It’s obvious that Dagur has a love for tormenting Hiccup and anybody else that’s easy to prey on, or that’s what Hiccup’s and Fishlegs’ dialogue in RoB’s episode fifteen ‘Twinsanity’ seems to tell us.

Hiccup: “Cool?! Last time he was here, he used me as a knife throwing target.”

Astrid: “That guy should be locked up in a cage!”

Fishlegs: “That’s what he did to me! He wouldn’t let me eat for three days!”

Snotlout: “*laughing* then he force-fed you rotten cod heads!”

Fishlegs: “Thanks. I almost erased that from my memory.”

So it’s obvious from the start that Dagur just likes tormenting everybody he finds an easy target, notice how Astrid most likely had no idea, judging by her angry comment.

What’s interesting is that this thing, this obsession didn’t start until after Hiccup saved his life and we see him again in DoB’s third episode ‘The Night and The Fury’.

Dagur: “Hiccup, old friend! You’re alive!”

Hiccup: “Uh, last time I checked. So… Haven’t seen you since-”

Dagur: “Since you saved me from that dragon attack back on Berk. You fought off a Night Fury!”

I especially love his face here, look at how touched he is that Hiccup saved his life.

Dagur: “And you were like - WHAM, WHAM- *swings sword* “Dagur! Save yourself!” And I was like “what?! Okay, I’m outta here!” But you stayed!”

Dagur very clearly has a sort of fondness, maybe even an infatuation, with Hiccup at this point, stemming from Hiccup rescuing him heroicly from a Night Fury.

Something that might back this up is the ‘Twinsanity’ episode.

Dagur: “Ah, Hiccup! There you are!”

Hiccup: “Dagur! Was just thinking about you! Hey, remember that time we went swimming and you tried to drown me?”

Dagur: “*laughs, a lot* Oh, the laughs we had. Bored again! *pushes Hiccup aside*”

Dagur: “Just a moment. Something is going on here.”

Hiccup: “I can explain.”

Dagur: “Where is it?”

Hiccup: “Look, it’s just one drag-”

Dagur: “Your leg.”

Hiccup: “…”

Dagur: “Nevermind, I heard all about it.”

Hiccup: “You heard all about what?”

Dagur: “You. The Red Death. Defeated it all on your own.”

Hiccup: “Wha?! Me?! Look at me! How is that even possible?”

Dagur: “Right? That’s what I thought too! But then I heard about the trained dragons and it got me kind of… tingly.”

This could, of course, just be Dagur feeling “tingly” about the possible dragons on Berk, but what could also have Dagur feeling “tingly” is that Hiccup really did fight and defeat the Red Death. He is missing a whole foot and part of a leg, after all.

And like, he gets all up in Hiccup’s personal space when Hiccup explains that the Night Fury got away and Dagur suggests hunting it down together.

Clearly, Hiccup is having none of that. Look at how scared the poor boy is. That isn’t just discomfort, that’s straight up worry and fear.

Then there is this piece of dialogue as he does this.

Dagur: “Come on! Howl with me! It feels good.”

And let’s not forget these golden lines.

Dagur: “Hiccup, every since I left Berk, I haven’t been able to stop… thinking about you.”

Hiccup’s reaction is a very appropriate “O_O” as Dagur, of all people, almost seems to be confessing to him. And it looks genuine too judging by his expressions. I’ll be getting back to this again soon.

And Hiccup seemingly knowing the Night Fury he fought is the very reason Dagur is on Dragon Island in the first place! Hiccup inspired him.

Hiccup: “Well, that’s kind of strange… Well, I’m flattered!”

Dagur: “Not you personally, you and that… Night Fury! It’s like you knew that dragon! You were inside its head, rattling its cage! And that, my muscularly challenged friend, that’s when I knew I needed to know about dragons too! So I came here and I learned about them. One. By. One.”

So Hiccup definitely served as an inspiration for Dagur to come to Dragon Island. And let’s not forget, Dagur doesn’t even know at this point whether Hiccup survived his “attack” on the Night Fury or not.

It does seem like Dagur was using this dragon hunt on Dragon Island to bond with Hiccup. Confessing about being inspired by him, talking dragons, talking personal weapons of choice, even telling him about his sister, who was already missing for a long time now at this point and probably even a heavy subject to just casually mention like that.

Hiccup: “Whoa! Nice crossbow…”

Dagur: “My hunting weapon of choice. You carry… Hmm, just a shield?”

Hiccup: “Yeah, yeah, just-just a shield. Just a plain old shield.”

