A/N: This one's based on an original story I wrote 4 or 5 years ago that got discontinued. It was our junior prom, and I wrote the bulk of that story from my personal experience. So this is another local setting modern AU, with the Hiccstrid treatment.

Hiccup is nervous about asking out his crush to the prom. How would he be able to win her over? (Part 1)

How to Get a Prom Date

It was a cool February morning and Hugo "Hiccup" Haddock just got off the bus he takes to school. At the same time, a van stopped behind the bus and Hiccup saw a blonde figure disembark from said van. Immediately, he noticed the figure as 18 y/o Astrid Jane Hofferson, a volleyball varsity player and a student of the science section. Like most of the guys at school, Hiccup is smitten by the blonde, whether it was her smarts, her volleyball skills, or her divine beauty. Funny, Hiccup thought. Her name literally means divine beauty and boy does she look and act like one. He always wondered that a girl like her must have a boyfriend that she's head over heels for.

Contrary to popular belief, Astrid is single and ready to date someone. She never had a boyfriend before and the rumor mill that guys 'made love' with her was nonstop irked Astrid a lot, yet she couldn't do anything to prove them wrong. The downside of being popular. Sometimes, I just want to be a normal high school girl and not feel like a celebrity. She thought as she was walking towards the school gate behind a guy with auburn hair. Astrid noticed the guy from the bus earlier, however she only caught a side glimpse of his face.

I don't remember any classmates that has that hair color, I'll ask Heather. She made a mental note to ask her best friend about this newfound info.

Upon arrival in her classroom, Astrid plopped her backpack on the desk beside her best friend's desk. She looked tired and wanted to end this seemingly long school day; it didn't help that it was a Monday.

"Whoa, someone's not in a cheery mood today." Heather remarked.

"Aren't we all, Heather?" Astrid replied, "With all these 10 hour classes, we'd never find time to buy what to wear for prom!" With the seniors prom happening a week from now, the blonde was adamant in finding an outfit and a date. The latter was just a bonus for Astrid if someone wants to ask her out without it being forced. Maybe I'll go dateless this year. I'm sure the guys I rejected would bad-mouth me to the rest of the seniors. She sighed at the thought.

"Speaking of prom, has anyone bothered you on the way here?"

"Not yet, although I'm worried no one would ask me out anymore."

"That's because you keep on rejecting every guy that asks, Astrid!" one of her classmates retorted. This prompted a round of laughter, and Astrid blushed in embarrassment.

"I'm going with Francis Ingerman, you know, that big blonde guy." Her raven-haired friend smiled.

Astrid smiled meekly. "Oh yeah him. He's a nice catch but I can't understand why he's called Fishlegs."

"Search me, but you should check out his best friend, Ast. I think they call him Hiccup or something."

"What's he like?"

"He's got that auburn hair, about six foot one, lean build, and he's an amputee." Heather described. Astrid suddenly froze; this Hiccup must be the same guy she saw earlier at the bus stop. Damn, he does look hot, but maybe he's already seeing someone.

Meanwhile in the regular section, Hiccup and his friends were talking about how to propose to their prospective dates. Francis Ingerman, who goes by Fishlegs, was bragging about how he landed a date with Heather Watson. Normally, Fishlegs is a soft-spoken guy who doesn't brag that often, but now he's got himself a hot date and wanted to let his friends know.

"Alright bro, how did it go down." Hiccup started.

"It was after our practice yesterday. When you left her to meet up with Tuff, I approached her. We talked for a while, then we headed to the mall to hang out and eat. I just let my guard down, asked her casually, and she said yes." Fishlegs smiled.

"That's it?" Tucson "Tuffnut" Thorston raised an eyebrow. The stocky man nodded.

"Well...I was hoping to give Astrid a shot." Hiccup sighed. At the mention of the blonde woman's name, Hiccup's friends gave him the 'you can't be serious' look. "Oh don't y'all give me that look."

"But Hiccup," Rochelle Thorston, who goes by Ruffnut, interjected, "Astrid's rejected over a dozen guys already. Snotlout's been there thrice!"

"Come on Ruff, don't remind me again." Shane "Snotlout" Jorgenson groaned in annoyance.

"You're just lucky I said yes when you asked me out." Ruff flipped her hair, sending the group into cackles. Hiccup cherished these moments with his gang; despite being a transferee in their sophomore year, the four friends accepted him the moment they heard about the story of his lost left leg.

"Hiccup, whoever you're gonna ask to prom, even if it's Astrid, we'll be there all the way." Tuff placed a hand on Hiccup's shoulder in assurance.

"Thanks guys." Hiccup smiled sincerely at his gang.

