After four hours of flying it become evident to Hiccup that Toothless needed a rest. There was a small island just shy of five miles away it seemed, all of half a minute with Toothless at top speed.

"Toothless needs to rest!" Hiccup shouted to Jack. Jack nodded as he followed Hiccup's line of sight to the island and zoomed off in it's direction. After two minutes Hiccup and Toothless reached the island. Hiccup hopped off of Toothless and gave him ten fish to nosh on while he stretched his legs. Toothless quickly finished off the fish, burped out their carcasses and started wading into the water to get more. Jack stood up and followed Hiccup around.

"Uh… can I help you?" Jack's behavior was rather odd to Hiccup. He just shrugged.

"People never see me, it's weird." Hiccup understood on a rather emotional level. For the better part of his life, not even his own father saw him for who he truly was. He knew it must have been worse for Jack. He wanted to change the subject, Jack didn't seem like an entirely open kind of guy.

"Sooo, uh you and Merida huh?" Hiccup asked. He noticed himself doing the 'arm thing' Astrid always teased him about. He wouldn't let his mind go there. He took his eyes off of Jack and stared at Toothless who'd managed to capture twenty more fish to feast on. He watched as the cat-like dragon scorched the ground beneath him and curled up for a nap. Hiccup chuckled a bit, Toothless never changed.

"I don't know. It's complicated." Jack kicked some sand. It reminded him of Sandy, which then reminded him of North and Bunnymund and how he hadn't been making too much trouble for them lately. He'd have to make a note to do that once this whole ordeal was done.

"What's so complicated?" Hiccup threw his hands in the air – the hand thing. "You like her, she obviously likes you. There's nothing complicated about it." Jack smirked. For as wise beyond his years as Hiccup was, he was still incredibly naïve.

"Well I don't grow up, she does. Can you honestly see a thirty year old woman with an immortal kid who most people don't believe in?" Jack asked perching on a rock. Hiccup rubbed the back of his neck. Even when he was insecure, Jack was still fresh as ever and more brooding than Hiccup ever could be. Honestly, Hiccup was intimidated by Jack.

"I guess not. I'm sure you'll figure something out though. Merida is anything but ordinary, and it doesn't seem like she wants anything but adventure." Jack shrugged and look at Hiccup sideways pointing his staff in his direction.

"What about you? You got a girl?" The way Jack spoke was so nonchalant. Sadness tugged at his heart. Hiccup coughed a bit.

"Sort of… I used to." Jack jumped off his rock and punched Hiccup in the arm.

"Ah that's unfortunate, broke up with you did she?" Hiccup glared at Jack.

"Died actually." He didn't see the point in beating around the bush. Jack's face mirrored every sense of the word facepalm.

"Oh. Wow I feel like an ass. I'm really sorry Hiccup." Hiccup walked up to Toothless and patted him on the head. Toothless seemed down, no doubt missing Stormfly. Hiccup threw him five more fish and took a few for himself.

"We'll be alright, right bud?" He cocked his head to look at Toothless who had been not so thrilled with Hiccup for waking him up from his nap. Jack so desperately wanted to offer Hiccup some comfort by telling him about his Mother. How could he even bring that up in conversation though? He didn't even know if she was still alive. For all he knew she could have starved or frozen to death. Plus, Hiccup might take off and leave Jack to find Rapunzel for himself. He knew a dragon could find something that was lost better than he ever could. He couldn't risk it.

"Uh Jack?" Jack whirled around to see Hiccup staring at him quizzically.

"Uh Hiccup?" He repeated. Hiccup stood there awkwardly, a little starstruck (still) and repeated himself.

"I asked if you thought we should get going?" Hiccup motioned towards Toothless who was itching to get back in the air. Since Hiccup became chief there wasn't a ton of time to fly. No one else knew how to fly him either, Astrid always said she would but… well you know.

"Oh right, yeah let's go." Jack didn't feel like flying himself so he hopped onto Toothless with Hiccup and off they went.

Jack watched the world go by as the chill from Berk faded away and a warmer climate came to be. It was still freezing, mind you, but it was bearable. Neither Jack nor Hiccup felt cold though, the cold never bothered them. An hour or so went by and Hiccup didn't utter a word. Jack wasn't in a talking mood. He couldn't stop thinking about Merida and what they were going to do. He was also worried sick about Rapunzel. He kept praying silently to the man in the moon to keep her safe. If she died, he didn't know what he would do. He wouldn't even go there.

