AN: Hi readers! This fic is going to have a chapter for each month of the characters lives. I will try to have a new chapter every other week. Enjoy!

August:

Hiccup's dad insisted on him going to school in a wheelchair. Ever since he had gotten into the accident that cost him his leg, his dad took every little precaution to make his son safe and comfortable but, most of them just served to aggravate Hiccup. He wheeled himself through the hallway stopping at his shared locker with his best friend, Rapunzel.

She was easy to spot amongst a crowd. Her hair reached down to just past her knees and practically glowed golden. All of Rapunzel's clothes were homemade and had a classic, timeless look to them. Hiccup parked himself in front of her. She shot him an innocent smile.

"Hey, Hic. Excited for our first day as sophomores?" asked Rapunzel as she took books from Hiccup and loaded them into their locker. The brunette shrugged and tossed his hair out of his eyes.

"Eh… I guess. Schedule?" responded the skinny teen. Rapunzel handed him a green slip.

Hiccup took out his own information and compared it. He began with Algebra 2, followed by Honors English, Honors Chemistry, Woodshop, and AP US History, ending with the tragically pathetic Assisted P.E. He sighed just looking at it. Rapunzel started with normal P.E, then Honors English with Hiccup, French, Art, Honors Chemistry, and Honors Math Analysis.

"Whelp, we just have English together. Maybe Merida has something with us," stated Rapunzel. The sporty red head with mismanaged curls approached the pair. She was a recent addition to the group, being exchange student from Scotland. She was to stay for all of high school.

"Hey there, Hics. Hello, love," Merida greeted as she kissed a blushed cheek of the blonde. The girls had been dating for nearly six months now. With this relationship, Hiccup's awkwardness, Rapunzel's hair, and Merida's accent, the friends were major bullying targets. The bell rang, signaling the start of passing period.

"Bye, sweetie. Good luck!" grinned out Rapunzel, giving him two giant thumbs up. Hiccup nodded back, giving as much of a smile as he could and pushing off towards his first period.

Hiccup got two reactions from his peers. One was the look of pity. People would stare with sad looks and give him the occasional empathetic hello. Those who talked to him didn't really talk to him so much as to his stump that he had yet to get a prosthetic for and his chair. To many he had become his condition, not himself. He might prefer the alternative where people just didn't notice him. Since the chair shortened him a lot, he was overlooked, literally and figuratively.

As he continued to Algebra 2, the teen was pushed and shoved and almost got hit by lockers being opened twice. When he finally managed to get to class he went through it as he always has. Bored and just paying attention when most important. Finally he reached the end of the day, Hiccup entered the class he was dreading, Assisted P.E.

He looked around at his fellow classmates, most of them either special needs or majorly handicapped. He shook his head and hung it down. A teacher entered and explained in a simplistic manner that sounded so condescending to Hiccup. He announced the assignments for 'buddies' and Hiccup had been paired with some guy named Jack. The other members of the program entered, meeting their partners. Hiccup looked around for Jack. A mysterious, white haired, pale teen slowly approached.

"Hi, I'm Jack and I'll be," he stopped, sighing with distain on what he had to say, "very special buddy this year." Hiccup almost laughed at how forced the dialogue was.

Giving a shy smile he responded, "Hiccup H. Haddock. It's nice to meet you but I'd prefer not to be called your special buddy, if that's alright." He extended his hand and Jack gave it a firm shake.

"Hiccup H. Haddock? What's the H stand for?" asked the snowy haired boy. Hiccup blushed with embarrassment.

"Horrendous… It's a … a Viking thing. My dad is really into our heritage so . . ." he trailed off, chuckling nervously. Jack smirked, sitting down on the nearby bleachers. Hiccup wheeled closer.

"I actually think that's cool. I'm just Jack Oliver Frost, there's no culture there!" Jack stated loudly, some of the other groups looking at them. Jack seemed not to care, acting as though it was just him and Hiccup.

"So Jack," began Hiccup, "Why are you tutoring in Assisted P.E? It is obviously not by choice."

"My mom thinks it'll look good for colleges. I really could use some filler on my applications. Junior year comes way too fucking fast, I swear," Jack explained. Hiccup swore for a second sadness fluttered on the older teen's features but it was gone right as it came and replaced by a smirk and mischievous brows.

"How about you, Hiccup?" asked Jack. Hiccup raised any eyebrow at the question.

"How about . . . what?" he shot back. The taller boy bit his lip and glanced down at brunette's half of a right leg. Hiccup caught the glance and felt tension rise up inside of himself.

"Oh . . . you mean how my leg. . ." trailed away the freckled boy. Jack immediately regretted touching upon on such a sensitive topic. He frowned.

"I'm sorry. That was really rude," Jack muttered. Hiccup huffed. He was used to being questioned about his missing appendage. Jack was not the first to venture down the road of weird and awkward inquiries.

