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.

Hiccup has always liked Astrid from the beginning. However, his awkwardness lands him in a more passive position in most of the development of their relationship. 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 search 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 than 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 of them has.

How to Train Your Dragon
At first, Astrid appears to be disinterested in Hiccup. She considers him irresponsible when he tries to go against higher orders to prove himself and is particularly unimpressed with his inability to stay focused in the training arena. Unlike the rest of her peers, Astrid never ridicules Hiccup or laughs at him but as he walked past the other teens, she stopped sharpening her axe to stare at him with curiosity.

Her vendetta against him seems to be on more personal ground and is fueled by suspicion and jealousy. Astrid grows particularly annoyed with him when he takes the upper hand during 'dragon training', suddenly showing far superior skills than she could ever hope to achieve despite all her hard work and determination. She also seems to be the only one able to see through the facade Hiccup puts up in the wake of his popularity. By the time Hiccup takes the final win, Astrid has grown beyond aggravated.

Instead of confronting him calmly like she initially did when questioning him about his weirdness, Astrid follows him to the Cove and aggressively tries to press the truth out of him. When she hears something she throws Hiccup to the ground and moves forward to investigate. Once she spots Toothless, however, her feud with Hiccup is forgotten and her first instincts are to protect him from the dragon. Notably, it's not the first time Astrid warns Hiccup as she told him to get down and out of sight when facing danger during their training sessions. This time around, however, she physically attempts to protect him by pulling him to the ground with her and then telling him to run while she distracts Toothless. Hiccup is quick to intervene before anything serious happens. He attempts to calm both parties down and explain himself to Astrid, who is thoroughly astonished by the revelation. 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 dropped 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 to her death) she reluctantly gets on the dragon. But sensing her attitude, Toothless doesn't listen to Hiccup's instructions to get down gently. Instead he races down, dunking his riders into the water, and spinning in circles. Astrid wraps both her arms and legs around Hiccup in fear, indicating she must have some trust in him. Astrid apologizes, and Toothless slows down, and she 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, Hiccup 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. In horror, Astrid wraps her arms tightly setting Hiccup's chest. Once escaping the Nest, Astrid excitedly tells Hiccup they have to tell Stoick, but Hiccup gently takes her arm, telling her no, 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, as it's something Vikings have searched for since they first arrived, just to protect his pet dragon. When Hiccup firmly says yes, her face changes and shoulders drop, 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 by the next morning. She then punches him in the arm, saying that's for kidnapping her. As he rubs his sore 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. Leaving Hiccup in shock and confusion.

In the Arena the next day, she meets with him before he goes inside, gently asking what his plan is. He says he has to try to stop this, but if something goes wrong he asks her 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 to go in. After trying to train the Monstrous Nightmare and Stoick angering it by losing his temper, Astrid cries out for Hiccup, using a nearby axe to force the arena door open and then throwing a hammer at the dragon to distract it from Hiccup. She continues trying to distract the dragon so Hiccup can get away until Stoick enters the arena and Toothless is subdued. Astrid then holds Hiccup back as he's desperately trying to stop his father and the other Vikings from chaining Toothless up.

After Toothless is locked up on a ship heading towards the Dragon's Nest, Hiccup watches them sail off in despair, 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 why he didn't go through with his plan to kill Toothless when he found him in the woods, and he eventually confides in her that he saw himself when he looked at him. 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 "then something crazy".

When Hiccup introduces the dragons in the arena to the other Viking teens, she shows her support (probably being the main reason the other teens go in the first place), and when Ruffnut tries to flirt with Hiccup, Astrid pulls her away by her helmet. She makes sure the other teens are supportive as well.

During the battle against the Red Death, Hiccup and Astrid both ride Stormfly, Hiccup finding his confidence and calling out instructions to the other teens. He leaves her to fly the Dragon alone when he jumps down to free Toothless from a burning ship. He later saves Astrid when the Red Death tries to suck Stormfly into it's mouth and swallow her, before Hiccup has Toothless shoot a plasma blast at the Red Death, Astrid starts to fall to the ground before Toothless grabs her. She smiles up at Toothless and Hiccup before Toothless gently drops her on the ground. There she, Stoick, and the other Vikings watch in horror and awe as Hiccup and Toothless fight the Red Death in the clouds above. 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 hears Stoick proclaim that he's still alive, 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 the punches 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 them 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.

Legend of the Boneknapper Dragon
When Hiccup was upset for Gobber Astrid took a few steps closer to him perhaps to comfort him. When the they were on the boat Hiccup and Astrid sat next to each other, and while they were stranded on the island they are often standing next to each other. At Gobber's outrageous stories, and all the teens' annoyance at them, Astrid shoves Hiccup in Gobber's direction as a hint that he put a stop to this, indicating that Astrid trusts Hiccup to bring some sense to their situation.