Dagur: “Very… ornate. My sister had one like that. I myself have never felt the need to hide in combat.”

Besides bonding with Hiccup, it’s also like Dagur seems to be testing him too.

Assuming that Hiccup is there to hunt dragons, questioning him about the Night Fury’s fate, sounding dissatisfied when he tells Hiccup about never having the need to hide in battle.

Definitely feel like Hiccup is being tested by Dagur during this episode. Nevermind how he treats him.

Look at Hiccup in that second pic. Dagur’s grip on him was clearly hard enough, painful enough, to get him to sooth or feel that spot once he finally let go.

Dagur: “I know it’s on this island, Hiccup. I can feel it right here.”

Look at that face down below, just before Dagur decides to invade Hiccup’s privacy again.

Dagur: “You can feel it too. Don’t you, Hiccup?”

This counts as unwanted touching.

Also this:

Hiccup: “Ah no, I just feel really awkward.”

Dagur: “*laughing maniacally and pushes Hiccup to the ground, hard* You bring the funny, Hiccup! I’ll give you that!”

And!

Dagur: “I’m gonna grab my gear. Then, we’re gonna get us that Night Fury… Brother.”

Hiccup: “… Brother?”

Dagur: “That’s right, you and me.”

So yeah, we can tell from this one scene alone that Hiccup’s “Don’t worry, Dagur won’t hurt me. I’m his brother.” has always been very ominous and Hiccup basically put himself in a very precarious situation by separating from Astrid, Snotlout and Fishlegs.

I get it, they had to find their dragons and stop Dagur from hunting down and harming Toothless, but that is still quite a risk Hiccup took, considering Dagur’s current behaviour and their shared history.

Like, look at Dagur’s face when Snotlout pops up and he realizes Hiccup isn’t alone.

Clearly an “explain yourself” type of expression. But whether it’s a “my newest bestest friend is a liar” or a “my new crush lied to me and isn’t alone” type of expression, I don’t know. And that while it turns out that Dagur didn’t exactly come alone either later in the episode.

Like, Dagur gets obviously pissy when he discovers Hiccup’s friends are on the island with him while knowing that he had a whole armada there with him.

AND LET’S NOT FORGET DAGUR JUST CASUALLY BRINGING UP THAT HE WOULD GLADLY OFF STOICK SO HICCUP CAN BE CHIEF.

Dagur: “You know, we’re a lot alike, Hiccup.”

Hiccup: “Really? How-how-how is that?”

Dagur: “Well, we’re both born leaders.”

Fishlegs: “Oh yeah, he’s right about that.”

Dagur: “Sons of chiefs.”

Hiccup: “Yeah, that’s true.”

Dagur: “Who had to be eliminated so we could gain control.”

Hiccup: “Yes,- Wait, what?! No. No! My dad hasn’t been eliminated from anything!”

Dagur: “But he could! Easily! Just say the word and I’ll- *fires his crossbow, aiming between Fishlegs and Snotlout*”

Hiccup: “…. Yeah, that’s… something to think about.”

So Dagur has definitely offered Hiccup to kill his father for him so they could both realize their respective birthrights to be chief. And at this point Fishlegs and Snotlout, while previously disturbed by Dagur’s want to hunt dragons, are now downright fearful themselves.

To the point that Hiccup feels the need to try and reassure them that Dagur won’t hurt him because he’s his “brother.”

Then there is also Dagur’s line. “Oh Hiccup, don’t you know that a trapper’s trap can trap the trapper?”

How big of an impact didn’t this one night have that Hiccup not only repeats this line three years later, but that he somehow manages to say the exact same thing word for word.

I wouldn’t be surprised if this night had an impact on Hiccup, Astrid, Fishlegs and Snotlout.

But that one scene that I was discussing in great detail pretty much only sets up Dagur’s infatuation with Hiccup, which apparently also includes a series of tests so Hiccup would need to keep proving himself as the object of Dagur’s fascination, whether he wants to be or not.

It’s that final scene from this episode that actually turns Dagur’s unhealthy crush into a full-blown obsession. When it turns out Hiccup didn’t actually save Dagur’s life and has been lying to him ever since that day on Berk.

Dagur: “Your father lied to me- YOU lied to me!”

Hiccup: “He was trying to keep the peace between our tribes. So was I.”

Dagur: “By making a fool?! Out of me?!”

Hiccup: You don’t really need a lot of help with that, Dagur”

Dagur: *attempts to draw his sword*

Toothless: *snarls*

Hiccup: “Your move.”

