"Toothless no!" He shouted as his own dragon, his own friend lunged in for the kill. It was a blur of black and green and… sky. He wasn't falling, no, he was laying on his back, face towards the sky and watching the clouds roll. He blinked. What?

He rolled onto his forearms looking around for Toothless or for answers as to how he was alive. Those answers came in the form of Jack who Hiccup assumes had shoved him out of the way. That meant Toothless was somewhere in the water below. Hiccup quickly thanked the Gods that that dragon could swim.

He thanked the Gods that Jack was alive. If it hadn't been for some stroke of luck or impossibly fast reflexes, Toothless wouldn't be the only one who'd have to swim to shore.

He heard it before he saw it, and Gods did he wish he hadn't seen it: the ground breaking. His head snapped up to meet Jack's gaze. Except Jack was somewhere else, there was this… look that crossed his features.

Hiccup reached out as if he could stand and make it there in time to save him, yet all he did, all he could do, was watch Jack fall.

He jolted awake so fast that by the time he opened his eyes he was already upright, heaving and unable to breathe. It was as if he ran a couple thousand yards. He could hear his heart hammering in his ears like drums as the feeling of falling receded.

He hated these nights and the dreams that came with them because not only did it remind him of his stupid inability to save the people that he cares about, demolish his sleep schedule, and have him wake up absolutely petrified, but the nightmares always seemed to make him feel what Jack was feeling in the moment despite it being from his perspective. As if they were connected in some sort of way. He knew even as it was happening that Jack's expression would be burned into his mind for the better part of a lifetime at the least.

It wasn't the first time he'd seen death obviously, what with the dragons and everything? But it was the first death he'd been directly correlated to and the first death he'd probably remember for the rest of his life. He hadn't even known Jack all that long or well, but the thing about Jack is… he's unforgettable.

He felt Toothless nudge him, probably awoken by his thrashing, "hey bud," he said, but it was quiet and his voice came out hoarse. Toothless nudged him again and this time Hiccup, who did really need a distraction, sighed, knowing what the dragon wanted, and absentmindedly motioned for the reptile to go get his prosthetic, still lost in his own thoughts.

So far, the universe had been generous to him and the Riders, it'd been about a week and a half since what they had dubbed the 'Grimora Incident' and so far they've gotten by with minimal 'episodes' as Astrid would probably call it, minus the nightmares of course. But then again, who's to say that's a good thing and not some prophecy of doom.

Toothless dropped the prosthetic in his lap causing him to let out a noise of disgust at the sheer amount of dragon drool the cat-like lizard had somehow managed to coat the thing in. He put it on anyway.

Hiccup silently walked out of his hut, he was too tired for a flight and he was sure Toothless felt the same so instead he opted for just walking on the planks that connected their huts together. It was peaceful, the air was cold but for once not frigid, and the moon shone down from the sky which was cleared of any clouds. Hiccup realized that despite always being airborne he never took the chance to actually look at the sky.

Just like he'd never really taken the time to think about death. Maybe that was why he was so reckless, because he never really cared what happened if things went south. Would it hurt? For how long? He guessed it depended on the death. Is not that he was scared of death now, but the fear that had flashed in Jack's eyes spoke volumes about what the experience would entail and personally? Not something Hiccup wished to experience. Of course he's thought he was going to die in the past, but those times he was ready, he knew the risks and the chances and took them anyway. Jack's death was so sudden and Hiccup forgot that death could be like that sometimes, it could sneak up on you without warning. But was that better or worse?

Well that was… depressing, he almost rolled his eyes at himself after realizing what it would sound like if he ever dared to speak those thoughts aloud to anyone. I'd be shipped off to sea, definitely.

Toothless growled from beside him. "What is it bud?" He asked, turning to his friend and watching him snarl at Hiccup's own hut. For a moment Hiccup, being the person that he is, thought Toothless saw the look on his face and opted to actually tie him up on a boat and send him out to sea. Then he remembered that Toothless wouldn't even be able to physically manage that.

"You smell something?" He whispered as he carefully crept towards the doors of his home Toothless standing guard right behind him. Yet the closer Hiccup got to the doors the more confused he became. There was no noise, no visual cue, no sign of life at all that could've got Toothless to become so aggressive like that.