Book of Dragons
Astrid and Hiccup are sharing a bench at a table in the Great Hall, and sitting very close together.

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. She gestures for some support in her ideas, and he's quick to give it. When the other teens didn't like her Yak-nog, she says she bets that Hiccup would like it as she runs off to share it with him. As 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, holding his hand, lifting his face by the chin to look at her, and then kisses him on the lips, followed by a sincere hug. He's shocked again, but quickly relaxes as he rhetorically asks her where Toothless went. 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.

Dawn of the Dragon Racers
When Snotlout wins Astrid tells Hiccup "One out of two ain't bad, and for what it's worth I always knew red was your color". Hiccup responds "Aw Astrid thank you." After which Astrid jokes "I was talking to to Toothless." In the flash back, when Hiccup was trying to get the other riders not to have a dragon race, Astrid was the one he asked to back him up. She did at first, but when he saw the other riders racing including Astrid, he yelled to her, "Really Astrid?! Where's the love for the acting chief?". When Snotlout crashed into Astrid and she fell off of her dragon, Hiccup was worried and upset about her breaking her arm. In preventing her from injuring herself more, he refuses to allow her to race after that.

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"! Hiccup was given responsibility of keeping the dragons out of trouble he got so beat up from running from crisis to crisis putting flaming sheep out Astrid went to see him, before she went in his room he said to Toothless "Astrid, perfect I don't look to beat up do I ?", which indicates that Hiccup cares what Astrid thinks of him.

Animal House
After Hiccup and Astrid get swept up into an avalanche while riding their dragons, Hiccup attempts to protect her, but they both fall into the huge crevice of snow and ice. In the dark, they call for each other, and Astrid tells him she's freezing. So he tells her to "come here". Their dragons use their firepower to open a hole in the ice so they don't freeze and in the light they suddenly realize that they're holding each other tightly. They both back off awkwardly, assure the other that they're ok, and Astrid teasingly punches his arm again.

Later, Hiccup and Astrid are sitting next to each other while they tell Fishlegs what happened, and he suggested they could have used each others body heat to stay warm, to which they scoot away from each other and blush.

In Dragons We Trust
After dropping their dragons off at Dragon Island, Astrid leans against the ship's mast, and Hiccup quite obviously changes his position to lean against the mast in the same fashion. He then confides in her his suspicions that Mildew framed the dragons for the recent mishaps at home.

Alvin & the Outcasts
Hiccup was hiding as not to get captured, until Alvin got a hold of Astrid. It was then that Hiccup showed himself and made a deal with him to leave the people of Berk in peace if he proved he was the Dragon Conquer.

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 frantically refused to leave Hiccup (who fell into a pitfall) until Fishlegs pointed out that there won't be anybody to save Hiccup if they all got trapped. She and Fishlegs were the teens most fervently trying to dig Hiccup out once they were back outside.

Heather Report, Part 1 & Part 2
Though she insists she's not, it's quite clear that Astrid is dealing with feelings of jealously when Hiccup starts neglecting his commitments to her in favor of Heather. She angrily tells Hiccup that his brain is under siege.

In Heather Report, Part 2, Hiccup wanted to shadow Astrid on her mission to Outcast Island because he wants to be sure she'll be safe.

Later, when Alvin grabs Astrid and runs off with her Hiccup gives chase. Hiccup was also ready to kill Alvin when he threatened Astrid's life.

Before Heather leaves she gives Astrid a good-bye hug, and appears to not even notice that Hiccup was expecting one as well. It appears that Heather had picked up on Astrid's feelings and is keeping her distance out of respect for her new friend.

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 doing the right thing and 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.

When she and Stormfly fly him to the top of the ship's mast, she's genuinely worried about his safety during the electric storm.

Twinsanity
Astrid and Hiccup almost appear to think alike as they try to get Barf and Belch out of danger.

Breakneck Bog
When the other teens want to flee Trader Johann's ship and the Smothering Smokebreaths, Astrid is the only one to stay behind to help Hiccup find the treasure said to be from his late mother. She manages to talk the others into staying and helping, too.

Gem of a Different Color
Gobber pairs Hiccup and Astrid together for hand to hand combat, but Hiccup quickly protests, insistent it's not a fair match. It's unclear if he does this in an attempt to be a gentleman, or if he knows Astrid would win with no contest. He manages to dodge her first swing, but is quickly pinned to the ground. At Gobber's advisement, he then plays dead, and she gets off of him. As she's helping him back to his feet, she asks if he's ok, and he jokes that his shoulder should pop back into place in no time.

