Hiccup looked at the time. It was seven thirty. There wasn't many days Hiccup hated, but there was one.

Valentine's Day.

Why did he hate the day? Well, it just never worked in his favor. He had never had a Valentine. He didn't find himself particularly attractive, and apparently neither did anyone else he knew.

But there was someone who had his eye. Unfortunately he would have to see them today. They were in his classes. He would just lust after them, hoping they would never know that he was interested in them. He was just way too awkward.

He grabbed his bag and made his way to the bus stop. He really didn't want to go to school. The whole school was always decked out thanks to Astrid, his longtime friend, and her involvement in the school Event Planning Committee. She was one of those people, even if she was single, who loved Valentine's Day. Hiccup had no idea why. It seemed like the sort of holiday she would hate, but apparently not.

In a way, the fact that she liked Valentine's Day made the day that much worse. Who was he supposed to mope to?

He sat on the bus mid-way, as usual, and looked out the window. It wasn't cold today, but not quite warm. He jolted forward as the bus came to a quick stop. He looked out the window and his eyes bulged.

Oh no! Valentine's Day and this was the 'object of his affections' bus stop.

Jackson Overland-Frost and his little sister ran down to the bus stop, quickly clamoring onto the almost full bus. His sister sat at the front, next to one of her friends and Jack made his way up the aisle and sat next to...

What the hell?

Jackson Overland-Frost, possibly the most attractive person in the world, was sitting next to him, Hiccup Horrendous Haddock III.

NO FUCKING WAY! AND ON VALentine's DAY?

Hiccup's heart beat as the brown-eyed brunette set his bag on the for between his feet, and smiled at Hiccup. "Hey there Hiccup, looking forward to Valentine's Day?"

Hiccup scrunched up his nose "No" he replied, regretting sounding so rude instantly.

"Oh. Yeah. Me neither. It's no fun, huh?"

Hiccup held back a chuckle, but smiled broadly at Jack's change of attitude. "You seemed keen a few seconds ago."

He shrugged. "Just thought you might like Valentine's Day is all."

"Actually, I don't like it at all" Hiccup admitted.

Jack nodded. "I know that feeling. It really isn't fun."

Hiccup nodded.

"Well, since we won't be getting the V or D, we should go out" Jack smiled, trying to be smooth.

Hiccup had to smile to himself. But how could he tell if the brunette was joking or not? Jack had a reputation as a prankster. Jack could easily be bullshitting him. Jack could easily laugh at Hiccup and tell the whole bus Hiccup was a raging homosexual if Hiccup said yes.

"Sorry, I have plans" Hiccup lied, poorly.

Jack sighed."Of course you do."

Hiccup instantly noticed the true disappointment in his voice. He swallowed thickly. "Uh, and by plans I mean having dinner in my bedroom, while watching a movie and trying to keep the cat from eating my microwave meal."

"Actually, your evening sounds pretty great."

"How about you join me?"

Jack smiled. "Really?"

"Yeah. Really."

"Sounds good. I'll catch the bus home with you this afternoon."

Hiccup nodded. He felt his face turn a light pink.

Jack's hand rested on top of his and smiled at him as the bus pulled into school. Jack stood up and disappeared into the crowd.

...

Hiccup spent the whole day at school feeling nauseatingly nervous. What if Jack said something, anything, to their classmates. Hiccup would be the laughing stock. As usual. But for bigger reasons.

"Hiccup!" Astrid called out. "You have been avoiding me" said said, staring at him.

"No, why would I do that?"

"Valentine's Day."

"Ha... I wouldn't avoid you over something as stupid as Valentine's Day."

She raised a brow. "Last year you told your dad you were sick and took the day off."

"I was sick. I went to the doctors and I had food poisoning from the takeout the night before."

"Avoiding me."

He sighed. "Dammit Astrid. Not what it was like."

"So, I guess I'll forgive you. Have you got a Valentine?"