He flung the door open, with Toothless immediately ready to fire. But there was no one. Absolutely no one, everything was the same as when he left it, the entire place looked painfully untouched. "Come on bud, you can't scare me like tha–

He was interrupted by Toothless completely ignoring him and instead bounding off towards his desk as if he was excited, causing Hiccup to stumble slightly. "What was that about?" he asked, walking over to where Toothless was now wagging his tail, something he usually only did when he was either very excited, or extremely happy, two levels of emotional status he usually only achieved when Hiccup finished a new invention or right before a morning flight. This made Hiccup feel very confused.

"What'd you find there bud?" He asked, lightly rubbing his hand on Toothless's snout before turning back to the desk. What he found made him even more confused. Clearly there had to have been someone here at some point because there was a very ominous letter rolled up and innocently sitting on his desk waiting to be opened.

Not only that, he couldn't figure out what exactly about this letter had Toothless so riled up. He looked back to the dragon in question to find him looking from the letter to Hiccup, big round pupils bearing into Hiccup's soul and begging him to open it. He sighed, "only one way to find out," he said, shrugging slightly and then opening the letter. Hiccup stared at the words that sprayed across the parchment, read it, then read it again. He blinked multiple times, this couldn't be real, and yet here it was, in his hands.

°•○●○●○●○●○●○● ◇ ●○●○●○●○●○●○•°

He could feel the irony like the gravity that was pulling him towards death at this very moment. It pulled him down like hands inviting him to lay in the water with his memories, just one more time.

For a moment there was pure terror. Just absolute, joint locking, stomach dropping, terror. Jack's mind raced through a thousand different regrets but out of all of them his biggest regret is having the audacity to think: This is probably going to scare the shit out of Toothless, promptly followed by the urge to laugh and: I'm going to Hell.

He might actually too, which was the funny part. At least it was funny to him. Then, as the wind ripped tears from his eyes and the water grazed his back he was yanked away. He almost blacked out from the sudden headache it caused, it felt like being thrown onto a dumpster. Why do I know what that feels like? The wind around him drowned out the sound of pain he let out. He assumed Artemis had saved him but he couldn't be sure it wasn't one of the Dragon Riders until his spotty vision cleared up. He tried to clear his head faster by shaking it but all that did was make it hurt more.

He quickly shut his eyes and just decided to wait it out for the moment. Now I know how Hiccup felt. Jack remembered when he caught him and instantly felt sorry for the poor guy. Don't get him wrong he's fallen off Artemis more times than he could count but Artemis never caught him this harshly. Nor had he ever been this deprived of food and water. Now that he thought about it, the last time he even drank water was two days ago. …Oops?

Just like that Jack momentarily forgot the extent of his situation. Bringing himself back to the present reality, Jack looked up to find that he was neither saved by Artemis or the Riders. No, he was saved by a… flying boulder? A Catastrophic Quaken if he remembered correctly. They were very moody and usually very territorial and they usually didn't leave said territory to save reckless, irresponsible teenagers that almost get themselves killed.

Then he was yanked again, this time out of the way of plasma blasts. Pink and yellow explosions seemed to materialize in the air, heating it and piercing Jack's ears. "Arti!" He shouted watching as her eyes narrowed in concentration before straining to place his feet on the Quaken's stomach so he could quickly kick off. The action seemed to almost rip his arms out of their sockets but there wasn't really time to think about that at the moment. He was falling again and the terror was back, only this time there was a familiar element of thrill, in other words, there was terror but no panic, not when Artemis was there to catch him.

He grabbed onto his dragon like a lifeline and just like that he was flying again. "What took so long?" He asked, slightly annoyed, then lifted his hand, "wait- are you… wet?" He asked now in pure confusion as he examined the water that had collected on his hand. Artemis grumbled and (probably) rolled her eyes.

He looked back to find that Grimora island was now a faded mass of rock in the distance. As for the Quaken, Jack found them hovering not too far away from him and Atremis. Then Jack noticed there was someone riding the Quaken, he tensed knowing that the odds of finding more and more dragon trainers in the span of just a year was slim. The only thing keeping him from blasting this guy off his dragon was the fact that that possibility was 'slim' not impossible. There was also absolutely nothing keeping this stranger from seeing his face. "Who are you?" Was the only thing he could think to ask. The person in question didn't respond which was weird considering that mostly everyone in the Archipelago would boast about their name till the ends of the Earth. Valka being the exception of course.

When the stranger flew forwards Jack pulled back. If he squinted he could make out a head of short blond hair, if you could call that bond, a more accurate description would be straight up yellow. That was the only feature Jack could make out however and even then, for all he knew their hair could be brown with the Sun shining into his eyes.