We Are Family, Part 1 & Part 2
When Hiccup is upset that they didn't find any other Night Furies for Toothless, Astrid cheers him up saying that Toothless is pretty happy anyway, because Hiccup is his family.

Live and Let Fly
Astrid and Hiccup are comfortable walking closely side by side on their way back from the arena. When Astrid catches Hiccup flying Toothless against his father's wishes, she chases him down on Stormfly, despite that meaning she was also breaking Stoick's new rule. When she catches him, Hiccup confides in Astrid his feelings on the rule, and they come up with the Secret Dragon Flight Club together. They then explain it rest of the other teens together.

The Night and the Fury
Hiccup gives Astrid the authority to arrange an exercise for the riders, and fully supports what she decides to do.

Tunnel Vision
When Astrid tells Snotlout that she's sure that's not what Hiccup meant when he started selling water in trade for goods, he says, "Well, that's what makes him Hiccup and me Snotlout." She responds, "That's just the tip of the iceberg."

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 knows that he thinks about her.

They spend a lot of time alone together on Toothless, chasing the Flightmare. When Astrid gets sprayed by the Flightmare's mist and is paralyzed, Hiccup pushes her to the ground to dodge another attack, and then drags her by the waist to the safety of Toothless, where he lifts her into the saddle. Her fascination with the Flightmare impairs some of her judgement and he has to push or pull her to safety a number of times. At the end of the episode when they were back in the village Hiccup said to the villagers "We learned alot about the filghtmare and I will explain it all to you but the most important thing we learned was Fearless Finn Hofferson was indeed fearless," Then towards Astrid "just like all the Hoffersons." Then he put his hand on Astrid's shoulder and they smiled at each other.

Appetite for Destruction
When Hiccup prepares to leave Dragon Island to find out what's making the islands to sink, Astrid insists to go with him, saying that it could be something dangerous, showing that she cares for his safety. Later, when Hiccup goes to confront the Screaming Death, Astrid again insists to go with him and when Hiccup tells her to stay for her safety she ask him "So you're leaving me alone?" even though Fishlegs was here too and even reminds her of that.

Ironically this is also the episode where Astrid tells Fishlegs "No one is kissing me on the lips, EVER!"

A View to a Skrill, Part 1 & Part 2
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.

The Flight Stuff
They're sitting awfully close together on the arena wall watching Snotlout train Gustav, their hands almost appear to be touching.

Free Scauldy
Astrid gives Snotlout a taste of his own medicine by flirting with him, and demonstrates the humor of it for Hiccup. Hiccup awkwardly admits that she's even grossing him out.

Frozen
She runs and hugs Hiccup in front of Gobber when he returned from rescuing Johann, relived that he's ok after half of their village was paralyzed by the Speed Stingers.

A Tale of Two Dragons
When Astrid knocks on Stoick's and Hiccup's door, Hiccup answers it saying "Ooh what a beautiful night, let's talk outside!" She vents her concerns to him about Snotlout, and he promises to deal with the issue. She then tells him "thank you" with a smile, and he flirtatiously leans toward her and says "you're welcome!"

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. He also calls her "young lady" and tells her to get inside.

Cast Out, Part 1 & Part 2
He saved her after Snotlout knocks her and Stormfly out of the sky. He has to hold Astrid back by the waist as she's trying to beat Snotlout up for what he did. Hiccup angrily suspends Snotlout from the academy for almost killing Astrid.

Race to the Edge
By the time of the episode Blindsided, Hiccup and Astrid are officially a couple. However, even before the events of Blindsided, it seems as if they both had feelings for each other, and were both aware of their mutual attraction towards one another. Also, 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 1 & Part 2
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 pushes 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 developed 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 asks her, "So, what are you in for?",to which she replies, "Not funny!", and when Hiccup is "locked up" she asks him the same thing. This indicates that they like to make fun of and tease one another.

Have Dragon Will Travel, Part 1 & Part 2
In "Have Dragon Will Travel, Part 2", 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 teases 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
Main article: The Next Big Sting

Astrid is visually concerned, biting at her fingers, when Hiccup jumps off the cliff with his new flight suit; Dragon-fly 1. She looks to Toothless for some reassurance that he'll be ok. Later, when Hiccup says the Stingers' webbed feet have given him some ideas for "something he's been working on", Astrid yells that if he says "Dragon-fly 2" she's going to lock him up, indicating she's sick and tired of him needlessly putting himself in danger.

