Hello, everyone~! Summer vacation's officially on for me and HTTYD 2 is almost upon us. Hopefully, these chapters will be going up faster now, but I'm just going to shut up and let you read Hiccup and Jack's first date. Hope you like it~! :)

It was needless to say that Jack was anxious about tonight. It was his first date ever, after all, and he was terrified that it wouldn't go well. But that didn't stop him from dressing up a little and picking up something to set the mood before he came to pick his date up. He kept a lone rose hidden behind his back as he knocked on the door and heard the inevitable sound of Toothless barking his head off as a response. Even though he was outside in the cool air of winter, Jack could feel the house vibrating with every powerful roar that dog made as he came even closer to the front door.

When the door opened, he saw Hiccup on the other side, doing her best to keep the dog inside but not being very successful "Hey." She greeted, almost grunting from trying to control her giant beast of a dog.

"Hey. Ready to go?" He asked before he was pummeled by her dog. Or, more precisely, pushed over and then got a pair of slobber-soaked hands when the canine smelled the rose behind his back. Maybe that was his stupid imagination, but Toothless was being a bit more welcoming to Jack since his last visit. It could just be he was getting used to seeing him in his territory, but Jack could leave his stupid fantasies to himself for now.

"Toothless!" Hiccup smiled up at Jack awkwardly "Just a sec." The tiny girl took the dog by the collar and dragged him inside with little difficulty. Once he was back inside the house, she kept the animal barricaded inside with one of her legs. Her face flashed with shock, as if she just remembered something important, and she turned her head back and shouted "I'm going now, mom!"

Jack heard Val giggle in the background and practically sing "Okay, have fun Henrika!"

"Okay!" The small brunette responded before carefully closing the front door and re-focusing her attention to her date "Sorry, he's hard to control sometimes."

"He's a dog." Jack commented "They're like that."

Hiccup smiled in agreement and brushed her bangs out of her face "Can we go now?"

"Of course." The older teen beamed, trying his best to dry his hands a bit with the back of his shirt as Hiccup was clearly becoming curious about what he was hiding from her. When they were dry enough, Jack slowly slipped the flower into her view and held it out for her "I uh… got this for you."

"Thank you…" Her voice hinted with surprise as she took the rose from his grasp and smiled at it with the softest expression he'd seen on her yet. It was full of adoration and happiness, almost like no one had ever given her a little flower before. But, for all he knew, no one ever had. She came out of her daze after a moment and flashed a metal smile at him "This is really nice."

"I'm glad you like it. Come on." He jogged down the steps and to his car while Hiccup followed. He went around to the passenger side door and opened it, gesturing inside as he looked back at his date "After you."

A little blush showed up on her cheeks and she looked away from him for a second "Since when did you have a gentlemanly side?" She playfully rebutted.

Jack leaned on the car door and smirked "You'll be surprised how many sides I have." Hiccup climbed inside and he shut the door behind her before trying (and failing) to slide across the hood of the car and getting in the driver's seat.

"Was that you showing off your smooth side or something?" The brunette joked.

"Eh, that side's not really on its game tonight." He replied as he backed out of the driveway "But a lot of others are."

"Ah."

For the first few minutes, the ride was quiet after that. But this wasn't just a five minute drive down to get ice cream; it was bound to get boring if they didn't get into a conversation or something "So," He started "uh, what's up Hiccup?"

"Not much." She replied "There wasn't a lot going on today at the house."

"Really? Not even with Toothless running around?"

"Besides him waking me up this morning, no." Jack heard a little giggle "What about you?"

"Eh," Jack turned onto another street "Ana had class this afternoon so I mostly just hung out with Emma."

"Your parents weren't around on a weekend?" Hiccup questioned.

"That's kind of the norm at my house." The taller teen explained "Mom does all the business stuff for a winter sports place on the other side of town. And she volunteers a lot."

"Do you ever go with her?"

"Sometimes, yeah." Jack made another turn.

"What about your dad?" The freckled girl wondered.

