*~~~*Jack & Hiccup Imagines & Preferences*~~~*

*~~~*He Asks You Out*~~~*

Hiccup: A few weeks after you and Hiccup had met, you two had become the inseparable duo.  You always practiced dragon training and you regularly had dragon races as well. The more time you two spent together, the more his feelings grew for you and the less courage he got to ask you out.

Little did you know, Toothless and (d/n) had noticed the chemistry between you two and decided to take matters into their own hands.

"Another great flight, as always," you said, smiling as you jumped off of (d/n).

"Yep, it sure was," Hiccup replied, smiling back at you. 

Then commenced an extremely awkward silence as the two of you stared off into space, waiting for the other to say something. Finally, after what seemed like an eternity of silence, you spoke up.

"Well . . . bye!" you said starting to walk away. Hiccup was about to say 'bye' back, when Toothless jumped in front of Hiccup and growled at him. Hiccup sighed before running after you.

"(Y/N)!" he called. You stopped and turned around.

"Uh . . . I was, uh, wondering . .  .if you would . . . uh, um . . . um . . . " Hiccup sighed. To hell with it.

"Would you fancy going on a date with me?" he finally blurted out. Your (e/c) orbs widened, he then realised what he just said.

"I-I-I mean, if you wanted to! I-I-I'm not saying th-that you should, just if you wan--"

"Yes."

"You don't have to if you don't want to, just in case you feel li--wait, what?" Hiccup stared at you in shock.

"Yes," You repeated, giving him a smile.

Jack: "I wonder if he's even coming this evening . . . " you murmured to yourself as you looked out the window.

"Who's 'he'?" asked a familiar voice. You turned around and jumped, seeing the famous winter spirit perched on top of your writing desk.

"You need to stop doing that! You'll give me a heart attack!" you exclaimed, clutching your heart. Jack smirked and placed his feet back onto the ground.

"But I do it all the time. Surely, you must have a heart attack by now?" he said, tilting his head slightly. You sighed in annoyance.

"What d'ya want?" you asked. Jack jumped off of your desk and walked over to you, with an unusual serious look on his pale face.

"Well, it's kinda stupid . . . " he started. You smiled and took his hands in yours.

"Honestly, anything that comes out of your mouth is stupid, really," you remarked. Jack gave you a sarcastic smile.

"Gee, thanks. You always know what to say(!)" he drawled, while you giggled.

"Jaaaaack . . . tell me . . . " You pleaded. Jack sighed.

"Alright, alright, you got me, (y/n)," he gave in. You smiled sweetly at him. Jack always knew how to make you smile.

"Um, well, I've actually wanted to ask you this for a while now . . . " he began.

"Yes?" you encouraged.

"And we've been friends for quite a while now . . . "

"Yees?"

"And, well, you're the only one who really . . . gets me, y'know?" he continued, making you sigh exasperation. Jack always had a knack for stalling when he wanted to tell you something important.

"Jack just come out with it, already!" you urged irritably. Jack took a deep breath.

"Ithinkyou'reareallycoolgirlandIwaswonderingifyouwouldgooutwithme?"He rushed out, causing you to frown in confusion.

"Wait, what?" you asked, incredulous.

"I think you're a really cool girl and I was wondering if you . . . would go out with me?" Jack finally asked, playing with his fingers. You beamed.

"Jack, of course I'll go out with you!" you answered eagerly, taking his hand. "I honestly don't know why you got so scared to ask me." 

Jack shrugged bashfully. "I-I guess I was scared of rejection," he admitted. Your smile widened.

"Don't worry. You'll never have to be scared when you're with me."