts, before asking him to promise her nothing will go wrong. He doesn't get the time to respond, as Gobber tells him it's time. After trying to train the Monstrous Nightmare and Stoick angering it by ringing against the cage, Astrid cries out for Hiccup, using her axe to force the arena open and then throwing a hammer at the dragon to distract it from Hiccup, running away from it herself. After Toothless is locked up on a ship heading towards the Dragon's Nest, Hiccup is angry and saddened, and Astrid doesn't make him feel better when she states the obvious (he's lost his tribe, father, and best friend) but slowly turns it into an almost pep talk/motivational speech. She asks him what he plans to do and he responds with "I don't know, probably something stupid" when she tells him it's a good start but he's already done that, he responds with something crazy. When Hiccup introduces the dragons in the arena to the other Viking teens, she shows her support, (probably being the main reason they go in the first place) and when Ruffnut tries to flirt with Hiccup, Astrid pulls her away by her helmet. During the battle against the Red Death, Hiccup saves Astrid when the Red Death tries to suck Stormfly into her mouth and eat her, before Hiccup has Toothless shoot a plasma blast at the Red Death, Astrid falling to the ground before Toothless grabs her. She smiles up at Toothless and Hiccup before being placed on the ground. After Hiccup disappears in the smoke and fire, Astrid rushes to the scene, believing Hiccup is dead. Tears come to her eyes, and when she sees Hiccup again even more tears come to her eyes as she rejoices with the Vikings. After he wakes up and goes outside she sneaks up behind him and punches his back, claiming that was for scaring her. As Hiccup protests angrily, she smiles and pulls him forward for a real kiss on the lips. He quickly tells her he can get used to it as she blushes. She then joins Hiccup and the other teens for a dragon ride on their dragons as the movie ends, concluding their relationship as not always platonic best friends.

It is possible that Astrid had feelings for Hiccup before the events in the movie, due to her immediate change in behavior during the first flight. She might have just ignored this since Hiccup didn't meet the usual Viking standards. When Hiccup was thought to be dead after he defeated the Red Death, Astrid is the only Viking to be brought to tears, meaning she took it the hardest, besides Stoick.

Gift of the Night Fury
Astrid remains a close friend of Hiccup in Gift of the Night Fury, as Astrid and Hiccup both advocate the idea to make up new holiday traditions to cheer the tribe up, and they discuss the prosthetic Hiccup makes for Toothless so the Night Fury can fly on his own. He also calls her "M'lady" we she hands him a cup of Yak-nog. It's never officially confirmed if they've become a couple. Even so, near the end of the special, Astrid comforts Hiccup when he's missing Toothless, and even kisses him on the lips and hugs him. She still likes to tease Hiccup however, as she did with him when she noticed Toothless had entered the Great Hall, before she giddily turned him around so he could see Toothless was back.

Riders of Berk
In the Riders of Berk series they appear to have a budding relationship, but they are quite shy and awkward about it. Their romantic attachment is more suggested in their dynamic and interaction then outright stated. Whilst Astrid maintains more of her initial stern, authoritative demeanor with the other Vikings, she opens up more when alone with Hiccup, and apparently feels safe showing a considerably softer, more whimsical side of her personality to him. The two are incredibly close, with Astrid acting as Hiccup's confidant when he needs advice on personal problems, and often pair off from the others when needing to achieve something especially difficult.

How to Start a Dragon Academy
When Hiccup and Toothless win the best trick contest ,Astrid says "''He's still the best"! ''

Animal House
After Hiccup and Astrid run into an avalanche while riding their dragons, Hiccup attempts to protect her, but they both fall into the huge heap of snow and ice. Their dragons use their firepower to open a hole in the ice so they don't freeze and suddenly realize that they're holding each other, both backing off and blushing.

Later, after Hiccup and Astrid tell Fishlegs what happened, he suggested they could have used each others body heat, to which they scoot away from each other and blush.