*later that day*

After dismissal, Hiccup and the Thorston twins were heading to the lobby when they saw Astrid waiting for someone. From the looks of it, she's either waiting for her friends or a boyfriend. That's when a red 2018 Toyota Altis pulled up in front of them.

"That's a new one. I wonder who's driving?" Ruff commented. Other than Hiccup, she's familiar with the usual cars that park in campus, but this red sedan was a newcomer. Just then, a tall, dark haired man got out of the car and approached Astrid. The two embraced each other, then the man collected her backpack and folders and placed it in the backseat before him and Astrid go in the car.

"Is that..." Hiccup paused.

"Astrid has a boyfriend? And he's not from here?" the twins said in unison. However, Hiccup wasn't buying it. He noticed that if that man were Astrid's beau, they would've shared a kiss, but a hug only? That didn't make sense to him if they were dating. Maybe he's a childhood friend of hers that wanted to meet up. He stuck with that thought.

Afterwards, Hiccup went to the mall to try and find something that would make Astrid's heart melt. He knew she wasn't the typical girl to give roses or chocolates or a stuffed teddy bear, since all of the guys whom she rejected gave her either of those three gifts. After a couple of gift shops passed, Hiccup went to the bookstore to buy some coloring materials and poster boards to write his promposal message.

When he arrived back home, Hiccup got to work on the posters, which was the easy part. Once he was finished, he called his friends to set up the promposal. The auburn haired man wanted a unique approach in asking Astrid out, instead of going all out with the usual stuff. After that being sorted out, Hiccup sighed happily as he lay on his bed. But there was a part of him having second thoughts about this plan: what if Astrid says no? Or what if she's got a secret date? Those questions clouded Hiccup's mind but he shut them out, believing that he should just go with the flow and not assume negatively.

"I hope she's gonna say yes to this."

*next day, dance practice*

"That was her cousin?!" Hiccup wailed at his dance partner.

"Yes Hiccup. Eric and Astrid are really close." Heather said as they were practicing their dance steps. "so you better ask her out soon, or else she's gonna go to the prom dateless and bitter."

"Come on Heather, what chance do I have with someone as popular as Astrid?" Hiccup retorted. The seniors had dance practice for the prom since they are supposed to perform this for the opening act.

"You have the promposal all set, which by the way I love, so why back out now?" Heather riposted. The auburn haired man remained silent. "Hiccup, Astrid's rejecting guys because she wants to feel special, not just some trophy girl to brag about. She wants someone to see her beyond all the accolades and popularity she has."

"I suppose you have a point." The two continued to practice their routine with the rest of the seniors until their dance teacher dismissed them. Hiccup decided to approach Astrid, who was having lunch at the courtside cafeteria.

"Astrid?"

Astrid turned around to the source of the voice. "Oh hey there…Hugo isn't it?"

"Yes, that's me. Just call me Hiccup." Hiccup smiled.

Astrid raised an eyebrow. "Why do they call you that?"

"Because whenever we go out on debuts and there's drinking, I hiccup a lot when I have a bit too much booze." he joked, earning a giggle from the blonde.

The two new friends talked about everything and anything they could talk about. From Hiccup's car accident that caused him to lose his leg, to Astrid's rise to prominence as the school's best volleyball player, they were not afraid of telling each other their personal stories. Although they just met, for Hiccup, it felt like they've been friends for such a long time because of their similarities; the same can be said for Astrid as this is her first time having a lengthy talk with a boy. She didn't have to let her guard up with Hiccup - she can be herself around him.

When it came time for their afternoon classes, Hiccup offered to accompany Astrid to her room. What she doesn't know is that Hiccup planned to ask her out now. As they walked along the side road, a silver Toyota Hiace stopped beside them. Astrid was confused, thinking that someone was going to kidnap her. But Hiccup smirked at her response and so he held her back from throwing punches whoever's going to get off the van.

"Hiccup! Stop that!" she tried to break free, to no avail.

"Calm down Astrid, they're not gonna take us." Hiccup calmly replied.

Before Astrid could reply, four figures got off the van, holding placards and party poppers. Fishlegs and Heather lined up in front of the couple with their placards spelling out 'I'm your knight on your special night, will you be milady at prom?'

"Astrid," Hiccup asked, now facing the blonde. "Would you do the honor of being my prom date?" Astrid could already feel her eyes getting moist at his promposal, and after several no's to other guys, she finally gave in to Hiccup.

"Yes Hiccup!" She gave Hiccup a bear hug and a peck to his cheek. The auburn haired teen felt like he'd won the lottery as he returned the embrace. Tuff and Snotlout opened the party poppers as they cheered for the couple.

A/N: Part 2 coming up shortly! I apologize for the 3 week delay, life's been hectic lately thanks to my job.