"No" he said, his face turning a nice shade of embarrassed.

"Oh my gods! You do!" she screamed.

A few people who were in the vicinity looked at them, but Astrid didn't care, and continued humiliating her best friend.

"Tell me who it is!"

"Astrid, can you quiet-?"

"I want to know so bad!"

"Can you stop yelling things out?"

"Why didn't you tell me you were going steady with someone?!"

"I'm not-"

"Wait" she looked at him. "You aren't?"

"No."

"But... but you blushed" she pointed her finger accusingly.

"Because I was embarrassed" he emphasized.

"Oh... so... you aren't seeing anyone?"

"Let's just drop it. You know I hate Valentine's Day."

She nodded. "Fine."

They walked past a small Valentine's Day stall. "Feel like surprising anyone?" Astrid smiled.

He looked at the cards, chocolates and roses that could be bought and delivered to your significant others class. Oh how he would love to send one to Jack without him knowing. Something anonymous. Cards were only fifty cents, and if it was anonymous, he would be fine. He smiled. "Yeah... I think I do."

...

Jack wasn't particularly a fan of Valentine's Day. He had no idea why the school made such a big deal out of it. No one paid any attention, all they did was think about fucking their Valentine all day. He rarely partook in the cheesy holiday, but this year... well, he couldn't help but send one of those anonymous cards. Why the hell not? They were just red or pink heart shaped cards, and for fifty cents, it wasn't going to send him into financial bankruptcy.

He swallowed hard, scribbling Hiccup's name into the pre-designed space. He smiled at the all too cliche (obviously) Be my Valentine message in the card (well, he had to pick one that was relevant, right?) He looked at the small Love from at the bottom of the card and he decided that cliches didn't need to end with the cards message. He wrote your valentine. He dropped the fifty cents into the jar and put the letter in an envelope, adding Hiccup's name to it and putting the letter in the bag for its delivery. He smiled, feeling as though he had done a good deed for the day.

Well, he had tried. He wanted to invite Hiccup to the dance, but he knew that there was no way in hell that he would get him to attend. Seeing Hiccup at his house just seemed way more... well, maybe even a little more romantic. He wondered if Hiccup realized what that invite had done to him. All he wanted to do was grab Hiccup's hand and drag him back to either of their houses.

He chewed his lip, taking his usual seat at the back in his class. Hiccup and Astid were among those crowding into the class. He hoped that Hiccup's card got delivered in this class. He wanted to see his reaction when he received it. He was sure it was would unbelievably dorky, just like the guy himself, but in the most freaking adorable way ever.

He chewed on his pen anxiously. Hiccup hadn't attempted to make eye contact with him at all. He didn't blame the guy. Hiccup was too studious to flirt during English, but still...

Their teacher walked in, beginning the talk about whatever-the-hell they were even learning about, when the door to class opened.

"Happy Valentine's Day!" yelled a student Jack didn't recognize, who was escorting a person dressed as a love heart.

"Really?" sighed Mr. Pitchiner, their not-so-impressed English teacher sighed. "Do you have to come into my class?"

"Sir, but Valentine's Day-?"

"Be quick."

The heart-person attempted to reach into the letter bag, but couldn't, so their guide grabbed the letters for the class. "Okay, I have a letter for you, Mr. Pitchiner."

His usually pale face actually managed to turn a little pink. Some of the class chuckled, most knew better. The heart helper passed him his letter, which he opened it, sighing. "Don't get your hopes up class, its just from Toothiana,"

"She sends all the teachers one" said one of the girls at the front of the class. "She is so wonderful."

"I get one every year from her" said Mr. Pitchiner, setting the card on his desk.

"Hiccup?"

Hiccup looked up from his book and stared at the girl. "Me?"

She nodded. "That's what it says."

A few other people looked at Hiccup just as confused as he felt.

Jack grinned. This was what he expected. God Hiccup was just the most adorable thing.

"Jackson?"

