A/N: Thank you all for reading! It's still interesting getting used to writing. Once I have the time to review and edit all this, it should be better. But for now I want to continue the plot and get to the good stuff. You know exactly what I mean.

(Cute stuff. I'm talking about cute stuff. Cuddling. Movie nights. What did your mind go to?)

Cliched note over with. I don't own any movies nor characters in those movies.

Hiccup walked into the art studio with a small grin on his face, still pleasantly surprised about what had just transpired. Waving to Anna as he passed, Hiccup made his way to his normal spot towards the back of the room.

Anna returned Hiccup's wave and noticed this shift in Hiccup's demeanor immediately, feeling a weight lift off of her shoulders. She still fully intended to ask him what happened these past few days, though. It was odd enough to warrant some attention and debriefing on his part.

The class passed as usual, Anna lecturing a bit in the beginning and then letting the students loose to work on their own projects and assignments. She then spent the class walking through the students, inspecting their work and offering feedback or tips when they asked.

Hiccup was currently working on a landscape. An island stood firm against a thrashing, tumultuous sea. A port speckled with Viking ships marked the entrance to a small village filled with sturdy wooden houses sheltering men & women that were sturdier still. He was deep into work when someone tapped him on the shoulder.

"Hiccup, class ends soon." Anna said with a smile, used to having to pull Hiccup from his trance-like work state.

"Thanks Anna." Hiccup smiled back.

Before Hiccup could turn away, Anna said, "Hiccup, I'd like to talk to you after class quick. Do you have time?"

"Oh, uh, sure. I don't have any plans today so that's no problem."

"Great!"

Hiccup cleaned his workspace and stored his painting for next time. He then made his way towards Anna's office where he knocked politely on the open door before entering, grabbing her attention from her computer.

"So, what is it that you want to talk about Anna? Something you need help with?"

"No, nothing like that. I just…. I noticed that you have been down the last few days and I wanted to see what was up. You're looking much happier today, which is great! I just wanted to offer you the space to talk about it if you needed to," Anna said kindly.

Hiccup smiled a little sadly, "So you noticed, huh? Not that surprising I guess. You're probably one of the few people who I am actually close to here… Well. I do feel much better today, like you said. The whole thing I was upset about actually turned out to be a giant misunderstanding that was cleared up right before I came to class, actually," Hiccup explained, skirting the whole 'date' thing.

Hiccup hadn't told Anna about the whole being gay thing yet. He doubted that she cared and actually more expected her to support him fully. He just didn't feel comfortable talking about relationships to anyone. Even Astrid. Although she usually forced it out of him anyways.

"That's good!" Anna lightly cheered with a smile. "So what was this about, if you don't mind me asking?"

It was an innocent question, but it still sent Hiccup spiraling onto a nervous stutter. "Well, uh, it's about this date thing that was supposed to happen then they lost my number and, you know, they couldn't contact me, and it was a mess for a few days," Hiccup rambled, gesturing wildly, "But now they found me and explained it all and its okay, like I said, and… yeah. That's about it," He finished lamely, letting his arms fall to his side.

Anna chuckled to herself about how flustered Hiccup was about this. It reminded her of her own son, how he used to act about dates. She smiled warmly, "Well I'm glad that it all worked out. I hope your date goes well! Do you know where you're going?"

"Actually, I have no idea. We haven't decided yet but I'll tell you about it when it happens."

"Great! I'm looking forward to hearing about him."

Hiccup smiled for a second before he actually processed what Anna said. And it absolutely blew him away. HOW DID SHE KNOW?! Oh gods, what do I do now?! He kept his smile on, but his eyes widened in surprise and mild fear.

Anna laughed out loud at Hiccup's panic. It was a kind and surprised laughter, not a malicious cackle. "Hiccup! Hiccup don't worry. I'm proud of you no matter what, no matter who you date. And you were just avoiding calling your date a 'her' so I took a shot in the dark. If you don't want to talk about it, I totally understand and I'll never mention it to anyone. Okay?"