Portrait of Hiccup as a Buff Young Man
Hiccup at the beginning was busy complaining to Gobber and Stoick about his painting as a buff man, Tuffnut asks "Whoa, what happened to Hiccup?" Then Astrid replies "Who cares" in an aroused way.

Later, during the cave-in, Astrid refused to leave Hiccup (who fell into a pitfall) until Fishlegs pointed out that there won't be anybody to leave Hiccup if they all got trapped.

Thawfest
She did say in Thawfest that one thing she "always liked about Hiccup" is that he was a gracious loser, further supporting the theory that Astrid had feelings for Hiccup prior to the first movie.

She is also in a sense Hiccup's moral guide, keeping him honest. At the end of the episode she kisses him for being himself.

When Lightning Strikes
In When Lightning Strikes, Astrid is the first person that Hiccup seeks out before leaving the island, and when Hiccup tells Astrid that he is leaving with Toothless the first thing that she asks if he will come back. Despite his assurance that he will return when the villagers all realize that the lightning wasn't because of Toothless, Astrid appears sad and distraught.

Fright of Passage
In the beginning when Astrid wants to go after the flightmare, hiccup tries to stop her. She says "Come on hiccup don't tell me you haven't been dreaming about the flightmare, going after it, learning about it, training it." Then hiccup says "Well you know Astrid training dragons isn't the only thing I think about." She then asks him "Are you actually saying that to me with a straight face?" This might suggest that Astrid and Hiccup are thinking about each other more intently.

A View to a Skrill Part I & A View to a Skrill Part II
These episodes continue the trend of Hiccup and Astrid choosing to be close to each other and the pair showing more concern for each other than typical of the others.

Astrid joins Hiccup, and this time Snoutlout, on the mission to find the overdue Bucket and Mulch, after rescuing the missing Vikings from Berserkers it is Astrid and Hiccup alone who speak to the pair. Once the frozen Skrill is returned to Berk, Astrid and Hiccup stand right next to each other with Snoutlout and Fishlegs on either side of the pair. When Hiccup goes to tell his father about the Skrill Astrid accompanies him and Toothless. While speaking to Silent Sven Astrid stands next to Hiccup, with Snotlout and Fishlegs on the other side. Although, when they land on the seastack after the Berserker attack, they place Fishlegs between their dragons when they land, this could be due to their secondary positions in the V-formation with Fishlegs in the lead. Then when the two teams reunite Hiccup takes up a position right next to Astrid in the formation.

When the Skrill first prepares to fire on Hiccup and Toothless, it is Astrid that cries out his name and rushes forward to help before the others follow. Then when Hiccup and Toothless dodge and the Skrill fires on the group, it is Astrid’s name that Hiccup cries in alarm, despite the fact that the entire groups was fired upon. In contrast, when the Skrill actually hits Snotlout neither Hiccup nor Astrid show much concern, Astrid actually seems to be deriving pleasure from it.

Astrid also acts as Hiccup’s voice of reason and devil’s advocate for his plans. When Hiccup states that he will follow the Skrill into the clouds by using Toothless’ ability to echolocate Astrid asks if that even works in the clouds. Also, when Hiccup places Astrid in charge of the team attacking the boats and he takes Tuff and Ruff to fight the Skrill Astrid points out that he needs to be careful because he has more metal than the others.

Frozen
She hugged Hiccup in front of Gobber when he returned from rescuing Johann in Frozen

The Eel Effect
Astrid was willing to wait outside in the cold while she was suffering from Eel Pox for Hiccup to come back and was very happy to see him return in The Eel Effect. These actions suggest that her crush on him is getting harder to hide.

Race to the Edge
Despite there being no direct confirmation, in Race to the Edge, that Hiccup and Astrid are a couple, their relationship is shown to be closer and stronger. It is almost like they both have feelings with each other, and both know the other has feelings for the other, but both feel that there are things more important than a relationship at the moment. However, when they are alone together or one of them is in great danger, they aren't afraid to show a little affection.