His eyes went wide. "I'm here" he said, not managing to sound as cocky as he would like considering he had just received a Valentine's Day card.

The heart attempted to walk to him with the card, but got stuck between the second lot of desks.

"Just get someone to pass it back" the girl said to her heart companion.

The letter finally made its way to Jack and he opened it, smiling.

Dear Jackson,

Happy Valentine's Day.

Love from your Valentine.

His heart swelled. He was sure it was from Hiccup. He looked at the back of Hiccup's head, smiling like an idiot. It had to be Hiccup right? The feeling had to be mutual. Would Hiccup have invited him over on Valentine's Day to watch a movie and have dinner (most likely, right?) if he didn't like him.

"Okay, that's everyone, get out of my classroom" said Mr. Pitchiner.

The girl and the heart rushed out.

"Okay, so, we are going to do a practice essay today for the text we have been studying."

Jack no longer cared. He was still so excited about the Valentine's Day card. He could hardly believe that something so simple as a piece of pink paper cut into the shape of a heart and folded in half meant so much to him. He would have to thank Hiccup after class. There was only one class after English before home time. He could hardly believe how great today was.

He decided to not bother with the rest of the lesson. When the bell rang he rushed to see Hiccup, but ended up losing him in the sea of student.

He sighed. He would have to wait until the end of the day.

...

"I can't believe you got a card" Astrid grinned. "Do you know who it was? Are you seeing someone? Be honest with me Hic, I can hardly deal right now!" she grinned.

He rolled his eyes. "If I find out I'll let you know."

She groaned. "You know who it is, don't you?"

"I have an idea"

He was sure that Astrid was about to explode. Her eyes were wide and her mouth dropped.

"Uh, but y'know, could be a wild guess."

"You're awful."

"So are you."

"What?!"

"Seriously, give it a break."

She pouted. "Well, fine. I am guessing I am not seeing you and anonymous card giver at the dance."

"No way in hell. I'll see you Monday."

"Okay, see you" she waved as she walked to her last class.

He walked to his final lesson, physics, and took a seat, excited for the conclusion of school.

...

He looked around for Jack, feeling nervous that he didn't see him. Perhaps Jack was lying. No... Jack caught the bus regardless. Also he would have to let his sister know that he was going to Hiccups's, assuming he still was.

"Hic."

He turned around to see Jack, who smiled at him. "Thank you for the card."

"Well, I guess I have you to thank for mine?"

Jack grinned. "That's right."

Their bus arrived.

"Have you seen my sister? I have to let her know I am going to yours."

"I haven't, sorry."

"I'll see her on the bus" he said, following Hiccup onto the bus and taking a seat next to him.

The bus filled up quickly, and soon enough his sister and her friend sat down.

"I'll be one second" he said before walking to his sister. He crouched next to her seat.

Hiccup couldn't believe it.

Jack was coming to his house.

Jack was going to be in his bedroom.

They were going to be in such a close proximity. He wasn't sure he would be able to keep his hands to himself. But then Jack sat back next to him, still grinning from talking to his little sister, that Hiccup was reminded that Jack was way out of his league. Jack was at least an eight. At least. Hiccup really didn't think he was above a three. Well, three was pushing it. Maybe a strong two. He sighed, looking out the window. He was way in over his head.

"You okay?" Jack asked.

"Huh? Yeah... yeah I'm fine."

"You don't seem fine. Do you want me to maybe come over another day?"

"No" he said a little too quickly. "Sorry" he blushed. "I sounded so desperate."

"No, it's okay. I get it. You don't have to be nervous. I'm pretty much harmless."

Hiccup could hardly bring himself to smile. He was literally a bundle of nerves.

Jack smiled and gripped Hiccup's hand in his. "You'll be fine" he smiled.

Hiccup felt his cheeks heat up. Jack held his hand. Properly. Oh gods.

The bus stopped at Jack's house, his little sister looking around at Jack, who waved, before she smiled and stepped off the bus.