Hiccup took a big breath and blew it out, sliding his hand through his hair. "Well I guess that cat is out of the bag, huh?" He said with a wry grin. "So, yeah. I'm going on a date with a guy. And thanks for the confidentiality. I'm still working through it myself and don't really want it to be too public."

"Your secret is safe with me, Hiccup. Just one last thing before I let you go."

"What's that? I can't imagine what other secrets of mine you want to uncover," Hiccup smirked.

"Oh hush. I just want to know if he's cute."

He smiled. "Very much so."

"Nice." Anna exclaimed and hi-fived Hiccup.

"I'll see you later Anna," Hiccup said, walking towards the door. He paused, turned, and added "And Anna? Thanks."

"Never a problem Hiccup. Enjoy your date."

Hiccup was out the door when Anna yelled "And don't forget to tell me about it afterwards!"

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Jack was finally able to focus on class for the first day this week. Well, 'focus' is a bit ambiguous here. He could pay attention if he tried, but instead his mind slipped to happy thoughts of a certain auburn haired man and of the possible dates they could have. He didn't necessarily want to do the clichéd dinner and a movie, but if he couldn't come up with anything better, that was the fallback. But Jack was far from relying on the classics. There had to be something that would make for a memorable and great first date. Soon he found himself walking home, texting Hiccup for the first time.

'Hey Hiccup, it's Jack! How did classes go for you?'

"Not the best text ever, but I don't want to start being an absolute goofball right off the bat…" Jack mumbled to himself. His phone buzzed and he immediately checked it.

'Oh they were wonderful as usual. Just a joy. You?'

'Same as you. Though I didn't actually pay attention. I was focusing on our date too much : )'

'If you fail it's not my fault ; )'

Jack grinned at the string of texts, happy to see that Hiccup could still be so sarcastic through text.

'Actually, it would 100% be your fault. You're too cute for your own good.'

'Yeah. Sure. Whatever you say, Jack Frost.' Jack rolled his eyes at Hiccup's response.

'So I've been thinking and have come up with a great date idea. What night do you have free this week?'

'I should be free all weekend. What do you have in mind?'

'Nope! It's a surprise Hiccup! You'll like it, I swear.'

'I don't trust you, Frosty. How do I know you're not going to lead me into the woods and kill me?'

'Frosty? And it would have been your fault for following me into the woods, Hiccey.' Jack sent that one with a particularly evil grin on his face, guessing that Hiccup would NOT like that nickname.

'Call me that again Frosty and you'll have to find someone else to take to the woods to murder.'

"HA!" Jack laughed suddenly. Hiccup was more fun than he thought!

'Oh so you can call me Frosty but I can't call you Hiccey, Hiccey?'

'…'

'I'll pick you up at 8 this Friday. Sound good?'

'I'll be waiting in antici…'

'pation.' "He did not just make a Rocky Horror reference!" Jack spoke to himself.

'I'm looking forward to it. Hiccey. Also, solid reference. I like it.'

'Ugh. Tell me again why it was a good idea to go on a date with you?'

'Cause I'm hot and can make good drinks.' There was a longer pause than usual after this text. Jack knew he was pushing his luck with this whole conversation, but it somehow just felt right.

'Well. I guess I can't say you're wrong.'

"Aah!" Jack half yelled, half screeched in happiness. It was just so fun to tease Hiccup.

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Hiccup's phone buzzed while he sat in the campus library.

'Hey Hiccup, it's Jack! How did classes go for you?'

He read the text from Jack and his heart rate picked up. Welp. Guess I'm not doing homework.

Hiccup gathered his things and called Astrid immediately after leaving the library. He explained the whole situation to her while drafting a response to Jack.

'Oh they were wonderful as usual. Just a joy. You?'

'Same as you. Though I didn't actually pay attention. I was focusing on our date too much : )'

"Oh gods Astrid, he used a smiley. Help."

