Idea: This is a little bit before Astrid and Hiccup became a thing, but it was getting closer and closer to them being official.

This took place before HTTYD2, about maybe 3 years before?

I hope you guys like it and leave some reviews or requests too!


Hiccup laid down on Toothless' back as he glided through the night sky, letting the crispy cool air flow over his torso and run through his now longer hair. He felt two lumps nears the bottom of his scalp where two braids were pressing against the harness. "Astrid .. " he mumbled to himself. He sat up and starting at the braids and was about to take them off when a figure from below rose up to level with him and Toothless.

"And what do you think you're doing?" Said the female voice, in a menacing tone.

"Uh, n-n-nothing Astrid. Just uh, scratching my neck." Hiccup stammered in an uncomfortable tone.

"That's what I thought." Astrid said as she came in closer to Hiccup so her face was visible through the mist and clouds.

Hiccup smiled at her awkwardly, still embarrassed at how she found him and heard him. "So what brings you here? Usually you don't go on night flights anymore ever since you got stable duty."

"Oh, just thought I'd keep an eye on you .. I was hoping we could spend some time together. It's been awhile since it was just me and you." As Astrid said that, Stormfly squawked. Astrid snickered, "And your dragons." She said as she began patting Stormfly near her neck.

Hiccup smiled and stared at this exchange of interaction. He still couldn't believe how a strong, axe-murdering Dragon killer like Astrid could become so soft towards them. Astrid caught Hiccup's smile and stare.

"What're you smiling at?" She asked, with her own smile and her big blue eyes looking up at Hiccup's, meeting his gaze.

"Nothing." He said, with a little laugh as he said it. A few moments of peaceful silence followed. "You want to land?" Hiccup asked, as he looked over at Astrid.

"Yeah, sure." She said, cheerfully. The two of them found a clearing in the forest and they landed together.

They found a good spot near a shallow, but deep enough pond for fish as they sat in the darkness. Toothless curled in behind them and gave them a small fire while also giving them a backrest. Stormfly squatted down and perched herself on a nearby trunk, alert for any suspicious movement. The couple stared at the night sky.

"Isn't it beautiful?" Hiccup said as he looked from star to star. He didn't know much about them, but that they were beautiful.

"Yeah." Astrid breathed in agreement. Hiccup took his eyes from the stars and looked at Astrid. She looked so beautiful. Her blonde hair flowed down her left shoulder in a braid. Her bangs were neatly parted onto her left side, and hung by her ear so that both her blue eyes were visible. She had a lightly tanned leather headband around the crown of her heard. Her blue eyes are what stunned Hiccup the most. They were a kind of shockingly blue that just you and it made him feel like he literally got shocked by a Skrill's lightning and his heart stopped beating. The way they looked at him and the way they curled up when she smi-

"Hiccup?" Astrid asked as he again caught Hiccup staring at her. He had a dazed look on his face and it looked like he wasn't thinking and just day dreaming but he was looking at her. "Hicccuuppp?" Astrid called to him again in a sort of singsong tone with a goofy smile on her face.

"Wha-what?" Hiccup said as he snapped out of his day dreaming.

Astrid laughed at his reaction. "You were looking at me .. again?" Astrid asked, still smiling but Hiccup could sense she was just as uncomfortable as he was.

"Oh, um, sorry." Hiccup said as he blushed.

"Hiccup, is there anything you want to tell me?" Astrid asked calmly

"Uh, no it's, it's uh fine." He said. He was nervous know. He felt like he was burning up, although it was never hot in Berk, or anywhere near here.

"Um, alright." Astrid, still unsure about what was really going on here put her hand on Hiccup's. "Well, if you need anyone to talk to, I'm right here." She said as she curled her hands into his and they intertwined with one another.

"Thanks." Hiccup smiled and nodded his head with appreciation. He really did appreciate it. He felt like she was the only one who really cared, and who really understood. He felt himself gaining some courage again. "Well .. there is something actually .. " He said, you could still here a faint trace of insecurity in his tone.

"What is it?" Astrid asked

"My father," He began, "He keeps bringing up about how I'm going to be chief." He didn't really get too in-depth with it, but he knew Astrid would understand what he really meant, the underlying feeling. She always did.

"Hiccup, you'll make a great chief." Astrid said, staring straight at him, unwavering. "Look at where you are now. You went from being the village idiot, to being the village hero. You showed us the true nature of dragons. You proved to all those vikings there," She said pointing towards the direction of Berk, "That dragons aren't what we thought they were for 300 years."

"I know, I know. But look at my dad has accomplished. The Great Stoick the Vast." Hiccup said as he mimicked a viking accent. "He's so fearless and so powerful, yet so selfless and brave .. " Hiccup went on thinking about all the times his father had to save him from the dragon raids while he just caused mischief around the village.

"I know, we all know Hiccup. But you are too." At this Hiccup looked up to her to meet Astrid's gaze. Feeling she finally got the attention from him she needed, "The Red Death, Hiccup. You were so fearless and brave against it and you defeated her. And selfless Hiccup? You risked your life to save Toothless from your dad. You risked your life to save all of us, including your dad," Astrid trailed off as she lost her courage to go any further. She didn't usually get this embarrassed to say something so simple but it felt harder to accept, "and me .. from the war that could've possibly taken my life."

"I know but" Hiccup was about to start but was cut off by Astrid.