"It's fine-uh, well I was in a car wreck at the end of my eighth grade year. It was terrible. I was lucky to be alive but my mom," Hiccup completely stopped, losing his composure and feeling his throat tighten and dry up, "didn't have the same luck. The car hit her head on. I just got a lot of debris in my leg with caused the infection that took my leg. So yeah, that's how I ended up here." Hiccup closed his eyes. Every time he went in to any detail on this, Hiccup could barely keep himself from crying. Jack wasn't sure what to do. Even though he had just met the crippled boy, he felt the need to comfort. Tossing away social conventions, Jack wrapped his arms around Hiccup.

Hiccup's eyes opened widely in shock. Apprehensively, the green eyed boy returned the embrace. They must be drawing attention from their classmates again but Hiccup took a page from Jack's book and ignored it.

The two teens continued to talk through the whole class. Hiccup learned that Jack had little sister named Emily, moved here this year and previously resided in Chicago, and loves the cold. Jack found out Hiccup had strong adoration for the fall, plays Skyrim religiously and has Great Dane named Toothless. The bell rang out through the class. Jack offered to go with Hiccup to where his dad was picking him up.

When they arrived at the curb, Rapunzel and Merida were already there.

"Hey guys," said Hiccup. Jack stood quietly on the outside of the group. Rapunzel's eyes darted from Hiccup to the iced blue eyed teen behind him. Merida smirked.

"Who's the hottie?" she said with a wink. Jack retuned her grin. Hiccup blushed and looked at Jack who laughed.

"Jack, this is Rapunzel and Merida," he mumbled. Rapunzel shook his hand.

"Hi! It's so nice to see Hic with new friends. He's not very social," she explained happily. Jack chuckled. Hiccup sent a glare at her.

"Okay thanks, Punz. That's enough humiliation for me today," he stated, puffing out an angered breath. Rapunzel giggled into her hand.

"Alright," she smiled. A giant SUV honked at the four of them. The car belonged to Merida's parents and was currently filled by Merida's mom and her three mentally ill brothers, Harris, Hubert and Hamish.

"That's my mum, then. We will be leavin' you two. Bye Hic. It was nice meeting you, Jack. I know Hiccup will make sure we see more of you," Merida said, grinning mischievously and grabbing Rapunzel's hand to lead her to the car. Rapunzel gave a wave before hopping into the vehicle.

"That Rapunzel got some hair, huh?" stated Jack, simpering at Hiccup. Hiccup smiled back, pushing his hair behind his ears.

"I know they're kind of weird. But they're my best friends," said the green eyed boy.

"Well, I hope I get know them better. And I'm definitely looking forward to getting to know you better," stated Jack as he looked Hiccup up and down. Hiccup felt heat rise to his cheeks and his heart beat quicken. He looked over to his left and saw his dad's beaten up Chevy.

"Um, that's my dad over there so I'll be going," Hiccup told Jack as he glided towards the car. He built up courage in his head and turned back to the pale boy.

"I really like you, Jack. And that's saying something because; it's true, what Rapunzel said. I'm not social at all. But you're different," he rushed out nervously. Jack gave him the biggest smile possible.

"I really like you, Cup," he said happily. Hiccup gave him a look of confusion.

"Cup? What the hell is that?" he asked. Jack slowly stepped closer to his friend, giving him a tempting look with his eyebrows.

"Well, I'm guessing everyone either calls you Hiccup or Hic. If I call you Cup, it will be special," clarified the dyed white haired boy. Hiccup grinned to himself, thinking over the nickname.

"Okay. Bye Jack," he said, returning to his car.

"Bye, Cup!" the blue eyed hunk shouted out as he watched Hiccup's dad help him into the car. Mr. Haddock gave Jack an unsure look as the teen walked down the sidewalk bouncily. He turned his gaze to his son.

"Who's that, Hiccup?" he asked.

"Oh, that's Jack. He's in the P.E program with me. He's nice," responded Hiccup, strapping in.

"Hmm," hummed out his father.

"Hmm? What does that mean?" the deep brunette responded. Mr. Haddock got behind the wheel and stared Hiccup down.

"More than a friend?" asked the gruff, bearded man. Hiccup sighed angrily as he ran his hands through his hair. Since the moment he came out to his dad, every single male he talked to or even looked at was suddenly a boyfriend option. Hiccup liked it better when his dad was ignoring his sexuality.

"Dad, god, no. Is it okay for me to just have male friends?" he responded loudly. Hiccup's father shrugged his shoulders.

"That Jack boy was giving you a look. I know that look; that boy likes you," said the red head.

"Aggh, no," grumbled the wheelchair bound teen. Hiccup would never tell his dad but he had to admit he had a tiny crush on his new friend. And maybe that tiny part was a lie.