"He's flirting with you Hiccup. That's what you do when you're going on a date with someone you like. Flirt back!"

"What should I say?! 'Don't fail' or something like that?"

"Well I guess that works. Just add a winking face at the end."

'If you fail it's not my fault ; )'

"God I feel like an idiot Astrid."

"How the hell did you get a date Hiccup."

"Oh I wonder. Maybe it's because my best friend forced me. Wait! He responded."

'Actually, it would 100% be your fault. You're too cute for your own good.'

"Astrid he called me cute. What the fuck do I do?!" Hiccup was veritably panicking.

"Call him cute back Hiccup!"

"Nope. That is a no-can-do. I literally would die."

'Yeah. Sure. Whatever you say, Jack Frost.'

"Really Hiccup? That's what you said? Well at least you were sarcastic about it. That's something, I guess."

'So I've been thinking and have come up with a great date idea. What night do you have free this week?'

Hiccup sighed in relief. Thank the Gods that he changed the subject…

'I should be free all weekend. What do you have in mind?'

'Nope! It's a surprise Hiccup! You'll like it, I swear.'

"Sounds like you're getting laid, Hiccup!" Astrid cheered, teasing her best friend.

Hiccup sputtered, absolutely lost for words for multiple seconds. That CAN'T be what he meant! "I- uh." Hiccup coughs, "I doubt that's what he means."

'I don't trust you Frosty. How do I know you're not going to lead me into the woods and kill me?'

"HA! Good one Hiccup. You're being funny. Very good. Keep doing that." Astrid urged.

'Frosty? And it would have been your fault for following me into the woods, Hiccey.'

"Astrid what the fuck do I do with that. I hate that nickname!"

"He's teasing you Hiccup. Deal with it."

'Call me that again Frosty and you'll have to find someone else to take to the woods to murder.'

"Ooh, you're getting worked up, aren't you Hiccup?"

"Yes. I hate that nickname. And, well, this is kind of fun. Terrifying, but fun."

"That's what I like to hear!"

'Oh so you can call me Frosty but I can't call you Hiccey, Hiccey?'

'…'

'I'll pick you up at 8 this Friday. Sound good?'

'I'll be waiting in antici…

'pation.'

"Do you even need me anymore, Hiccup? You've pretty much got a handle on it at this point."

"Well it's your choice. I think I've got it from here, but who knows what he'll send next."

"Have fun Hiccup!" Astrid said and hung up immediately, knowing full well Hiccup would still need her help. But she also loved to force him to do things he wasn't comfortable with, so this was a perfect chance to do just that.

"Thanks for the support, Astrid," Hiccup mumbled.

'I'm looking forward to it. Hiccey. Also, solid reference. I like it.'

"UuuUUGGHHh!" Hiccup growled loudly in exasperation before smiling. "Well at least he likes Rocky Horror," he mumbled to himself.

'Ugh. Tell me again why it was a good idea to go on a date with you?'

'Cause I'm hot and can make good drinks.'

Hiccup nearly threw his phone. How-What? What do I say?! Astrid! SOS! He tried calling her, but she blocked every one of his calls. Shit shit shit. Guess I'm on my own.

'Well. I guess I can't say you're wrong.'

Hiccup let out a pent-up breath after sending the text. He really is hot though. I just can't bring myself to say it yet…

Hiccup had been heading home through this fantastic mess and just reached his door. Unlocking and opening it, Toothless greeted him with a cheerful meow. Hiccup knelt down to take off his shoe and pet his cat. "What did I get myself into, bud? I can barely talk to people, much less flirt." Toothless just purred and rubbed his head into Hiccup's hand in response. "Oh well…" Hiccup sighed. "Whatever happens, happens. I'll just have to do my best."

Hiccup began preparing himself some dinner, mixing and kneading dough for a pizza. He didn't understand how people could eat cheap frozen pizzas for almost the same cost as an amazing homemade one. Sure, it took a while, but it was so worth it in the end.