He quietly hissed "Dad's a bit more complicated… he's still around, don't worry about that, but, see, he's a technician and work has him traveling like all the time. He hasn't been home for maybe… four months now?" Jack was even starting to question if that really was how long his dad had been gone. He honestly didn't remember exactly when his old man had left on his latest business trip.

"Do you know when he's coming home?"

"Yeah, he'll be home in two or three weeks."

"Where is he?"

Jack thought for a moment, trying to recall "Australia."

"Fun." Hiccup commented "The continent where everything wants to kill you."

"Pretty much." The older teen chuckled "But that is where I met my friend Eli, so it's got it's pros and cons."

"So you've been there?"

"Yeah, dad dragged the family around sometimes when my sisters and I were younger. Eli and I met there when we were, like, twelve, talked long distance for a few years, and then he practically begged his parents to let him go to high school here so he could 'expand his horizons' or however he put it. But, really, he just wanted to stop talking on the phone and get a chance to pull his senior prank with me." Jack laughed at the thought "It's gonna be the best one to ever hit the school." Hiccup laughed along with him.

Conversation died down some after that, but the two still made comments about things that they'd passed by or what they might want to do once they got to the plaza, which they were getting close to. Jack kept his eyes on the road, but stole a quick glance at Hiccup out of the corner of his eye. She just kept staring out the window or down at the rose he'd given her, fiddling with it in her hands. She looked nervous… was this her first date ever too?

Jack pulled into an empty parking space close to the plaza "Here we are." He stated as he put the car in park and turned it off. He turned to look at Hiccup and was taken aback by what he saw. Those grassy plains in her eyes were alight again, widened in an attempt to take in what was before them. The plaza was receiving a small dusting of snow and it was decked out with pure white Christmas lights on every street lamp and display window. Some snowflakes made out of the same lights were hanging from some of the branches on the trees nearby as well. Jack felt his mouth stretch into a smile as he stared at her without a bit of shame. He hadn't seen it that many times yet, but he loved every time he could catch Hiccup while she was looking at something with so much life in those eyes of hers.

"Wow." Hiccup gaped.

"I thought you said you've been here before?" Jack recalled, playfully smirking at her.

"I have." She confirmed; voice fragile as if she was afraid of breaking their surroundings by the sound of her voice "But never in the winter. It looks so pretty with all the lights set up."

"I know." The white-haired boy agreed "Wanna go see it up close?"

Hiccup's smile spread wider as she nodded and unbuckled her seatbelt, leaving the rose he gave her on the seat. She climbed out of the car and practically skipped to the sidewalk in front of Jack, who was close behind her. When he caught up with her, he took her hand into his, clicked the button on his car keys, and locked the car.

Hiccup glanced around quickly and asked "Where do you wanna go first?"

"Wherever you want." Jack answered.

Hiccup couldn't help but smile at Jack's reply. This was already better than she hoped for. The place was beautiful; all of the lights everywhere were making the falling snow sparkle on its way down to the ground and the idea of the date in general was fun to her. She'd never thought of just wandering around window shopping and maybe grabbing a snack or two along the way. They may have been somewhere Hiccup didn't know well, but it was charming and busy enough to make the plaza feel alive but not overly crowded. And, best of all, Jack seemed like he was genuinely interested in seeing her and doing things that made her happy. It wasn't simple indifference or a lack of interest; Jack's remarks came across as questions asked out of lighthearted curiosity and a genuine desire to learn more about her. And the feeling emanating off of him made Hiccup's stomach flutter in the best way. It made the smile that she wore never want to disappear. And it stayed on her face as the evening progressed.

After a minute or two of debating, she decided that she just wanted to circle around and see what they could find in the plaza. Jack followed her lead, never letting his hand untangle with hers as they wove through groups of people on the sidewalk. They passed an array of decorated window displays, all decked out with a little hint of holiday cheer as if the onlookers really needed another reminder of what time of year it was. Normally, Hiccup didn't pay much attention to these displays. But they caught her attention that night for some reason, as if the fact that she was on a date made the assortments of treats, clothing, and decorations more pleasing to look at. At least they were also something to talk about if there was ever an awkward gap in their conversation.

