If Jack Frost knew anything about loneliness, it was that no one deserved to experience the sickening and painful feeling that it was. It was darkness. Not just void of light, but pitch black with dread. Dread and misery. It was the emptiness felt in your chest that nothing but companionship could ever fill. It was knowing that, in fact, no one in the world gave a damn about your existence. It was depression, and learning how to mask it. This particular boy had endured this particular feeling his entire life. Well, his entire life as Jack Frost. Three hundred years.

The first time Jackson Overland laid eyes on the wiry frame of Hiccup Haddock III, was surly not coincidentally the first time he had felt his hardened heart skip. The sullen feeling of leaving his home, his family, and his friends, had disappeared the moment he stepped into Berk. Seeing a small teenage boy stumbling around with two large buckets of water, easily twice his weight had caused his heart to go into hyper drive. But he was Jack Frost now. The silly little fish bone, his one true love, was gone.

The winter spirit let out a long sigh as he tightrope walked across the power lines, his shepherd-like staff balanced on his shoulders and outstretched arms. Stars glimmering above his head, beautiful jewels laid against the black of the night, refusing to be washed out by the city lights seen from afar. Now wasn't exactly the time to be dwelling in the past, he decided. What was it now? Over 300 years? The boy chuckled sadly to himself, sitting down on the nearest rooftop and dangling his legs over the side.

Yet… Why shouldn't he dwell on the subject? Jack pondered the thought for a moment. It had been two hundred years of denying the unknown pain in his chest, and he had only just discovered why he felt this way, (Other than the fact that no one could freaking see him, nor even believed in him,) so why not? He lay down and brought a colorful cylinder out of his pocket, slowly raising a hand to open it for one sweet, nearly faded memory. He sighed once again, watching the assortment of colorful patterned diamonds dance across his vision.

"Hey, Jackson!"

The teen lifted his head to the sound of his name, only to receive a face full of snow. He glared in the direction of the corporate, but his expression softened when he spotted the small freckled brunette, not five feet away. The guilty boy looked towards the sky, quickly raising his hands behind his head and side stepping in the opposite direction. Jackson smirked at the amusing scene, and carefully bent down to pick up two fistfuls of snow. Hiccup had his back turned, facing the recently arrived Night Fury (of which Jackson insisted wanted him dead, but Hiccup denied this,) so the mischievous boy tiptoed closer and closer, until-

*SPLASH*

Of course Hiccup had known Jackson would try to pull a counter attack, so he took it upon himself to drench the older male with a bucket of water. The younger leaned against Toothless, hand over his mouth to try and sustain the uncontrollable chuckles daring to erupt.

"Oops." Hiccup smirked, as Jackson held out his arms to shake them slowly, showing how much water had soaked into his shirt. He glared at the small Viking walking towards him, and held the expression as said boy reached over to brush of some of the frost starting to form on Jackson's clothes. "Didn't see you there, Overland."

"You little sh-" His words were muffled by the feeling of soft lips pressed against his. Without a complaint, he wrapped his arms around the smaller boy's waist, and savored the warmth that was Hiccup.

Jack's eyes slowly opened, releasing a stream of tears down his pale face. He brought his knees up to his chest and hugged them tightly, clenching the container in his hands. Slowly, he glanced up at the full moon in the sky and a sad smile crept onto his lips.

"Hey Manny.." his voice cracked, much to his embarrassment, but he continued, "You know that saying, 'It's better to have loved and lost, than never to have loved at all?' Well, Sometimes… I completely disagree. I almost liked it better when I had this cavity in my heart, and never knew what it was. I had always thought it was just my sadness of being unseen. But…" He chuckled softly and shook his head, "When I opened that tooth capsule the second time.. I remembered him.."

"Geeze, what a drama queen. You are aware that you look pretty loony talking to yourself like that, Frost."

Jack jumped to his feet, startled by the sudden second voice, half expecting the Man in the Moon to finally be answering one of his long ramblings. Unfortunately, something a little more irritating had appeared instead. He rolled his eyes dramatically, and turned to face his unexpected company. What appeared to be a teenage girl, sat cross-legged on the same roof as Jack, not two feet behind him. She was dressed in a graphic t-shirt along with a pair of baggy camo pants, and her combat boots seemed dirtied and worn. Piercings dotted her slightly tanned face, giving her a, 'Don't Fuck with me,' vibe. How had he not heard her coming?

"Jesus Pends!" He scowled, making the girl giggle childishly, "There are other ways to get people's attention other than, say, scaring them half to death."

"Well lucky for me, you're not a person, and you can't exactly die." She sighed and stretched out a pair of elegant eagle wings from her back. "You're a Guardian." Her face turned to one of disgust at the word. Jack rolled his eyes again.

"Thanks for reminding me." He walked over and sat down, shoving her arm playfully. She smiled and locked her eyes with his.

"But seriously. I came to make sure you were okay. Tooth said something about-"

"Yeah I'm fine." He answered all too quickly, avoiding the girl's gaze by examining the box he still held. "Just been thinking about…" He trailed off and hung his head. Penda looked over sympathetically.

"Maybe you shouldn't keep opening that thing if it makes you feel like this twenty-four seven."

"But I have to." Jack whispered, "Now it hurts not to remember. Not to know everything about what we were before."

"Well.." Penda pursed her lips. "We all have the will to love. Before you met that boy, you didn't believe that. You thought that you were an exception. Yet you had just enough in you, that when you saw him, everything was instantaneously better, right?"

"Right." The winter spirit murmured.

"So why isn't that enough? I'll tell you why. We are given the freedom to love, but it always, always, comes with a price." Jack scoffed in response to the statement.

"Leave it to you to find a connection with freedom among all of this. Self-centered, much?"

"Hey, freedom has everything to do with love." The girl smiled brightly, "That's why Cupid and I are best friends."

"What!?'" Jack put a hand over his heart. Penda shoved his arm forcefully and smirked.

"Oh shut up. Fine. Second best friend." She giggled at his over dramatically joyed expression. Her's turned serious again. "It'll all turn out. Okay?"

The boy smiled sadly. "Kay. Thanks. Miss Independence."

"What's with the miss?"

"Just seems weird to call you by your full name without making fun of it."

"Fair enough." She shrugged. They both stood, and Jack reached over to pull her in for a tight hug.

"But really, thanks." He muttered into her long black hair.

"Don't mention it, squirt." Penda pulled away and ruffled his hair. "How 'bout we go visit Jamie and the others tomorrow, yeah?"

"Sure!" He exclaimed enthusiastically. Jack's smile grew as he remembered the awesome kids he had met not that long ago. Him and Pends visited them occasionally, but tried to keep it quiet from North and the other Guardians. Heaven knows what rules they were breaking. Then again, what do you expect when you see a guardian of fun along with a spirit of freedom?