He and Jack continued to text casually throughout the night, just chatting about what they were doing and getting to know each other just a little better before their date.

After finishing his cooking and packing away the leftovers, Hiccup set to finishing this evening's homework as well as the work for tomorrow, not wanting to have to think about it either on the date or during the weekend.

Unbeknownst to even Hiccup himself, he wore a smile the entire evening, enjoying himself more than he had in weeks.

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Jack walked into his apartment and immediately connected to the Bluetooth speaker he bought a few months back. He prided himself in that purchase. Turning on his favorite Punk Rock mix, Jack went to his freezer and pulled out a frozen pizza. He threw it in the oven and set it to preheat to the usual 350°. He plopped onto his couch and texted Hiccup until his pizza was done. It being only around 5pm, this was his pre-dinner dinner. "God frozen pizza is good!" He said to nobody in particular while devouring a slice in a few bites.

He worked on his homework a little, but mostly focused on texting his date. He was fun! Jack thoroughly enjoyed talking to Hiccup, though he could sense that the auburn haired man was nervous. Nothing a little fun couldn't solve.

Jack took a last look at his homework and readings before pushing it away, putting it off for later this weekend. He made his way to his room to play some video games and eventually sleep.

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Both boys went through their next day with the date on their mind. Hiccup nervous and excited, Jack mostly just excited. They kept texting and updating each other on their day and classes. Jack discovered Hiccup was an Engineering major with a flair for art, and Hiccup learned Jack was somewhat undecided, but had settled to major in childhood social work.

'I just want to help the kiddos out; you know? I have been through enough in my life to know what it's like and to want to make sure that they are happy, to do everything I can to make their lives better.'

Hiccup wanted to ask Jack what exactly he meant with that, but felt that it was a bit too soon. They hadn't even been on a date yet, after all.

Jack also mentioned how he wanted to minor in music because 'It's just so fun, Hiccup!' Jack claimed to specialize in vocals and guitar, but also mentioned 'I am a badass at everything though, of course. I can just pick an instrument up and be the BEST!'

'Uh huh. Sure. You keep thinking that, Frosty.'

'Oh I don't just think it. I also talk about and do it Hic. I'm a badass, after all.'

'Once again. You keep thinking that, Frosty.'

'You're mean.'

'Yep! Now are you going to tell me where we are going tonight?'

'Absolutely not Hic. You have to be surprised.'

'You're going to kill me Jack. Either from the stress of not knowing or from you actually killing me. Only time will tell.'

'What's with you thinking I'm a murderer? I'm not that scary!'

'Well you are a badass, so I just am being cautious.'

'Hey now, Hiccup. Don't be rude.'

'I'm not being rude. I'm not the one keeping secrets ; )'

'Meanie.'

Hiccup felt a stack of papers lightly swat his head, bringing him away from his phone screen. His Engineering professor stood above him, looking down sternly but kindly.

"Although it is personal worktime now, that does not mean phone time, ya?" The man asked rhetorically in a thick Russian accent.

"Sorry North. It won't happen again."

"Good. Make it be that way, Hiccup." North said before smiling and lumbering away.

Hiccup quickly shot Jack a text before North could see him.

'Just got caught on my phone. Text later.'

Hiccup focused on his work again, doing what he could to purge his mind of the white haired man he would be seeing later that evening.

The day passed quickly and well. Hiccup's excitement for the date that evening continued to grow as the time before it shrunk. He warmed up leftover pizza for dinner and then made his way to his room to get dressed for the date.

That's when Hiccup realized he had no clue how to dress. Grabbing his phone, he texted Jack.

'I know you're being all secretive about the evening, but could you at least tell me how I should dress?'

A few moments later his phone lit up and buzzed.

'Well, clothing is optional, but highly recommended, as always.'

'Jack.'

'Fiiiiine. I won't tell you how to dress, but I'll tell you what I'm wearing. A dark blue sweater and jeans. Also, we will be outside at least for a bit. Happy?'