What started out as harmless window shopping evolved into the couple slipping into every store that they passed and aimlessly wandering the aisles to see what was for sale. The first few stores that they explored mostly sold knick-knacks for the holiday season along with candies and different kinds of expensive popcorn with all different flavors and toppings added to them inside their tins. When they started wandering into clothing shops, though, they started to do more than browse. Hiccup started sifting through racks of sweaters without really thinking until Jack came behind her and asked "See anything you like?"

She turned her neck and saw that he was right behind her, his chin hovering a few inches above her shoulder. Wow, did he have a nice jaw line! "Uh, yeah, kinda." She sputtered "But, uh, there's no way I can afford these things. I mean, look at the prices." The sweater she was holding onto at the moment was priced at sixty-five dollars! The one she was wearing under her coat only cost about twenty…. Maybe less. Hiccup was notorious for going directly to the clearance section whenever she went out looking to buy something.

"Who said we were gonna buy anything?" The taller teen retorted. The two exchanged a look and they seemed to get the same idea, splitting up into two separate directions to gather up clothes that they would try on just for the fun of it. They came back together in front of the changing rooms, in the back of the store, each with arms full of clothing. They each went behind a curtain and talked to each other while they switched out what they were wearing, only coming out to see the other when they were both dressed and ready to show off what they found.

For the most part, Hiccup stuck to the winter sweaters that she loved and different pairs of pants and leggings. But she threw the occasional dress and skirt into the pile just to see Jack's reactions. Her favorite had to be when she came out from behind the curtains wearing a long-sleeved gray dress that was pleated on the skirt and had black patches of cloth that looked like leaves sewn around the collar. He came out at the same time as her wearing a bomber jacket, a very warm-looking scarf, and a light gray beanie with his dark wash jeans. They both stared at each other for a moment before smiling and complimenting their date on how good they looked in those clothes.

This went on for a good hour or so before they ran out things to try on from their piles and decided that soon they'd be asked to either buy something or leave. And, since neither of them had the budget to buy anything in the store… they chose the latter.

After they exited the clothing shop they were inside, Jack noticed a coffee shop a few door down from them. Good thing too, putting on his own private fashion show with Hiccup made him thirsty for something "Come on." He led her to the shop and a sign on the glass door read Now serving: hot and ready hot chocolate. Perfect! "Want something to drink?"

Hiccup noticed the sign and her eyes widened a bit, a crooked-toothed smile appearing "Only if I can put marshmallows in mine."

They entered the building and ordered two cups of hot chocolate, with marshmallows please, and sat down at a table for two by the front window. They both shed their coats again and Jack got a better look at Hiccup's plain purple sweater. It was loose on her, like all of her clothing seemed to be, but he still thought it flattered her. Wow, did purple look good on her. Not as good as green did, but purple was definitely a close second.

Hiccup snagged some mini marshmallows out of their little plastic bag of them and dropped six into her cup, settling to eat the rest of her handful as they were. Jack took some of his own, tossing them into his mouth one at a time, and they were quiet again. It wasn't exactly uncomfortable; Hiccup was probably just pre-occupied with making her drink the way she liked it or something. But Jack still got a little anxious about it. He thought back to Anna's advice and remembered the game that she'd told him about. She told him that it's almost guaranteed to kill the silence if he needed it to, especially on the first few dates. He coughed to gain the brunette's attention "So, wanna play a game?"

"What kind of game?" She questioned.

"A Let's-Get-to-Know-Each-Other game." Jack popped another marshmallow into his mouth.

"How do we play?" Hiccup dipped her finger into her hot chocolate and quickly took it out, waving it off "Hot, hot…" she hissed.

"It's pretty easy." The white-haired teen admitted "But it's fun. We each take a turn asking the other something we've been wanting to know about them. We keep going until one of us runs out of questions or we ask something too personal."

"As in too personal period or too personal for a first date?"