"My sister is the best" he smiled. "You don't have siblings, do you?"

"No. Just me."

He nodded. "Must be quiet at your house."

"Too quiet."

He bit his lip. "Sorry."

"Why?"

"It's your stop" Jack said, standing up.

"I know its my stop. Wait... how did you know that it was mine?"

"My house is like, two blocks down. Don't you think I ever walk?" he laughed, stepping off the bus.

"Huh." He stepped down to the first step, but his foot slipped and he fell right into Jack, who managed to catch him. "Sorry" said Hiccup, practically jumping back.

"You're okay."

"Let's just go inside."

Jack nodded and followed Hiccup inside. "Whoa, you're house feels... very historical."

"Ah-ha, yeah... my dad is a viking. Enthusiast. Its a heritage thing."

"Its so cool." He looked around at the tapestries, swords and shields.

"This is what you do with your time when you lose your wife" Hiccup said, setting his bag on the table.

"I'm sorry."

"Happened when I was little. I don't tend to think about it. Wanna order in pizza?" he said, not wanting to talk about his mom, but not really wanting to be as awkward as he was.

Jack nodded. "Sure. I won a pizza eating competition once."

"Really? You did?"

"What is that supposed to mean? Yeah, anyway, I beat Aster."

"P.E. teacher Aster?"

"Yep."

"Who else was there?"

"I dunno. A bunch of people I haven't seen before. Eating all that pizza was the worst thing ever. I was sick for like, two days. But it didn't kill my love of pizza. Guess what the prize was?"

"Pizza?"

"How did you know? It was an all you could eat session for two. Pretty great if you ask me."

"No shit."

"Took my sister. She had so much fun."

"You two are close."

"Yeah... we are actually. Its something I don't think about, but then I see people who hate their siblings... and I just don't get it." He looked around. "Holy shit, that's your cat?! Its a fucking pony."

"Aww, don't be like that. Toothless is an angel" he said, picking up the full-grown Norwegian Forest cat. "He isn't even that big. Around twenty two pounds."

"Huh, just must be all fur."

"Here, hold him. I have to get his dinner."

"Whoa!" he said, attempting to hold all that cat.

Hiccup chuckled and placed some food out for the large cat.

Jack set him down, his arms not quite enjoying holding all that weight. "You're cat is incredible."

"You aren't wrong. I am glad he likes you."

"Uh... guessing there is an important reason why?"

"If Toothless doesn't like someone, I don't like them either" he joked.

Jack personally wasn't so sure if it was a joke. He chuckled awkwardly and looked at the cat. Well, that cat could easily shred him. He stood closer to Hiccup. "All you have to do is impress my sister. Her favorite candy is Reese's Pieces."

Hiccup laughed. "I'll remember that. Uh, my room is upstairs."

"You gonna show me up?" Jack grinned.

"Yeah, I am."

Jack followed Hiccup upstairs. "Your house is just like stepping into the past. Or a museum. Aww, look at this picture of you as a kid. That's cute."

"Ah, don't look at that wall. Those pictures are awful."

"No they aren't. Hey, is this you and your mom?"

"Yeah, it is."

"And all three of you. That's a really nice picture. How old were you?"

"I think I was... three? Maybe a little younger." He shrugged.

"Sorry. I didn't want to make you uncomfortable."

"Its fine. I... I guess I'm just nervous cause..." he sighed, a blush creeping over his face. "I really like you and you're in my house... and I didn't want you to think that I'm a loser."

Jack sighed, smiling. "You don't have to feel nervous. I like you too" he smiled, leaning up to kiss Hiccup's warm, slightly chapped lips.

Hiccup grinned like an idiot. He couldn't even think of anything to say.

Jack smiled. "So, we were heading to your room" he smiled.

Hiccup nodded. "Y-yeah."

Jack rubbed Hiccup's back. "Sorry. I got a little hasty there."

"No, I enjoyed it. I haven't kissed anyone before" he shrugged.