It'd been about a minute and the rider still hadn't done a thing, not even speak. Which was the problem because Jack was known for anything but his patience and he figured that had they actually wanted to harm him they would've done so by now and same goes for if they wanted to be friendly.

Yet when he steered Artemis away hoping to escape both Astrid's wrath the Riders plus this new variable in the mess that was his overly complicated life, (Existence?), and report back to Valka about said variable, the stranger chased after him even while being no match for they're speed. Now, Jack would've just cloaked invisible, that is, if it weren't for the fact that Artemis wasn't quite fully dry. The water that clung to her scales despite the cold rush of air hindered their ability to cloak themselves similar to how it hindered a Zippleback's sparks.

"You know, when I find out the reason you're soaking wet, you will never live it down," he said, earning him a twist into the ocean. Jack thought it really said something about the things he let this damn dragon get away with when she could dunk him underwater Thalassaphobia and all with no consequences, "okay now that was just petty," he complained when she let him up.

Jack checked behind them to find that the Quaken and their rider had stopped and Jack hoped, he really did, that they had given up but of course, it's never that easy. Turns out Artemis decided to follow example and stop as well, "woah, hey– what's wrong?" He asked, receiving no indication that she'd even heard him. Meanwhile, the Quaken flew closer. "Hey Arti, now would be a really good time to let me know what your plan is here," he suggested, of course Artemis did absolutely nothing even as the Quaken came up almost right in front of them. "Okay then girl, if this is what you prefer… for… some… reason…" he told her, flattening himself a little more against her back warily.

°•○●○●○●○●○●○● ◇ ●○●○●○●○●○●○•°

Present day…

"Nice to see those three training on their own," he said to Astrid as they walked along the field next to the training dome. "Not really like them, though, is it?" She asked incredulously, yeah… on second thought, probably not training, he noted to himself, sharing a look with Astrid before taking off to follow the others, which happened to be Fishlegs's hut.

When they got there, the three teens were sadly and predictably, strangling and punching Fishlegs who at this point wasn't even trying to put up a fight, just wincing in pain. It was hard to watch actually.

"Whoa, whoa, whoa! Hey! What is going on with you three? And why are you all on top of Fishlegs?" He asked, watching as Snotlout tried to bite Fishlegs's arm, which wasn't even the sad part, the sad part was he was trying to do it through the leather arm guard when Fishlegs was wearing a sleeveless top.

"It's okay. Really," Fishlegs said, pitifully before Tuffnut held up what looked to be a letter, "Ha! The Fishmeister has been getting quite the bevy of Terror mails lately," he announced in victory. That's when they finally decided to all leave Fishlegs to suffer on the dirty wooden floor in peace, "and since we haven't been sending them…"

"That begs the question, who is our sly little friend here, communicating with on the…" Tuffnut filled in before pausing to think of a word, "...sly," he finished, waving the letter in a circle like a wand, "and because he won't give up a name–

"We decided to take matters into our own hands," Ruffnut finished for Snotlout.

"Okay, fine. If you must know–

"Oh, we must! We must!" Tuffnut declared.

"Yes, yes. We must!"

"Guys!" He interrupted, because he'd be hypocritical if he let this happen, but surprisingly, or unsurprisingly, that was the literal only reason, "Fishlegs doesn't have to tell you unless he wants to. It's his personal, private business," he told them, because it was and he wouldn't want them to do the same to him. "Well said, Hiccup," Fishlegs complimented, giving the others a triumphant look only to receive glares in return.

Eventually he sighed seeing Hiccup wasn't going to help him twice, "I've been corresponding with a certain someone who has been returning my Terror mails in kind, you happy?" He admitted, which shocked Hiccup less than the others might realize. "Are you saying what I think you're saying?" Astrid asked, clearly assuming something Hiccup missed in trying to figure out who in all the realms Fishlegs could be talking to.

"Fishy's got a girlfriend. Fishy's got a girlfriend," Snotlout sang, dancing around with Tuffnut, "who is she, Fishlegs?" Astrid continued after the duo of local idiots congratulated each other as if they'd accomplished something. In their minds they kind of had.

"Who said it's a she?" Snotlout asked, hanging off of Tuffnut, which for some unfathomable reason made Hiccup feel slightly weird, yet he ignored the odd feeling in favor of admitting that he was also shamefully curious. "Okay, okay," Fishlegs soothed, before dropping a bomb that was… shocking to say the least.