Astrid's Team
After an attack on Berk, Astrid finds out that her parents house got destroyed during the attack. Fortunately, her parents were 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 but he was really trying to support her. When she decided to stay on Berk to train new riders Hiccup stayed too, he said it was to patrol the island but he really stayed on Berk to be with Astrid.

Night of the Hunters, Part 1 & Part 2
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 in 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 1 & 2
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.

Maces and Talons, Part 1 & 2
When Astrid is worried about Heather's safety while working with the Hunters, Hiccup reassures her that she would be fine, and they look longingly into each other's eyes until Snotlout and Tuffnut destroy the moment.

Enemy of My Enemy
At the beginning, she confronted him because he wanted to go on a patrol alone saying that is too dangerous and trying to convince him that he won't find Viggo. She was worried that he would wear himself into the ground looking for Viggo.

After she realizes that she can't change his mind, she said "Okay, if you're going, at least let me and Stormfly go with you." to which he replies "Fine!". However he left without her when she went to get Stormfly.

Later at the island when Toothless is incapacitated and Hunters are looking for him, Hiccup mentally beats himself up for not listening to Astrid.

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 off Stormfly, but he caught her and shushed her softly, telling her that they would beat the illness and that she must keep fighting, confessing that he couldn't imagine a world without her in it (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. He held her hand, and begged her to stay alive a little longer, for him.

When Viggo arrived to take the dragon, he revealed that it was his boat where Astrid caught the Scourge, which made Hiccup's hatred for Viggo double, especially when Viggo threatened to kill the dragon. Hiccup begged him to let them have the cure and Viggo could have the Buffalord, 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. When she tried to stand up by herself, she lost her balance and nearly fell to the ground, but Hiccup was there and caught her.

After the Viking funeral for the fishing boat where she got sick, Astrid thanks him for saving her life and she added that she owed him, after which he tells her that it wasn't a big deal and he was sure she would have done the same for him. She too confesses she couldn't imagine a world without him in it, as the both of them smile at each other.

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 safety.

To Heather or Not to Heather
When Astrid and Heather are talking, and Heather mentions Hiccup, Astrid smiles and looks to the ground. Heather tells her to to express her feelings and that the two of them are perfect.

Stryke Out
When Snotlout accidentally gets Hiccup and Toothless captured and taken to the 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, though Fishlegs said that Astrid would've killed him if they hadn't found Hiccup.

Tone Death
When Snotlout states that Hiccup can "have" Astrid. Hiccup laughs and says, "Thanks, I appreciate that".

Last Auction Heroes
When the riders were captured, Astrid puts 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.

Midnight Scrum
When they are alone in the Great Hall she places her hand on his and tells him to inform Stoick about the bounty. After Astrid and the other riders find Hiccup she immediately rushes over to him and helps him stand without his metal leg.

Dire Straits
After dragging Hiccup on deck Astrid calls his name, feeling worried that he isn't breathing. When he finally wakes up she is relieved to see that he's okay and puts her hand on his shoulder. It shows how much she cares for Hiccup and wants him to be safe.

Out of the Frying Pan
Astrid starts to panic when too much time has passed after Hiccup, Fishlegs, and Mala enter the cavern. She agrees to join Throk in fetching them before the lava rises too high, putting themselves in danger. Just before she passes out Grimm the heat in the lava pit she mutters Hiccup's name and when Hiccup, Fishlegs and Mala spot Astrid and Throk, Hiccup lifts Astrid onto his lap to take her to safety.

Blindsided
After Astrid was blinded and knocked over by a strike of lightning, Hiccup expresses his concern over her condition, speaking with her alone and trying to reassure her that everything will be okay.

Later, while riding on Toothless, Hiccup grabs Astrid's waist to prevent her from falling off, telling her to hold on tighter. She apologizes, but he says that it's okay, admitting he's glad that she's there with him.

When they land, Astrid begins walking off to find Stormfly, when she trips over a rock and Hiccup leaps for her, wrapping an arm around her waist and shielding her head from hitting the ground as they fall, leaving them in an awkward situation. When the Triple Stryke first appears, Hiccup pulls her out of the way and shortly after has Toothless grab her and move her to a safer position. Later, Hiccup tells Astrid that Stormfly was only protecting her when she was cast of to the side by her dragon.

Hiccup cheers her up and tells Astrid that he is there for her, that he will always be there for her, that there will always be a Hiccup and Astrid, and that she is far from useless in her current state. Shortly after Hiccup says this, the Triple Styke returns and Hiccup dives for Astrid pulling her to the ground with him and out of harm.