Dragon Eye of the Beholder Part I & Dragon Eye of the Beholder Part II
Hiccup appeared upset that Astrid mentioned that she's done searching for new dragons and joining the Berk guard, despite saying how happy he was for her. Astrid then advised him to start thinking about what's next for him and Toothless.

Hiccup also dives down to save Astrid after she falls into giant eel infested waters.

Then while Hiccup is exploring the Reaper, the Dragon Riders are captured by Dagur and locked in a cage on the Reaper. When Hiccup meets Dagur again after three years, Astrid is one he cries out for.

Imperfect Harmony
After they land on Melody Island, Hiccup and Astrid spend most of the time together even slept next to each other. When the Death Song was about to shoot at Hiccup, Astrid push him away and the amber immobilizes her.

When Darkness Falls
In When Darkness Falls there are several instances which point to the complex relationship that has develop between the two to this point and establishes a theme that carries through the entire series. When they first land on Dragon's Edge and Hiccup takes charge of having them set up the camp Snotlout complains about liking "whiney Berk Hiccup" more than "Princess outpost Hiccup" to which Astrid replies, "I know, right?" before giving Hiccup a secret double thumbs up. Then the next day when everyone is pushing their ideas for the outpost Astrid smiles when Hiccup states that they need one idea, as if she fully expects Hiccup to choose her design and then gets upset when Hiccup states that everyone else's ideas are good. However, what is perhaps the most telling is the layout that Hiccup chooses for Dragon's Edge. Hiccup placed his hut right next to Astrid's hut and they are closer together than any of the other huts.

Reign of Fireworms
When Astrid is "locked up" Hiccup ask her "So, what are you in for?" to which she replies "Not funny!" and when Hiccup is "locked up" she ask him the same thing. That means that they like to make fun about each other.

Have Dragon Will Travel Part I & Have Dragon Will Travel Part II
In Have Dragon Will Travel Part II, Heather asks Astrid if she and Hiccup are a couple. First, Astrid panics and throws her axe into the top of a tree. Then she adamantly states the two are just friends, though appears a little nervous on the matter, and it is clear that Heather doesn't buy her denials. Also, when Heather states that Hiccup is kind of cute Astrid blushes, smiles and says, "I guess. If you like that unassuming, heroic, dragon rider type." Then at the end, Hiccup feels sorry for Astrid losing a friend, knowing the two got really close. Astrid then puts her arm around Hiccup and states, "But I still have you."

The Next Big Sting
The Next Big Sting

Astrid's Team
After an attack on Berk, Astrid finds out that her parents house got destroyed during the attack. Fortunately, her parents out when the attack was taking place. Astrid tells Hiccup that she will be staying in the arena and Hiccup said that he's staying there too, due to his dad's loud snoring.

Night of the Hunters Part I & Part II
At the beginning of the episode, Hiccup is worried that Astrid has been gone all day without telling anyone where she's gone. Feeling that something's wrong, he decides to lead the others on a search party to find her. Hiccup sees her as she begins to sink into the ocean and immediately dives to save her. As he pulls her out of the water he shouts her name, fearing the worst. After a few seconds she weakly regains consciousness and asks "What took you so long?" Hiccup then holds her in a tight hug thanking the gods she's alright, his panic still evident.

Snow Way Out
Somewhere in the middle of the episode, Astrid tells Heather that she is worried about not telling Hiccup, explaining to Heather that she knew Hiccup trusted her. While Heather reassures Astrid that this is fine, Astrid still looks doubtful. A little after this event, Hiccup tells Astrid that he relies on her. Astrid looks taken aback by that, remembering her talk with Heather. At the end, Hiccup is upset when Astrid tells him that Heather was helping them, since he is surprised that Astrid was keeping a secret from him that could help them majorly. This is also because Hiccup entrusts everything to Astrid, even things that he doesn't tell his dad, and this was a huge act of betrayal. Astrid was scared during this account, because Hiccup was being unusually cold to her. At the end, it seems like they reconcile.