"It's Heather."

He heard Astrid gasp behind him while the others gaped openly, not saying that he wasn't either, but then again, why were* they so shocked? Honestly Heather was the most probable person in this situation, maybe besides Johann, "so, wait, you're telling me that my future wife, the future Mrs. Lout, who just disappeared after the whole Viggo fiasco, you knew where to find her and you told exactly no one?" Snotlout complained, as Fishlegs just stood there deadpanned, "Yep, pretty much."

"Look, guys, Heather is out on her own. She never stays in one place. We knew we'd hear from her eventually," and he knew he was stealing words from a separate source but bite him, they were good words.

"Yeah, but she and I have that connection. She should have written to me," Snotlout complained.

"Fishlegs, how many of these correspondences are we talking about?" Astrid prompted, to which Fishlegs turned and opened a chest that was sitting behind him. Hiccup was sort of impressed, the chest itself was overflowing with so many Terror mails that a few fell out onto the floor.

°•○●○●○●○●○●○● ◇ ●○●○●○●○●○●○•°

"Uh, wow. Those are some depressing Terror mails. I may need a mace to the head just to cheer me up."

"On it!"

A mace flew towards Ruffnut's head as prompted only for her to catch it without even looking up from the parchment, "Metaphorically speaking!"

"These letters don't sound like her. She seems worried and confused," Astrid stressed, looking genuinely concerned. "Think about everything she's been through. The only family she ever knew, gone. Then being out there, alone, by herself," Fishlegs said, and that struck something in Hiccup. Realization and worry flooded his mind, "and lest we not forget, or forget finding out her brother is one Dagur the Deranged," Tuffnut reminded them, "yeah. I can't say I'd feel any different in her shoes," he thought out loud, looking to the ground as if it could help him figure out what to do.

"Shoe."

Hiccup glanced over to Snotlout refraining from rolling his eyes, "because you... never mind."

"Hey, Heather's risked her life to fight with us," Fishlegs started in a passionate voice that effectively caught everyone's attention, "she's helped us save countless dragons. She's the closest thing to actually being one of us. It just seems like we should do something to help," he finished, which soaked an idea in Hiccup's head, "well, hey, what about making her one of us? Ask her to be a Dragon Rider," he suggested to which Fishlegs immediately expressed his approval. Tuffnut on the other hand…

"Well, I think it's a terrible idea. An awful, dreadful, unfathomable idea," he announced, but it came off as theatrical rather than serious and failed to carry any actual conviction, a detail that prompted Astrid to remind him that they were trying to have a serious conversation.

"So am I," he protested, "look, you don't just get to be a Dragon Rider. I'm surprised you didn't know that. We've spent the last five years fighting the nastiest, smelliest, most disgusting and often insane dragons out there. How many times have we almost gotten killed doing it?" To which Hiccup had to admit, Tuff had a point.

"There was the Screaming Death, the Whispering Death, the Red Death, all the other Deaths. And then there was–

"We get it, Ruff."

"So why does she get to waltz in here, all of a sudden, like she's one of us? Doesn't seem fair to me," he finished, crossing his arms as if he was proud of himself, "and besides, who said she'd even want to be a Dragon Rider? You know, it's not for everyone. I, myself, have had moments of doubt," Ruffnut added, and that was the final nail in the coffin for Hiccup.

"You know… Tuff's right, about all of it," he agreed, and Tuffnut let out a very confused and astounded, "What?"

"Well, let's invite her to the Edge. Just for a couple of days. To hang out, see how she's doing. Maybe she helps us redirect those Nadders. But nothing permanent happens without us all agreeing. Sound good?" He asked, and received multiple nods in agreement. Sensing that the discussion was over, the Riders all went off to do whatever they had scheduled for today. Hiccup himself had something he needed to check on, though he's checked so many times in the last few days he's started to feel like an impatient child.

Toothless perked up as well, gaining a slight shine of excitement.

Hiccup had kept in touch with Jack after the whole 'surprise I'm alive!' thing. He didn't think the others ever messaged him, instead they tried their best to move on, either that or they didn't have the time. When he revealed the letter to Astrid, she'd been predictably suspicious. Jack had informed them that a friend had saved him which left so many more questions than answers it was painful. Afterwards they never really brought it up again, it just felt too odd to talk about. In fact it felt so awkward that most of the time they didn't actually know how to bring it up.