"First date." Jack blew on his cocoa and took a sip, not minding the slight sting the heat caused his mouth "Sound good?" Hiccup nodded "Okay, then. You go first."

"Umm…" The freckled girl's eyes wandered around for a while, as if the walls had a list of questions that she could ask on them. Then again, she might have run out of questions after their conversation in the car… No, there's no way she could only have a few things about him that she was curious about "how badly does my dad scare you?"

It took Jack a few seconds to register the question and, when he did, he got a little nervous "W-well, ya know… he's very, uh… literate in weaponry, and he's the size of a freaking mountain." He tried to laugh it off but saw Hiccup start chewing her lip again, something she seemed to do when she got worried "Yeah, he scares me."

She sighed "I figured. I know he means well, but, gods, he's gotta find some limits. He just doesn't want anyone to think I'm, like, vulnerable or anything. He thinks it's his job to protect me so he scares every guy who talks to me for longer than ten minutes."

"Well, he is your father." Her date pointed out "Protecting their kids is part of the job description, isn't it?"

"Yeah, I know. I just wish he'd trust me a little more, ya know?" He nodded at her complaint "Okay, your turn." Hiccup said before she took another sip of her hot chocolate.

"Okay, um…" Jack tapped his fingers against the tabletop, glancing around quickly before locking his eyes on her again "Why does everyone call you Hiccup? Ya know, besides your parents?"

"Well… this is kind of a stupid story…" She leaned on the tabletop and cracked a small smile "My brother started calling me that when we were little. We used to butt heads a lot, like siblings do, and…" She looked to her side, a slight blush dusting onto her cheeks "I got the hiccups all the time when I was younger. And, most of the time, for no reason. So Scott would make fun of me by saying things like 'When ya gonna stop hiccupping, you little hiccup?' And, cause I was younger than him, I didn't really have a good comeback for awhile." Her smile grew again "When I was about three or four, I started calling him Snot Face because he was, well, a snot to me." Her gaze finally re-met Jack's "They're still a little inside joke between the two of us. I know, it's dumb and all but… that's how it started."

Jack cocked his head to the side and his lips parted slightly in confusion "But what about your friends?"

"They call me Hiccup because I asked them to." She replied "I don't like my first name, plus Hiccup's easier to say than Henrika."

"What's wrong with Henrika?" The older teen curiously asked "I mean… I never met another girl with that name before. It's more original than Jack, anyway. Come on, it's only the name of a bunch of dead guys in movies." He smirked.

Hiccup giggled at the comment before she shrugged "I don't know; I just don't like my name. It sounds like a boy's name, doesn't it?"

"Not really." He stated "I think it's kinda cute." He added with another sly grin. He saw hiccup blush a bit and he reclined in his chair "Your turn."

She took another sip with her free hand and pondered her next question "Um… have you dated anyone before?"

Jack shook his head, white locks flopping into his face "No, never. No one ever really… caught my eye until now." Hiccup blushed again "What about you? Have you dated before?" He downed more of his hot chocolate.

Hiccup seemed to get tense after he asked her that. He was worried she wouldn't answer him, but she did "Yeah, I have."

"Oh, really?" Jack leaned forward in his seat again, his smirk growing "And what number am I?" He wondered playfully.

"Uh, three." She responded, adding after a bit of thought "But one of them hardly counts cause it didn't go anywhere… so, I'd say you're only number two."

Okay, she looked kind of uncomfortable talking about this "Look, you don't have to tell me now if you don't want to. You asked first so I just-"

"Got curious." The brunette finished "I know, it's okay. But… I'd rather not tell you about that adventure on the first date."

The taller teen nodded "I get it." They were quiet for a minute before he piped up again "So, does that mean we're going on another date?"

Hiccup chuckled "I thought the game stopped once we got too personal?"

"Come on, humor me."

She shrugged "I'd say the odds are in your favor."