"Hiccup there is no 'but.' You did that, not your father. Not Snotlout. Not me. And for sure not the Twins." At the last part, Hiccup and Astrid both started laughing. "You see Hiccup? You may not see yourself like the way you think people see your dad. But everyone else does." And she put her hand on his arm encouragingly.

"Thanks." Was all he managed to say. A few more moments past.

"Hey, maybe we should start heading back now. It's getting late." Astrid said as she stood up, as well as Hiccup. Toothless sensing the movement stood up and Stormfly walked over to her owner.

"I'll uh .. fly you home." Hiccup said as he and Astrid both mounted their dragons.

"Sounds good." Astrid said with a smile. She liked this idea. She missed the old times where he'd always fly back with her to her home or walk her home from the Mead Hall after village gatherings.

Astrid dropped off Stormfly at the stables in the Dragon Academy and she mounted Toothless with Hiccup and he flew her back to her place. Toothless sensed the two wanted more time than they could have together so he landed a little bit away from her porch, both secretly appreciating Toothless' small but kind gesture.

"So .. maybe I'll see you again tomorrow night?" Hiccup asked, almost hopefully.

"Maybe." Was all Astrid replied. The couple stood awkwardly in front of her porch waiting for the other to make a move, much like waiting for a girls' parents to open the door when she gets dropped off on her first date, but this wasn't the case here since her parents were no longer there, and she was watched over by her grandmother.

As Hiccup turned around to leave, Astrid pulled him back. "Hey Hiccup?"

"Yeah?" He asked as he turned around to face her shocking blue eyes one last time.

She punched him on the shoulder.

"Hey! What was that one for? This time I made sure I didn't do anything wrong!" Hiccup shot back.

"That was for trying to undo the braids I put in your hair," Astrid said staring at Hiccup who smiled sheepishly, "And this .." She said as she hit the back of his head, "Was for not believing in yourself. You're more than qualified to fit the title as chief."

"Okay, maybe you got me ther-" Hiccup said but was again cut off but this time he felt a soft touch graze his lips and it pulled away almost as fast as it came. But when he opened his eyes, her blue eyes were still watching him only centimeters away from his forest green eyes. She leaned in again, this time for a longer kiss. She let go and ran inside, closing the door behind her.

Hiccup looked up at the sky smiling and nodding his head. "Maybe being an idiot sometimes pays off .. " He said as he mounted Toothless.

Astrid shut the door behind her and rested her back against it. She thought about the kiss and how she wished she didn't get so scared when she was around him. A Hofferson never gets scared. As she slowly exhaled and opened her eyes, she as greeted by her grandmother waiting at the table with a single candle lit.

"So you and the chief's son .. " her grandmother joked.

"It's nothing grandmother." Astrid said slightly annoyed as she walked over to kiss her grandmother goodnight on the cheek. She was about to walk up the stairs when her grandmother said, "So when is he coming over for dinner?"

Astrid shook her head, but she also smiled. Her grandmother had a knack for being able to tell when something was up, even when Astrid didn't want to believe it herself. She'd never forget the story her grandmother told her when she wasn't even born yet but her parents tried to arrange a marriage with Snotlout's parents. Her grandmother told her mom, "That would never work. She'll hate him before she even meets him." Her grandmother will her, and the arrangement was cancelled.

Hiccup walked into his home with Toothless following behind him. "Just out for a night flight dad." Hiccup said before his dad turned around but when he did, he was greeted with a weird smile forming across his dad's face who didn't even say anything. "Dad?" Hiccup called to him, quite scared.

"With Astrid right?" Stoick asked his son, still with a creepy smile on his face.

"Dad, drop the smile, please?" Hiccup pleaded who was already plenty grossed out.

"Sorry." His dad said and dropped the smile. "But with Astrid right?" His dad asked again

"Yes dad .. with Astrid." Hiccup said, still confused.

"You like her, no?" His dad asked. "I can see it when you fall in love Hiccup. I know the feelin'." His dad said as he looked up, seeming like he was reminiscing. "She'd make a great mother for your strong heir and my grandchildren." Stoick said as he looked down to where his son was, but Hiccup was already in his room with Toothless.

"I don't like her .. well I do, but not like that." Hiccup said as he paced his room from Toothless' bed to his. Toothless gave Hiccup an, "Are you kidding me?" Look at slapped him with his tail on his back.

"Hey!" Hiccup yelled at his dragon who responded with a small plasma blast, aimed at the top of his bad, barely missing Hiccup's hair. Toothless wore a look that spelled, "Try me." All over it. Hiccup shook his head and went to his bed. He stared up at his ceiling for a little and turned off his light.

"Maybe there really is something .. " Hiccup said before he fell asleep. He dreamed back before there was a Toothless or a "Hiccup the Hero." The way he would look at her, but he'd never once think he'd actually get a real shot at her. She was far too good, far too viking for him. But now, look at him and look at her. They rendezvous secretly together at night, they fly dragons together, they're the closest pair of best friends you'd find on Berk aside from Gobber and Stoick but they weren't a boy and a girl and they weren't teenagers anymore. Maybe deep down, she really did feel the same way for him as he did for her. But he didn't want to get his hopes up too high now.

By the time he woke up, the sun was already peering through his window. He heard a knock at his door and a small soft, yet familiar voice call his name. "Hiccup? Can we talk?" Astrid said as she opened the door slowly to make sure he was awake.