Sure Astrid, the Riders and him had all come up with theories, some more ridiculous than others. But Jack fell off of a cliff into the ocean and never resurfaced. People can't just do that and survive. Of course Hiccup never saw him go under, he was too busy almost falling off himself to see what actually happened. And all that wasn't even considering Hiccup's own suspicions.

Sadly the letter wasn't there today either, Hiccup figured Jack was just giving Sharpshot a rest before having to send him off again. Said dragon always had to fly in through the back of the island in order to not be bothered by the rest of the Riders, if earlier today was any indication as to how they would react Hiccup might as well die on the spot. This meant that Sharpshot was always exhausted afterwards.

"Come on bud," he said, because he had a few projects to work on anyway. Most of the time, the letters were just random little thoughts and opinions they had floating around. Or maybe it was a response to one of Hiccup's many rants.

So far, they'd exchanged so many Terror mails he'd started having to burn the private ones and keep the ones that made him smile or laugh, and sometimes burn some of those too because there was no way he could keep that amount, it was embarrassing actually. At one point it got so bad he had to give Sharpshot a rest for a week before he'd even fly willingly again. Now he waits at least two days before sending the next one, or he just uses one from the flock they have available but that runs the risk of getting noticed and frankly Hiccup would rather not die, thank you.

When Hiccup got the first letter, he cried. As silently as possible of course, he didn't want to wake anyone up. Thing is, he could barely contain himself, Jack was alive.

°•○●○●○●○●○●○● ◇ ●○●○●○●○●○●○•°

Heather didn't know how she felt about being at Dragon's Edge, for one, the second she landed, she was immediately greeted by Hiccup and Fishlegs, on the other, the familiar and constant voice in the back of her head was telling her to run, fly away so no one got hurt.

Tuffnut said something about a Dragon's Edge welcome song but honestly Heather was more focused and excited about– "Astrid!" She cheered, running up to her best friend and hugging her. It felt nice, and was probably one of, if not the most welcoming thing to happen so far. Astrid always knew how to make her feel accepted, which was ironic considering how their relationship started, "I'd love to hear your song later, Tuff," she said, before taking Astrid up on her offer to get settled.

"Good. Oh, Heather, you're gonna love it. And now I have time to warm up."

"Good idea," she told him, walking off with an arm around her best friend's shoulders.

"You know, you could've come back with us in the first place. You just disappeared. We didn't know what happened to you."

Heather tensed, it was a conversation she was dreading, but, Astrid sounded more genuinely concerned than angry, "and I feel terrible about that," she started, just in case Astrid was angry, she could hide her feelings frighteningly well, "but I knew that you guys would just try to get me to stay. Sometimes you need to be by yourself to figure things out," she explained, turning around to face her friend. Astrid's blue eyes darted to Heather's tense shoulders and then back up again, "your letters to Fishlegs seemed like you were struggling with a lot," she pointed out, but Heather got the message, 'I get it,' and she relaxed a bit before realizing, "You read those?"

"We were all worried about you. We wanted to know what was going on," she assured, and her voice made Heather actually want* to talk about it, to finally get it off her chest to someone she cared about and trusted after carrying it alone for so long, "it was weird. All that time with Dagur, we were playing a part. I didn't have a minute to think about the fact that he is actually my brother," she explained, avoiding her friend's eyes, instead she looked to the floor, gripping her axe as if to block a blow.

"Maybe you shouldn't think about it then," Astrid suggested, and Heather realized she didn't need to block anything, physically or mentally because Astrid didn't understand quite yet, "I have to, Astrid. What if I have that Berserker insanity inside me? What if, deep down, I'm just like him?" She snapped before she could feel any guilt about it, but apparently she didn't need any guilt at all, because Astrid put soft, comforting hands on her shoulders to soothe them and joked about throwing her into a volcano if that were anything close to the truth.

It made Heather chuckle, it lightened her mood and reminded her that while Astrid may not understand, she'd always get it. "So, let's talk about something less depressing," she said, wanting the mirth to last just a little bit longer, "how about Hiccup?" she suggested, quickly tossing her axe to Astrid and wasn't surprised to find her fumbling with it a bit, surely she'd taken her friend by surprise. But it seemed like that was the wrong thing to say because Astrid didn't say anything back, she just looked toward the ground with her eyebrows furrowed in an emotion Heather couldn't quite read.