It was nine-thirty when Jack brought Hiccup back home. He walked her up to the front door again and they hugged each other good-bye. Hiccup told him that she'd had a great time and would definitely like to see him again sometime. He agreed and, when they started to separate, Jack planted a quick kiss on her freckled cheek. She said another flustered good-bye before she went inside the house and left him outside on the porch, probably to spare him another visit with her dad. He couldn't say that he was disappointed by that.

Then, he got back in his car and drove home with a stupid smile on his face. He half-expected to came home to find everyone in their respective bedrooms, since it was a little after ten by the time he finally got in the front door. But he was mistaken.

"Jack~!" Emma sang as she hopped off the couch and ran towards her brother, spreading her arms wide as her crouched down to pull her into a hug "How was your date, huh? How'd it go? Are you gonna go out again?"

Jack couldn't help but laugh at his little sister's eagerness "Hey, slow down, slow down. Stop talking for a minute so I can tell you." They separated and Emma started bouncing on the balls of her feet with a goofy grin on her face "I think it went really well; we had a lot of fun together. And~…" He paused for dramatic effect "we are going out again." Emma squealed, though it was obvious she was trying to keep quiet in case Jack had more to say. "We just don't know when yet; we gotta figure that part out."

Emma hugged him again "Good."

"Why do you suddenly care so much about this, huh Squirt?"

"Because it looks like she makes you happy, Jack." The small brunette answered with a hum "I like seeing you like this."

Jack gently pulled himself out of her arms to walk over to the couch. Emma happily took a seat next to him "Hey, it's not like I was never happy before this or anything."

"I know." His sister shrugged "But still."

It was quiet for a moment before Jack heard his mother talking to someone upstairs. But he didn't hear any replies between her pauses "Who's Mom talking to?"

"Oh, I forgot!" Emma exclaimed "Dad's on the phone with her."

"Really?"

"Yeah! He wanted to talk to you but Mom said you were on a date. And~ I bet now he wants to talk to you even more."

"Okay, Squirt." He ruffled her hair as he stood and headed for the stairs "I'll go check on that."

Jack ascended the stairs and noticed Anna in her room when he started to swing the corner. She noticed him and looked at him expectantly, her pet bird sitting calmly on her shoulder. He simply gave her a thumbs up and a smile, to which she smiled back and quietly applauded, before he moved on down the hall to the master bedroom. The door was slightly ajar and he could hear his mother's chatting more clearly, though it was nothing very notable; just what's been going on at her work.

Jack knocked before entering and her chatter immediately stopped to see who it was. She beamed when she saw her son "Char, Jack just got home. Do you still wanna talk to him?" She put her hand over the receiver and whispered "Your father."

Jack mouthed back "Emma told me."

Mary's attention was regained by her husband's voice on the other end "Yeah, of course. Okay, here he is." She handed the cordless phone to Jack before walking out of the room, probably to give the two some privacy.

"Hey, Dad." He greeted.

"Hey there, Jack." Charles Overland responded "How'd your date go, huh?"

"It went great." He sat down on the edge of the bed and smiled "We agreed to go out again sometime."

"Good for you. So, what's her name?"

Jack just smiled "Henrika."

"Henrika…" His father repeated "Don't think I've heard that one before."

"Neither have I. She's, uh, she's as different as her name anyway."

"I bet."

"So, what's up-?"

"Actually, Jack, I have to get going. There's something important I've been putting off that needs to get done." Charles interrupted "But I had to hear how my son's first date went. I'll call on Christmas and we can catch up then, okay?"

His son exhaled "Yeah, okay."

"Good luck with Henrika. You'll let me meet her sometime, right?"

Jack laughed "Yeah, sure Dad."

"Alright, I'll talk to you later."

"Bye." He hung up and stared down at the phone for a moment. Another phone call cut short, just like always. Oh well, he'd be home soon anyway. Jack left the phone on the bed and went back down the hall, going into his room and shutting the door behind him. He let out a sigh as he fell on his bed, laughing a bit when the mattress squeaked a little under his weight. A great date with Hiccup, a call from Dad… he couldn't have asked for a better night.