'And how fancy is said sweater?'

'I have holes cut for my thumbs to stick through, if that says anything.'

'It tells me everything I need to know. Thanks : )'

Hiccup stripped and then re-dressed in his nicest, best fitting pair of jeans as well as a newer green flannel shirt. It was approaching 7:30, so Hiccup made his way to the bathroom to fix his hair as much as possible before Jack headed over. His anxiety was eating away at the back of his mind, telling him that he would mess everything up, but he did his best to just shove it away and focus on anything else. A few minutes later his phone buzzed in his pocket.

'So where do you live, Hic? I'm about ready to come get you.'

Hiccup's heart and stomach both jumped to his throat as he texted Jack his address and did what he could to finish his hair and check himself over one last time. He sighed deeply and made his way to his front door.

He waited for a bit before a white Audi sedan pulled up in front of his apartment.

There's no way he has a car that nice. That can't be him.

'Hey Hiccup! I just pulled up out front, I think. White Audi.'

Hiccup left, locked up, and beelined to the car, getting in the passenger side.

"Hey Hiccup," Jack said a little sheepishly.

"Good to see you Jack," Hiccup said sweetly with a mischievous smirk "Who did you steal the car from?"

"You know, I'm not entirely sure. I just saw it on my way over here and thought 'Hey, wouldn't it look better if I pick Hiccup up in this? The owner will understand' and then got in, the owner left it unlocked so I didn't even have to break in, and hotwired it. So, yeah! Here we are," Jack explained with a casual smile.

Hiccup raised an eyebrow, "Doesn't this mean I'm an accomplice or an accessory to your crime now? I should probably turn you in so I don't go to jail too. I have a cat to take care of."

"Well in that case my whole plan for our night would be ruined. You don't want to be a stick in the mud, do you Hiccup? Cause that would be so lame."

"I'll take my chances." Hiccup said and dramatically turned away from Jack and peered out of the windshield. After a few seconds he sprouted a crooked smile and looked at Jack out of the corner of his eye.

"Well even if you are lame we're still going on this date. So deal with it." Jack said with a smile. "And the real story is that I'm borrowing it from my dad. My family doesn't drive much, so only my mom and dad have a car. When I want to drive somewhere I just have to swing home, grab the keys, and leave a note if they aren't there. So, yeah. Unfortunately, I'm not a master car thief."

He began to drive away from town.

"Okay, that makes sense. I was going to say, this is super nice for a college kid. You would have had to make some serious tips at the bar to get this yourself. Or maybe sell some serious drugs."

"Ha! Yeah. It would have to be drugs since tips aren't that good at the bar."

Hiccup smiled. He was nervous, but so was Jack. That being mutual just made him feel so much better. "So are you finally going to tell me where we're going Frosty?"

"Nope! Like I've been saying. You'll see when we get there!"

Hiccup groaned in false exasperation and stared out at the road, occasionally stealing glances at the guy he was next to. His sweater fit him nicely, defining his chest and arms. It definitely wasn't tight; it just was a cut that suited him very well. The color caused his eyes to stand out even more than usual. And as always, his shockingly white hair stood up in fantastically messy spikes, giving off a bit of a punk vibe that was just somehow so attractive to Hiccup.

"You don't need to sneak, Hiccup. I don't mind if you stare."

Hiccup blushed furiously and immediately snapped his eyes to the road.

Jack just smiled and chuckled. "I would be checking you out too, but that would endanger both our lives. Being dead would make this evening much less fun," He teased.

Hiccup was at a loss, not sure what to say. He settled. "You look very nice Jack. I like your sweater. Makes your eyes bright."

Jack's grin broke into a huge, toothy smile as he continued to look at the road. "Thank you Hiccup. You look very nice as well."

They settled into a comfortable silence for a minute before Jack turned on the radio. They continued to drive into the night towards destinations (un)known.