"What's wrong?" She asked, stepping forward in concern, did something happen? Astrid looked up to meet Heather's eyes, she seemed to be searching for something, "I'll just go out and admit it, I think I… used to like Hiccup," she told her, but she sounded unsure and cautious. "Used to?" Heather pressed, stepping a tad bit closer, Astrid looked up again, "I don't know anymore, I keep hearing all these things about what a couple should be, what being 'in love' feels like, and I do feel some of those things… I think. But there are others that don't… appeal to me… if that makes sense?" It was Astrid's turn to grip the axe like a lifeline, "Astrid, you do know that you don't have to fit into any molds right? There's nothing out there saying with absolute certainty what a couple should look or even be like."

"I know… but it just doesn't feel right?" Maybe this time it was Heather who didn't quite understand, but she could get it, for Astrid. "If you don't think he's the right one then you are under no obligation to be with him. Ever," she told her, plain and simple and placed a hand on the axe that Astrid clung to so close to her chest.

°•○●○●○●○●○●○● ◇ ●○●○●○●○●○●○•°

Hiccup was back in his hut and about to bang his head against the wall. He's obviously written to Jack before, just because he was asking more personal questions shouldn't make too much of a difference, right? But that's the thing, it was Jack, and for some ungodly reason he held very high and specific standards when it came to the foreigner. He groaned again, crumpling up the millionth letter as he threw it towards some random direction behind him. The sound of Toothless destroying the evidence via weak blast had become so familiar he might start hearing it in his sleep at random intervals. At this point they might run out of paper.

Gods what would he even ask about? Was there a topic that wouldn't breach some sort of line? The rule 'no questions' came to mind and Hiccup cringed, the only things he could think to ask about were only stuff he assumed about Jack, and those were just theories, and that was a disaster he needed to avoid. How would he even ask that? Hey, just a question, are you that one vigilante called Vorder that you probably don't even know about in the first place? He cringed again.

He didn't know how to feel about that one. He knew Jack spoke some sort of foreign language and if he had to guess, the random words of frustration coming from Vorder were also a foreign language. Put two and two together and Hiccup would bet money they were the same thing. Then there was the fact that Jack didn't even blink when Hiccup first mentioned he rode a dragon. Vorder also happened to ride a dragon and he's seen Hiccup riding Toothless multiple times. Not only that but if Vorder had friends who also rode dragons, it would explain how Jack survived. Finally, Hiccup could swear up and down that it wasn't a coincidence that they just happened to be on the same island at the same time. The only question keeping Hiccup from immediately writing it off as true was, why didn't Jack tell him? Sure, he could be a spy but it didn't feel right. Pretty lousy strategy to just happen to be on the same island as your persona. His thoughts were painfully interrupted by his door being slammed open with no sense of privacy whatsoever, though that was pretty normal for the Archipelago, who needed privacy?

"Hiccup, we have more Nadders coming in!"

He refrained from the urge to groan.

°•○●○●○●○●○●○● ◇ ●○●○●○●○●○●○•°

When he finally got to the Stables the first thing he heard was what seemed to be the tail end of a conversation, "...I knew this wasn't such a good idea."

Uh-oh, what happened now?

"Uh, what wasn't a good idea?" He asked, entering the Stables, "Meatlug just went after Windshear," Fishlegs explained.

"And it was awesome. I mean–

"But, is Meatlug okay? Can she fly?" He interrupted, "Yeah, she's fine. Why?"

"Let me guess. More Nadders?" Snotlout guessed correctly.

He quickly turned to Heather, "Heather, we could really use you. This is a big flock that's coming in," he said, hoping that she would agree to come along, "I don't think that Windshear can–

"Windshear will be fine. We'll keep an eye on her," he reassured her. He figured Windshear was just tired or not quite adjusted yet, he was sure it would go well.

It in fact, did not go well. Heather was forced to fly back to the Edge in order to figure out why her dragon was not only growling at the Nadders but shooting at the twins. Hiccup would have argued that dragons– even their own –shooting at the twins was pretty normal but he didn't think that would help much at all so when he landed he instead opened with, "so, uh, how's she doing?"

"Better," she said, which was evident through the way Windshear greeted Toothless, friendly. "She seems better," he told her, Heather did too, though not by a lot. "I just wish I knew what happened," she said, "look, we've flown hundreds of missions. This was Windshear's first one. You should've seen Snotlout when we first started. He couldn't fly ten feet without somehow setting himself on fire," Hiccup told her and as if on cue, here came Snotlout riding on Hookfang, " Did I hear my name? Were you guys talking about me? I know you were. I'm gonna be in my hut. It's got a great view. Come check it out," and just like that he was off. One, two, three, "Hookfang!"

