Modern AU. So here's a local setting one-shot because I've never done one before, it's usually US or European centric. Also for those who don't know what Grab is, it's the Asian version of Uber.

Hiccup is sure of marrying Astrid, but how can he actually pull it off without help from his friends? (slight OOC)

True to Myself

"Just say from the heart Hiccy, and you could never go wrong." The hoarse voice of Tuffnut Thorston echoed through Hiccup's phone.

"Gee thanks a lot Tuff, very reassuring." Hiccup replied sarcastically to his friend.

It's a rainy Friday afternoon as he just left from work. In the morning, he works as a data analyst for a software company, and in the evening, he's working part time as a ride-sharing driver for Grab. He got on board his black 2014 Honda City to start his duty; typically, he drives around for a couple of hours before heading home.

"I'm serious Haddock, you better ask her ASAP or else she's gonna find herself a new man." Tuffnut continued.

"Yeah right," Hiccup retorted, as he started up his car. "Alright Tuff, I'm going on duty now."

"Good luck with that!" Tuff said before ending the call.

For the past 2 months, Hiccup Haddock had been working up his nerves on how to propose to Astrid Hofferson, his girlfriend of 3 years. He knew that she's the one and he wanted to stay real with his proposal without going too over the top. He also had everything ready, from the engagement ring to the place where he wanted to propose; all he needs to do now is pop the question to Astrid's parents and to Astrid herself. Returning to his drive, his phone rang with a notification, indicating that someone needs a ride. Luckily, the passengers were only located a few blocks back where Hiccup came from, so he made a U-turn and headed towards the mentioned pick-up point.

When he arrived at the pick-up point, he was shocked to see who his passengers were. Anastasia and Martin Hofferson, Astrid's parents, got on board his car and were equally shocked to see their daughter's boyfriend as their driver. Anastasia, better known as Anna, is essentially a mature version of Astrid, who wear her hair in a ponytail. Martin is a stout brunette man about the same height as Hiccup and he's got his left arm fully inked with various tattoos.

"Good evening." Hiccup turned around to greet the Hoffersons.

"Hiccup!" Martin let out a sigh of relief, "Thank Thor you're our ride."

"What do you mean by that?" Hiccup looked perplexed at the statement. He had heard stories of people complaining how some drivers are rough but he hasn't received one yet, at least to his knowledge.

"Oh he had a bad first experience with ride-sharing." Anna replied.

"There were three of us and for some reason, our driver thought I was gonna go to the same place as the other passengers!" her husband ranted. Hiccup had to chuckle at his rant; apparently, Hoffersons tend to act childishly over some petty problems like what Martin had.

"Okay uncle I get it. You won't experience it again, not on my watch." he chortled as they traveled along the traffic congested metro streets.

The rest of the trip went uneventfully, with the Hoffersons sharing some stories of Astrid that are quite embarrassing had she been there with them. Anna shared a memory of a 14 y/o Astrid skinny dipping while Martin told the time she punched a guy for not asking her out to a dance. Hiccup couldn't help but laugh at their stories; its as if he was having a light hearted talk with his friends.

When they arrived at their destination, which is the Hofferson residence, Hiccup thought of asking them for marrying Astrid. So, he left the rear doors locked, hindering them from leaving the vehicle. "What the? Did you lock these Hiccup?" Anna inquired. The auburn haired man turned around to face the couple. Alright, it's now or never. If I get past them, then I'd only have to worry about her. He took a deep breath.

"Before I unlock them doors, I wanna ask you guys for your blessing." Hiccup started, "Because I'm ready to marry your daughter and make her my wife." The Hoffersons gasped at the confession but Hiccup continued.

"Loving Astrid is the best decision I've ever made in my whole life and I can't imagine a world without her." He finished, a crimson blush forming in his cheeks. Martin and Anna looked at Hiccup, then at each other, before uttering a unison "YES!"

"Of course Hiccup, I almost thought you'd never ask!" Anna smiled.

"Well, I love her, and no one can take that away." the auburn haired man replied.

"I would've never asked for a better man for Astrid. You're her first boyfriend after all." Martin added.

"I know uncle, and here's to her being my last love."

"Call me Dad, kid. You're now part of our family and forever you will be." he corrected. "But can you unlock the doors now?" Hiccup chuckled as he unlocked the rear doors, enabling the Hofferson couple to disembark; he also got out of the car only to be enveloped by their embrace. He smiled to himself that he was able to get a yes. One down, now for the final test. He made a mental note to himself. When they pulled out of the embrace, Anna and Martin were quick to drop countless questions on when would Hiccup ask Astrid.

"Do you have a ring already?" Anna prodded further. Hiccup reached for his pocket and showed them the ring, encased in a small red box.

"Oh gods that looks amazing!" Martin remarked. "But still not as great as the ring I gave to Anna." His wife gave him a playful smack to the shoulder as their future son-in-law cherished the sight.

"Thanks." Hiccup blushed, "Looks like I have to get used to calling you Mom and Dad."

A few days later, Hiccup thought this is the perfect time to propose to Astrid. Since they're celebrating their 42nd monthsary dating, he was gonna take her out anyway. He already planned the night: pick her up after work, have a movie date, and head to their romantic spot which is a park on a cliff side known for its amazing night skylines. Its in the latter place where he would get down on one knee and pop the question.