Jack looked a little sheepish. "But... you and Astrid?"

"Uh, no. We weren't a thing" he chuckled awkwardly. He walked into his room. "Uh... yeah..." Hiccup wasn't going to lie. He had totally forgotten about cleaning his room. Sketches, comic books and novels littered the room. "Sorry about the mess" he apologized.

Jack shrugged. He picked up one of the sketches. "So, you like dragons?"

"Uh, yeah."

He smiled. "I like that you are so..."

"Weird?"

"No-"

"Nerdy?"

"No. I love that you are so you."

Hiccup blushed. "Uh... yeah..."

"Sorry... I hope that didn't offend you."

"No. Takes more than that to offend me" he chuckled.

"But seriously. You're one of those people I have to admire. You don't give a fuck about what people think and you just do what you like. I wish I was more like you."

"I always thought you were like that. Carefree... not caring about other peoples opinions" he shrugged.

Jack smiled. "I think I just over-think everything. Uh, so... what movie where you thinking?"

"Uh, I don't know."

Jack sat down and looked through the movies Hiccup had, picking one. "This is good. Didn't think you'd like this one" he chuckled. He sat on Hiccup's bed. "So, when you order pizza I'll pay, yeah? I mean... its only fair."

"How did you wok that out?" Hiccup asked, sitting next to him.

"Well, I am at your house, and watching you movie-"

"So we should split the cost in half."

"Ooh, that could be romantic."

Hiccup rolled his eyes. "Yeah, so romantic."

Jack shrugged. "I don't know. Thought it was nice."

Hiccup shook his head and pressed play on the remote.

...

It was almost twelve thirty by the time they finished the last movie. It had only taken watching four movies (which ended up being boring for the both of them), two pizzas and a round of some first person shooter game Jack found among the DVDs for them to decide to turn in.

Hiccup almost died when he realized how late it was and that he really, really wanted Jack to stay the night.

"Um... it's late" Hiccup said nervously, trying to sound not so nervous. "I am tired" Hiccup admitted. "So, um..."

"Yeah, I should head home" said Jack. "Thanks for having me over. I had heaps of fun."

"Stay the night" Hiccup squeaked out.

Jack grinned. No. Fucking. Way. Hiccup 'Hotness' Haddock had just asked him to stay the night. He almost fainted. "Yes!"

Hiccup blushed, grinning that awkward, crooked smile that Jack thought was so adorable.

Jack could feel his heart beating. "Um... I don't have any pajamas." That and at home it was usually just wearing a shirt and underwear.

"I can lend you clothes." Hiccup opened a drawer and grabbed a shirt.

"That'll do" said Jack, undressing.

Hiccup was sure he was going to either a) spontaneously combust, or b) have a comically timed nose bleed.

Jack pulled the shirt on and looked at the bed. "Uh... sharing?" he asked, suddenly feeling nervous.

Hiccup nodded. "Yeah... um... only if you want to."

Jack nodded. "So, Valentine's Day ends in half an hour" Jack hinted.

"So?"

"So, am I gonna get the d?" Jack asked playfully, rubbing Hiccup's thigh.

Hiccup brushed Jack's hand away. "Next time" he smirked.

Jack took the news well, lying down and looking at Hiccup with a smile.

Hiccup smiled back. He closed his eyes and leaned over for a kiss, which Jack sat up to meet him, pulling him into a sloppy kiss. Hiccup broke the kiss, running out of air too quickly. "Wow" he blushed.

"That was fun" said Jack. "Wet and-"

"Don't start. You make it sound gross."

"Sorry."

Hiccup chuckled. "Happy Valentine's Day."

"Happy Valentine's Day to you too." He kissed Hiccup's cheek and lay back down. "Sleep well." He curled up a little. It didn't take long for him to fall asleep. Within a few short minutes he was lightly snoring.

Hiccup smiled, closing his eyes.

Perhaps he did like Valentine's Day after all.