…

"We just need to get Windshear some training. Start with simple flying drills, formations. Get her used to what it's like to work with other dragons," he turned back to Heather and hoped this would be enough to at least get her to try, "I don't know. I think I just need to keep her away from other dragons while we're here," she said solemnly and turned away from Hiccup, "well, now, that's gonna be kind of tough if you become a Dragon Rider," he snuck in, though it was not at all subtle he was kind of running out of options here. "What? Why would I become–

"Heather, that's part of why we asked you here. Just let me work with you guys."

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"You see? Nothing to it," they were flying side by side this time and so far everything had been going surprisingly well, though he'd never say he was surprised to Heather, "let's try a good old-fashioned Wingman formation. Toothless and I are gonna slow down and play the part of Windshear's wingman. We're here for cover if anything comes up beside or behind you," he explained, Heather still hadn't said anything and the air around them was as tense as ever but he had faith that he could make this work. Maybe he just needed some humor.

Hiccup pulled back on Toothless with some strain to station them more behind Windshear rather than right beside her. Heather just stared at them. "Hey," he called nonchalantly, Heather chuckled at this, meaning he was most likely heading in the right direction. Now for phase two, "not bad at all. Alright, your turn. You and Windshear take our wing."

Of course everything decided to go wrong then, measly phase two. She pulled back, and Windshear started protesting like a toddler being dragged away by their parents, "pull back harder," he advised, "I am, believe me," was all she got out before Windshear sped away like a rock in a sling-shot. In turn Toothless only let Hiccup get out a stern, "Toothless, no!" Before also speeding off after Windshear. Not what he wanted.

They sped after Heather and Windshear who swerved any and every direction imaginable, almost hitting them. All the while Hiccup barely registered what was happening because he was too busy trying to get his own dragon under control. At some point Toothless managed to get right beside Windshear and just like that, they were falling. Separately. Because of course he'd fallen off his dragon.

Heather, who was just trying to help, caught him. Also not what he wanted, Gods this was disaster, he thought before jumping off of Windshear at Heather's protest and using the flight suit to get back on his dragon before they hit the water like he'd originally planned. They broke the fall inches from wet demise and he had to strain to help keep them upright. "Come on, bud. You gotta help me out here. Be the bigger dragon," He scolded when they were stable to which Toothless rolled his eyes, Hiccup couldn't really blame him; it was a gesture the dragon had learned from him after all.

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For a moment Jack just stared, his brain not registering– or more like refusing to register –what was happening right in front of him. Sitting on the Quaken with a lazy smile and sleepy eyes was a short blond man. A very recognizable short blond man. He told himself not to get his hopes up, but what else was he supposed to ask? "Sandy?" He questioned, bleeding confirmation that the impossible was truly happening. Of course he knew Sandy finding a dragon and befriending it wasn't impossible. If someone like Jack could do it surely Sandy, the same person who went against Pitch 1v1 and almost won, someone who had one of the wisest hearts Jack had ever seen, could do it easily.

The person– Sandy –nodded their head affirming that yes, this was his friend. Jack almost lost it then and there. After so long in the Archipelago, alone, they'd found each other. A sort of restlessness settled in Jack and he could tell Artemis felt it too because they both started getting slightly twitchy. If his luck was consistent,– and with his luck it probably isn't –then how long until another bad thing happened? He knew it was severely unlikely but the feeling that his skin was too tight around his body never relented so if not for Sandy's safety, then for his own comfort did he motion for his friend to follow him.

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"Hey, where's Fishlegs? Isn't this the second time this week he's missed all the super-fun Nadder herding?" Snotlout complained, rolling his eyes, "he's saying goodbye to Heather," Astrid explained, "this is way harder on him than it is on the rest of us. So cut him some slack," Hiccup added, he honestly didn't exactly know what to do, if he couldn't convince Heather to stay, one of the most open people he knew, how was he supposed to convince Jack to trust him? Someone so secretive wouldn't listen to, "What are you talking about? You fit in great," very convincing Hiccup. "I'm just saying we could use the help," Snotlout countered.

"Yeah, especially with that Dragon Hunter ship coming towards us," Tuffnut pointed out.

"Great," he drawled, spotting said ship.

"They must have figured out what we're doing with the Nadders and decided to head us off."