Because it was Hiccup's day off, he had a full day of ride-sharing duty to do, not to mention the myriad of errands he has to finish which are for their date later on. He was distracted throughout the day, thanks to the surge of passengers he had to pick up and drop off and once he called it quits, he drove to his girlfriend's workplace. Hiccup didn't wait long as he saw a blonde woman wearing a blue dress heading towards his car.

Astrid was fresh from a conference meeting, hence the getup. Her free flowing hair draped neatly on her left shoulder, dress accenting her curves in the right places, and she had trouble walking in her 3 inch black heels. Since Hiccup hadn't seen her all day, she was wondering what his reaction might be.

"Hi babe! Happy 42nd!" Astrid got in the car, kissing her boyfriend's lips. Even in simple greetings like this, they always share a kiss and it became a habit.

Hiccup turned to the rear cabin and grabbed a bouquet of sunflowers before giving it to Astrid. "Happy 42nd milady!"

Astrid was surprised by the bouquet; usually, she receives one of these from Hiccup on their anniversaries. Nevertheless, she loved surprises and so she wrapped her arms around her boyfriend's neck and kissed his lips again. Hiccup smiled at the kiss, because he knew that Astrid is still unaware of what's about to happen later the night.

"I love you babe." she pulled out from their kiss, gazing lovingly at Hiccup.

"I love you too." Snapping out of the moment, he asked her about her day at work. "How's the conference?"

"It's alright. But these damn heels are killing me!" she ranted, kicking off her heels. "How does someone endure a full day wearing these?"

"I think you need another foot rub milady, coz them feet are red as cherries." Hiccup commented. He had a knack for massaging his girlfriend's feet, mainly because in her line of work as a secretary, she often wears heels. He unbuckled his seatbelt, gestured Astrid to face his side as she lay her feet on his lap and started rubbing them good. Astrid closed her eyes as she enjoyed the free foot massage courtesy of her boyfriend.

"Oh my gods, that's so good." she moaned. Hiccup rubbed her sore soles before running his fingers in between her toes. Once she was satisfied with the state of her feet, Hiccup got a pair of ballet flats from behind his seat and made Astrid wear those.

"I don't really care what shoes you wear, but I prefer you wearing something that's comfy." he pulled off his signature dorky grin.

"Alright let's go now, you dorky carpool driver." Astrid chuckled before pecking his cheek.

The first place they went was the movie theater at the nearby mall. Astrid picked out the movie, much to Hiccup's dismay; fortunately for him, he ended up liking the movie and wouldn't stop talking about it even as they had dinner. Once they were full, Hiccup drove to the park and parked by the cliff side parking, giving them that romantic view of the night sky. He reclined the front seats and opened the moonroof, revealing a constellation of stars overhead; he knew Astrid had an affinity for the cosmos.

"You know babe, I always loved seeing the night sky, dreaming like a little girl." Astrid sighed, resting her head against Hiccup's shoulder.

"Me too milady." Hiccup agreed. Especially when we're gonna share the same room forever. he added mentally.

They talked about how their respective days came and went until Hiccup realized Astrid was already snoozing in his chest. He lay Astrid's head to the passenger side headrest, hoping that she wouldn't wake up. He brushed her bangs to the side before planting a kiss on her forehead.

"I'll be right back." Hiccup whispered. He got out of the car and went to the other side, where Astrid had fallen asleep. He was nervous, not wanting to ramble but at the same time, he'd feel like an idiot if he didn't propose right then and there.

"Hey Ast?" he gently tapped her thigh to wake her up.

"Mmm?" Astrid wasn't fully awake when she saw a figure kneeling on her right side by the door. That's when her eyes widened at the sight of Hiccup on one knee, holding a beautiful silver ring with a sapphire orb on top, matching her eye color.

"I know this is probably not what you're expecting but if I planned an all out proposal, I knew that wouldn't go to plan." Hiccup chuckled. "So I stayed true to myself because that's why you love me. I've been working the nerve to propose to you for the past two months and this is as real as I can be."

Astrid's heart warmed and her cheeks showing a tint of red, "Hiccup..."

"You said I am your first love, and here I am making you my last romance." Hiccup added. Wait that didn't sound right. he mentally berated himself for that line. "I suck at being cheesy, sorry." he rubbed the back of his neck.

"No it's perfect babe!" Astrid laughed, before reverting to her sincere look. "Go on."

Hiccup took a deep breath before pressing on. "Astrid Hofferson, I am the man I am today because of you. And because of you, I want to spend the rest of my life with you to hold, to kiss, to love, and to carry children." With his free hand, he held Astrid's hand and rubbed his calloused thumb over her ring finger. "Will you marry me?"

This is what Astrid loved about Hiccup; sure he had a tendency to ramble crap but he always speaks from the heart and straightforward. She was giggling like a teenager, tears of joy streaming down her blushing cheeks.

"Yes Hiccup! Oh my gods yes!" She allowed Hiccup to slide the ring to her finger and it looked gorgeous before kissing him passionately. When they pulled out, Hiccup gazed lovingly at his fiancée, so did Astrid.

All it took was for Hiccup to stay true to himself and Astrid will say yes.

A/N: I love to write modern proposal AUs like this since it makes the story flow more realistic, at least in my case. Let me know if you prefer canon verse or modern AUs by leaving a review!