All of a sudden Jack looked up and saw a blur of green whiz passed him. Hiccup didn't even blink. He probably couldn't see her. Toothiana never made it to Berk. She turned around and waved to Jack. He gave her a half smile and waved. They'd never spoken, not even once. She hadn't come to Rapunzel's tower either. He wondered what the policies were when it came to whose houses/villages she'd send her tooth faeries. He shrugged, thank goodness he wasn't stuck collecting teeth and watching over kids, that'd drive him nuts.

"Hey Hiccup, do you believe in Santa or the Easter bunny?" He asked. Hiccup turned his head.

"Who?" Jack shrugged, perhaps Hiccup's village hadn't caught up to that time yet. You see, those deemed worthy for immortality by the man in the moon weren't under the restrictions of time that normal humans were. He didn't even know if Bunnymund or the Toothfairy or North existed in Hiccup, Merida and Rapunzel's time. That would explain why Toothiana never came to any of them and why Rapuznel laughed when he tried to explain who Bunnymund was.

"Nevermind." Hiccup shrugged and kept flying. Another three hours went by and Toothless was completely exhausted. It was then that Hiccup recognized the beach he had ended up on that gruesome night. His eyes widened as he took Toothless down towards it.

"What's going on? Does Toothless need another break?" Jack asked. Hiccup took off his flight helmet and hopped off of Toothless, ignoring Jack completely. Any sign of death that had been at the beach had been washed away by the water. He stared out towards the ocean. He thought of Astrid and Stormfly. It was what she wanted, at least now he knew how to visit the place that haunted his nightmares. Being back… it gave Hiccup some peace. He hadn't realized how heavy his heart was until he was back, the closure that she was gone… It lifted some of the weight. Hiccup felt like he could take a deep breath for the first time in what seemed like a lifetime. Jack couldn't get his bearings, he had no idea where they were.

"I dozed off on Toothless while we were flying, I'm going to get a better look and see where we are." Jack took off and didn't return for another half hour. Hiccup dumped the bucket of fish out and took a bite out of a few and let Toothless chow down the rest.

"You're amazing bud." Hiccup put his hand on Toothless' head. Toothless nuzzled against Hiccup. He didn't know exactly where they were but he felt sadness, and saw the sadness in his friend's eyes. Out of nowhere Jack came whizzing back.

"You picked the perfect landing spot!" Jack hit Hiccup on the shoulder.

"Seriously? More hitting? People need to stop with the hitting! I'm going to bruise. I already have one broken arm, can we not make it two?" He rubbed his shoulder. "Why exactly did I pick the perfect landing spot?" He asked.

"We're really close to Rapunzel's tower, even by walking. Which, by the way, I suggest considering no one around here knows they exist. Come on let's go!" Hiccup sighed.

"Even though my legs could use the walking, Toothless is exhausted. And it's nearly dark." Jack jumped up like a little kid.

"Oh come on! We're so close! He can hide in the tower and we can rest there." Hiccup looked at Toothless who was on the verge of sleep.

"Sorry Jack, I really don't think Toothless can make it. He needs to sleep. I really should as well." Hiccup's broken arm had begun to hurt quite a bit, and his other arm could use the rest from flying Toothless. Jack huffed.

"Fine." He settled in a tree and dozed back off to sleep, worried like crazy for Punzel. Please let her be alright Manny. Please.

-Somewhere not too far from the beach-

Rapunzel woke up, this time in a dark stingy place. She heard music and laughter and smelled an awful raw stench of sweat mixed with alcohol. Her shoulder was still in an immense amount of pain. She saw it had been clean and bandaged, though her dress was completely ruined. Damn it. She wanted to cry, she never should have left the tower. Mother was right, I am too weak. Her hand good hand was now chained to a rock, her bad arm was tied in a sling, there was nothing she could do to move. She heard a voice laugh. It wasn't Flynn's.

"Hey girly. You're pretty decent looking." She saw a giant muscular man step out of the shadows. That's what Flynn must have met by dragons… they were monstrous men. He took a stop towards her.

"Stay away from me!" She shouted and spit in his direction, it was all she could muster. The man narrowed his eyes, he wasn't actually going to do anything to her. He'd sooner add murder to his resumé than pedophile. He slapped her.

"You keep your mouth shut. You hear me?" The slap sent Rapunzel's head into a rock, and unconscious she went. Once again into an awful nightmarish sleep her last thought was praying Jack or her Mother would save her. God knows she couldn't save herself. Little did she know Jack was just one town over, with every answer to every question she'd had since she saw the boy on the beach with the beautiful dragon.

Haha what did I tell you lovelies? I'm in a writing mood! Well that's two chapters in one day, you MIGHT get another one tomorrow but I need to plan out the rest of this story, I know exactly where I want it to go I just have to lead it there. Review please! :D