At Astrid's hut, Gothi finally helps Astrid regain her sight, with Hiccup saying thank you to Gothi. Astrid suddenly sees Hiccup and hugs him, with him reciprocating in kind.

After Astrid gets cured, she and Hiccup are sitting by the Dragon stables, when all of a sudden Hiccup moves as close as possible to Astrid. Astrid then asks Hiccup why he did not kiss her when the opportunity arose. Hiccup states that he was waiting for the perfect moment to do so. Astrid replies that right now is the perfect moment, and then Astrid and Hiccup share a kiss, and with it their romantic relationship is started.

Shell Shocked, Part 1
Astrid congratulates Hiccup for creating the perfect plan to capture and defeat Viggo, but while Hiccup is still nervous and unsure, Astrid assures him. They attempt to share a kiss until they are interrupted by Fishlegs, but he instead believes they're thinking of ways to hide the Dragon Eye once regaining it, completely oblivious of their romance.

Hiccup and Astrid are relieved and decide for the time being to keep their newly formed romantic relationship a secret from the rest of the Dragon Riders.

Eventually, the rest of the Dragon Riders being to notice a change in Astrid and Hiccup, but all are oblivious of their newly developed romantic relationship and instead theorize different reasons for their behavior.

While Ruffnut and Tuffnut believe that Hiccup is going to die and Snotlout believes he has developed a gambling problem, only Heather becomes aware of their romance and allows the couple to have time alone together.

Shell Shocked, Part 2
Viggo knows of Hiccup and Astrid's relationship, and taunts him with it, telling him how odd it is that he is in love with a girl who is also with him in battle, which winds Hiccup up, forcing him to concentrate on the task at hand, stopping Ryker.

After defeating Ryker Hiccup goes to check on Fishlegs, after Fishlegs leaves Viggo appears while holding Astrid captive and states that he will release her in return for the dragon eye, causing Hiccup to throw it into the volcano which makes Viggo let go of Astrid and run to it, this show how Hiccup will do whatever it takes to protect Astrid. At the end of the episode, just prior to the explosion of the volcano on the Edge, Hiccup and Astrid were kissing after promising to keep their relationship out of the war with Viggo, but they were seen by the Riders, erasing Ruff and Tuff's suspicions about an 'illness'. Snotlout, on the other hand, seems to be convinced of a gambling problem.

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.

Burning Midnight
After being trapped in a cave surrounded by rogue dragons, the gang share stories and Astrid retells the brief events of her conversation with Stoick before heading off to Itchy Armpit. Valka, upon hearing the story, expresses her gratitude to Astrid for taking care of Hiccup and being the daughter she and Stoick always wanted.

The Serpent's Heir
Before heading off to Nepenthe, Hiccup decided to make Astrid the acting-Chief. Astrid, however, ends up appointing Gobber as her acting-Chief so she can join Hiccup on his visit to keep him out of trouble.

After returning back to Berk, Hiccup appoints Astrid to the General of Berk so they can lead Berk as a pair by working together as Chief and General.

Deleted Scenes
How to Train Your Dragon: An Axe to Grind

An Axe to Grind was deleted because of the length, not the content. It's therefore considered canon.

This deleted scene gives insight into Hiccup and Astrid's relationship prior to dragon training. It also shows Gobber encouraging and teasing Hiccup about his crush on Astrid.

Near the end of the scene, Astrid thanks Hiccup for sharpening her axe and then brushes her bangs away from her face with a smile. She does the exact same thing before kissing him in the cove and after almost kissing him in "Animal House". This suggests that there might have been some aspects about Hiccup that already appealed to Astrid.

Gift of the Night Fury: Missing Toe

Everyone else has black eyes suggesting Astrid had punched them in the face, while Hiccup still gets his signature punch in the arm.

Trivia

 * Hiccup and Astrid relationship is usually shortened to "Hiccstrid" when referred to in a romantic context. It is mentioned on-screen for the first time in Race to the Edge: Season 4 episode Shell Shocked, Part 1 by Snotlout.
 * 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 7 times.
 * They are the only ones throughout the franchise who kiss besides Stoick and Valka.
 * As of How to Train Your Dragon 2 Hiccup and Astrid are the only Riders who are dating.
 * 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 HTTYD2 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.
 * Their relationship officially starts to take form in Race to the Edge: Season 4 in the episode "Blindsided", and it was intended to stay secret, however, they were seen kissing by the gang at the end of "Shell Shocked, Part 2."
 * According to an upcoming interview with Richard Hamilton; "Hiccup and Astrid lead Berk as a pair by working together as chief and general."

Quotes
The page for quotes about Astrid and Hiccup's Relationship is here