And not only does it turn out that Hiccup has been lying this entire time, but then he proceeds to call Dagur a fool and, in a way, threatens him with Toothless.

Look at these faces. When he states that Hiccup “could’ve been his brother” and is now his enemy instead and Hiccup not only just accepts it, but also threatens him again? Look at that heartbreak! Look at that anger! This is just before Hicctooth tries to fly away and Dagur immediately flings a bola at them and then proceeds to try and kill Toothless, even with Hiccup in the way.

In a way, Dagur had hoped for this night to turn into something.

And it did, just not in a way Dagur would’ve wanted.

And it’s basically because of this night not turning out the way Dagur would’ve wanted it to that he decided to go to war with Berk. He just focussed on hurting Toothless because hurting Toothless meant hurting Hiccup. Just like at the end of DoB, when Dagur took Stoick away and tried forcing Hiccup to choose between two of the most important people in his life.

So yeah, sorry to go so ham on your ask again, but these are the reasons why Hiccup’s line is as ominous as it is.

There are several red flags all over the place that aren’t just making him uncomfortable, but his friends as well.

And it basically only grows worse from here.

^^^^^ Hiccup doing a double take to make sure they’re not being followed.

Comfort

Toothless wasn’t sure what he was looking for in the Haddock Household. He ransacked the living room, pretty much stuck his nose in every possible nook and cranny and pot in the kitchen and now found himself sniffing through Hiccup’s stuff in their bedroom. After all that searching, he still hadn’t a clue as to what he was actually hoping to find.

He wanted something comforting for Hiccup, that was certain. Something his Rider could be soothed by during these trying times.

A pillow? No, he had one already.

Blankets? And risk having him overheat? Never!

His little notebook and charcoal pencils? How on Midgard was the boy supposed to write or draw in his condition?

Just then, as a chair overturned by a careless push of his shoulder and ended up on the wooden floor on its back, Toothless’ gaze caught the sight of just the thing he was looking for and it was silently gazing back at him with tiny black eyes.

The little dragon toy. The same one Hiccup had gotten back last year and of which the presence often gave him great comfort after a nightmare or a hard day.

It had been made by his mother when he was just a babe and the boy had once mentioned that it made him feel like she was still with him, although he couldn’t remember her no matter how he tried.

So it was the toy that Toothless took. Careful to take it with just his gums and trying in vain not to get it covered in slobber, he returned to the Great Hall, where his Viking rested.

The second he entered, an utmost foul stench hit his nose. He wondered if it was a pungent for the humans as it was for him.

It was the stink of disease and death as Berk had been hit by another Eel Pox epidemic. It came annually and it was easier to get the ingredients for a cure now that the Hooligans had dragons, but it was particularly bad this year.

Hiccup was one of those that had fallen ill.

Stoick claimed that his son rarely caught anything, but then someone else responded that this only meant that, should Hiccup get sick, he would get really sick. And that is what worried Toothless so.

He navigated through the people stumbling about, frantically caring for their sick, evaded the cots on the stone floor of the hall and quite quickly found the boy he was hoping to find.

The Night Fury was disappointed to see, after arriving at his Rider’s side, that he was still asleep.

He had yet to wake up today.

Which really did nothing to ease the dragon’s concerns.

Hiccup was lying on a cot, curled up on his side with the covers drawn up to his cheeks. He looked even paler than usual and thinner too. He lost weight, of which he didn’t have much to lose in the first place. A fever kept him hostage.

His father sat by his side on a stool, off in slumberland himself as he had been up on his feet and caring for his village with little sleep for days. The man would’ve collapsed if he didn’t get some rest.

Sharpshot was present too. Curled up around Hiccup’s head and breathing out little puffs of smoke. It was as if he were protecting the boy, sleeping and watching over him to fend off something he could not physically fight.

Though now drenched in saliva, Toothless still put the dragon toy down in front of him, gingerly pushing it into his arms with his snout. It displaced the blanket he slept under, but he could fix that soon.

Hiccup seemed to grab for it in his sleep, unconsciously, the first sign of life they got all day besides his breathing.

He seemed to be curling up in an even tighter ball and Toothless managed to fix the covers after he moved. He liked being cocooned, the Night Fury noticed.

Toothless settled on the floor by his side and gave his temple just the tiniest lick, to which the Viking didn’t respond.

A worried croon left him and Toothless placed his head down.

He hoped Hiccup would get better soon. It was terrible to watch him grow sicker and sicker by the hour, but he preferred that greatly over the completely still figure he now was.