"It's only one ship. We'll take care of them, no problem," he told them, a plan already forming in his head, too bad life had other ideas. "Uh, I hate to keep bringing down the room, or the, you know, outside, but that isn't exactly the case," Tuffnut argued pointing to three more ships heading their way. "Okay. Guys, let's get above the clouds. We need to regroup," he decided quickly, to which they all obeyed, that is until Snotlout got himself tangled up in what looked to be some sort of wire, "come on, Hookie. It's just a little rope."

"That's not just a rope. Looks like it's made of reinforced steel or iron," Astrid told him, stopping to hover so she could see better, "That's what I said! Come on, Hookie. It's just a little rope made out of some kind of reinforced steel or iron," Snotlout corrected. Meanwhile Hiccup was just trying to figure out what to even do, they could blast the–

"Wait, is that…"

Hiccup looked up at Snotout's confusion to see, "Fishlegs riding–

"Windshear!? What are they doing?" Astrid finished, "doesn't matter. Right now I'm just thankful they decided to show up," he said, because truthfully he really was. Hiccup watched in amazement as the two of them took out Dragon Hunter ships like it was nothing, just the two of them. "Switching dragons was the trick. Now even if there are other dragons around, Windshear is gonna do what comes naturally and protect Heather!"

The rest of the battle went surprisingly smoothly, there weren't any major injuries that needed to be addressed, and it was thrilling to actually be able to fight back. But flying through the nets was a little trick he and Toothless would have to practice more later.

"Dragon Riders, let's clean this mess up, once and for all," as if it was a cue for them, the Riders gained the upper hand easily.

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"Okay, I have to know. Is this a 'goodbye' dinner or a 'welcome-to-the-team dinner?" A familiar voice asked from beside her, "either way, I cannot go back to eating regular food after these delicious chops," Tuffnut said, pretty much inhaling his food like he needed it to survive. Was it a goodbye dinner? No, she supposed not, the idea of staying now that no one was getting hurt seemed too enticing to her. "It's not a goodbye dinner, Fishlegs… I'm staying," Heather smiled up at him as he let out a sigh of relief, "I thank you. And my palate thanks you as well," Tuffnut announced.

"You know, Fishlegs really deserves all the credit."

"Stop, you. You're embarrassing me," he told her, hiding his face.

"Yeah. Stop. Fishlegs? What in the name of Thor could he have possibly done that I couldn't do?" Snotlout asked, and Heather was just about to give him a piece of her mind when Hiccup walked in with fish for the dragons. "If Fishlegs hadn't figured out how to integrate Windshear into our pack–

"Yeah, we'd be back to eating Ruffnut's cooking," Tuffnut interrupted, before catching the Yak chop that his sister threw at him and then promptly began speaking… something.

"Blah, blah, blah. Whatever."

"More yak chops, Snotlout?" Heather asked, purely to get him to shut up but he didn't need to know that. "Yes, please! And can I get some more of those green thingies? They're amazing."

"Beans, Snotlout. They're called beans," Astrid told him as Heather looked on with the first genuine smile she had in a long time. Nothing against Astrid but, this, this is the most welcoming thing to have happened so far, she decided, it was a thought that was interrupted by a Terror Mail.

"I didn't send it," she quickly clarified at everyone's confused glances. They silently watched for a moment as Hiccup opened the letter and read it, his expression tightening with every word. "It's from dagur," he explained and a sort of dread clawed its way from her stomach to her legs making one roll and the other tense. "He's looking for his sister, and he wants our help in finding her," he finished, looking up in concern. No. Never. Not in a million years. She had a lot of time to think lately, about what she wanted, about what Dagur meant to her. Sure, blood runs thicker than water, and Dagur was covered in her father's. She never wanted to see him again and it wasn't even for her own safety, it might as well be for his.

"I knew he'd come looking for me," she spat out bitterly. They had the same stubbornness issues that was for sure, she felt bile rise to her throat just at the thought. She didn't want to spiral into dark thoughts again. She definitely didn't want to vomit in front of her friends, no, her family. A hand was placed on her shoulder for comfort, Astrid, who seemed to notice Heather's potential rabbit hole, stood right beside her. She might as well have been the ground Heather walked on, replacing the unstable earth for something Heather could stand on and stabilize herself. "If Heather doesn't want to be found, then we'll make sure she won't be," Hiccup announced with all the conviction and authority of someone who truly believed it. In turn, Heather believed it.