Edge of Disaster Part I & II
When Hiccup prepares to leave, Astrid implore him to not leave her alone but in the end she accepts to stay on the Edge. Later in the episode she says "Hiccup, where are you when I need you?". When Hiccup finally arrives, she is so happy that she even punches Dagur when he said he hated Hiccup.

Enemy of My Enemy
At the beginning, she confront him because he wanted to go on a patrol alone.

Buffalord Soldier
In the episode Buffalord Soldier, Astrid became deadly ill with a disease called "The Scourge of Odin" and even before he knew she was sick, Hiccup was very concerned, but much worse when Stormfly was acting panicked. He paced around the floor as Fishlegs searched for a cure, and caught Astrid before she fell to the ground, concern etched in his face. While bringing her to the Buffalord she fell of Stormfly he caught  her and shushed her softly, held her hand, and begged her to stay alive a little longer, for him, confessing he couln't imagine a world without her (the most romantic thing he's said so far in the show) before starting to panic when the clear Buffalord saliva did not cure her. When Viggo arrived to take the dragon, Hiccup begged him to let them have the cure, claiming he would not leave without it, showing he will do anything to save Astrid's life. Finally getting the green solution, he urged her to drink, before helping her up as color came to her face. After the Viking funeral for the fishing boat where she got sick, Astrid thanks him for saving her, which he tells her that she would have done the same for him, before she too confesses she couldn't imagine a life without him, both smiling.

A Grim Retreat
Astrid is the one who convinced Hiccup to go on an island to relax. At the campfire, they stay together. When Toothless and Hiccup go into the water she says "come on, come on" showing she cares for his saftey.

To Heather of Not to Heather
When Astrid and Heather are talking Heather mechanise Hiccup Astrid smiles and look to the ground Heather tells her to to express her feelings.

Stryke Out
When Snotlout accidenly gets Hiccup and Toothless captured and taken to dragon fights Astrid was very worried and when she found him she ran to him and hugged him while they were flying out she said she was glad to have him back and she was worried, Snotlout said he wasn't worried Fishlegs said that would've killed him if they hadn't Hiccup.

Last Auction Heroes
When the riders were captured, Astrid put her hand on Hiccup's shoulder and he looked at her and put his hand on her's. Later in the episode, when Hiccup was drowning, Astrid and Stormfly caught him.

Defenders of the Wing, Part 1
When Hiccup tried to train the Speed Stingers, Astrid tried to help him but was stopped when Mala blocked her path with her sword and then Throk held her back.

How to Train Your Dragon 2
By the time of the sequel, Astrid and Hiccup are an official couple, boyfriend/girlfriend or possibly betrothed. She even teases him in an affectionate manner, and calls him babe when they are fighting Drago's army. They are comfortable sitting very close to each other, as opposed to in Animal House when they nervously moved away from each other. They are even so close that Astrid casually braids Hiccup's hair. Astrid also helps Hiccup in personal problems he can't figure out on his own. Also, she has displayed greater loyalty, trust and protectiveness towards Hiccup, just like Valka throughout the movie. They exchange two cheek kisses and a big kiss on the lips at the end.

Trivia

 * In the song, "Fly Dragons Fly," which aired on Cartoon Network, a part in the lyrics said, "Astrid and Hiccup, each other they like. Wonder if they marry? They might."
 * In the 2nd movie this is the first time Hiccup kissed Astrid instead of the other way around.
 * Astrid and Hiccup have kissed on the lips 4 times.
 * Hiccup liked Astrid before Astrid liked him.
 * Astrid always screams "Hiccup!" when something happens to him and Hiccup always screams "Astrid!" when she in danger.
 * Snotlout tells Hiccup that he can "have" Astrid because he likes Heather. Hiccup laughs and thanks him, acting like he already KNOWS who Astrid has chosen.
 * At the end of HTTYD 2 just as Astrid and Stormfly are about to catch the black sheep Hiccup and Toothless grab it in at the last few seconds and puts it in Astrid's sheep pile instead of his own. This is similar to what Fishlegs and Snotlout did for Ruffnut at the beginning of the movie.