Hiccup stood in front of his bathroom mirror holding a comb and looking highly displeased with himself. It was impossible. Impossible. There was no way he could style his hair without making him look stupid.

He soon decided it was hopeless and gave up.

"Well bud. How do I look?" He said turning to Toothless, who wasn't there.

Hiccup looked in confusion. Toothless had been here a moment ago.

"Bud?" He called.

Hiccup went through the house to search for his dog. As he rounded the corner he heard a crash.

Kitchen, he realized.

That's where the noise had come from and he believed Toothless would be there too.

Sure enough he found his big dog chewing happily on some leaves. In an instant Hiccup's mind seemed to analyze Toothless and the situation before him.

"Leaves? We don't have any plants in the house. Why do they seem so familiar? They look just like the….Oh Crap."

"No Toothless those aren't to be eaten."

Hiccup ran to grab the flowers out of Toothless' teeth.

"Bud these are meant for Merida. At least they were." He said holding the mangled flowers.

Hiccup saw the look Toothless was giving him and realized he didn't mean any harm.

"It's okay." Hiccup rubbed Toothless' head. "I know you didn't mean to eat them."

'Great.' Hiccup thought. 'I hope the flowers aren't a premonition of my date with Merida tonight.'

Hiccup tossed the flowers back on the ground to Toothless. He hadn't even planned on getting Merida flowers, it had actually been Jack's idea.

Hiccup's mind flashed to the conversation he had with Jack the day before.

Flashback

"Okay dude no pressure, but you're going on a date with Merida so you'll need to up your game." Jack said looking at Hiccup.

"I think I'll be fine. Besides she asked me out."

"Yeah, but now you've got to keep her interested."

"We're going to have a picnic in the park, maybe take her to Gobber's workshop since she seemed interested in my gadgets, and then grab a burger and a shake."

"Hiccup, Hiccup, Hiccup." Jack said shaking his head. "Merida's a higher class girl. She's probably use to the finer things, so you've got to play it up. Do things that she would enjoy."

Hiccup was hit with a wind of sudden nervousness. It was obvious that Merida was a little…a lot out of his league. And his track record with girls was…well…nearly nonexistent.

"What do you think I should do?"

"You've got to up your romance, trust me lay it on smooth."

"I don't know Jack. Merida doesn't seem the type to go for that stuff. At least not for a first date."

"Hiccup trust me. Would I steer you wrong?" Jack said with a sly smile.

"Okay then what do you suggest?"

"I call it my 5 Steps To ThePerfect Date Plan."

"You actually named it."

"Shut up it works. 1. Bring her flowers." He said holding up his fingers accordingly.

"2. Take her to a romance movie, where she gets all cozy and snuggles up to you. There's a really big one that came out a few days ago. 3. Take her to a nice restaurant, one that doesn't have a drive thru. 4. Hold her hand while you have a nice walk while feeding her compliments. And 5. Kiss her good night, but not all the lips. Either her forehead or cheek. It'll leave her wanting more. It's a sure fire can't miss kind of date.

End of Flashback

Well the flowers were destroyed and he didn't have time to pick up any new ones, so tonight he was relying on steps 2-5.

(0.0)

Hiccup arrived a couple minutes earlier than scheduled for his date with Merida. They had agreed to meet at the theater. He nervously shuffled his feet as he waited for her to arrive. As the sound of footsteps approached from behind him, he quickly straightened his posture when he saw her.

Her red and wild hair was flowing out and about, and she had a smile on her face. She was wearing a red blouse tucked into a pair of high waist jeans, and had on a pair of ankle boots.

"Hi. I'm not late am I?"

"No I just got here a little early. So should we head in?"

"Alright lead the way." She said with a smile.

"I'll go get the tickets." He said once they got in.

"What movie are we seeing?"

"A love to Remember."

"Oh." Merida said sounding surprised.

"Is something wrong?"

"No."

Hiccup could feel the awkwardness in the air as they walked to the tickets booth. Did he say something wrong, or do something wrong. He had been following Jack's plan so far.

"Two for a love to remember."

Merida had been quiet, and from what he could tell, it was an uncomfortable silence. They were maybe an hour into the movie when a sudden awkwardness hit him. Between the giggling sounds from couples or the echoes of a deep make out, Hiccup wanted to crawl under the seat.

What had he'd brought Merida to? What would she think? She'd think he had only one thing on his mind that's for sure.

And if things couldn't get any more unsettling later on when he reached for the popcorn he also reached in and grabbed Merida's hand pulling it close to him before he realized it was in fact her hand.

"What are you doing?" Merida said alarmed.

"N..no..I wasn't trying anything."

"Could you let go of my hand."

"Sorry." He immediately let go of Merida. "I think I'll go refill the drinks."

Because of the panic and his sheer nervousness he completely forgot about the popcorn resting on his leg. His abrupt desire to leave the room caused the bucket of popcorn to land right into Merida's lap.

"Shoot." Merida said standing up to get the popcorn off her.

"Sorry. Here let me…"

"Don't. Don't…worry about it. I'm gonna head to the bathroom and try to the butter out of my clothes."

Hiccup watched as Merida shuffled her way through the theater seats and walked out the door. In the couple of minutes she was gone the movie was wrapping up for the end credits to roll, and he was feeling horrible.

How could he have spilled popcorn on her? Next was the restaurant, hopefully that would go better.

(0.0)

"Sorry again about you clothes."

Merida had a couple of stains on her shirt and jeans from where the butter of the popcorn had soaked in.

"Its fine, you didn't mean to." Merida said trying to sound reassuring. "It's still early, anything else ya want to do?"

"Want to grab a bite to eat."

"What you'd have in mind."

"There's a nice restaurant up the road called La Fantasia it's an Italian place."

Merida paused and gave a sigh.

"I've heard of it. I've actually been there a couple of times."

'So Jack was right Merida was use to the finer things.' Hiccup thought. 'I chose this place per Jack's recommendation. Since she likes it here maybe it'll go better than the movies."

"My car is right over here." Hiccup said pointing.

"The restaurants not that far a place if you wanted to walk."

'Step 4, holding her hand while taking a walk.' He thought. 'Does it matter that I'm skipping a step. Probably not, I mean there's no guarantee I'll get another shot.'

"Alright."

The night air seemed to ease the air around the two relieving them of any stress. Walking side by side they both couldn't help but smile.

"So Hiccup I've been wondering about that stuff in your car. Who taught you to make things like that, it's really cool."

"Cool? You thought that stuff was cool?"

"Obviously. Don't you?"

"I mean I like it, I just never consider it cool. It was just something I was good at, so I kept doing it. My Uncle Gobber taught me, he thought a hobby would be good for me."

"Uncle Gobber?" Another unusually nickname Merida thought.

"Yeah he's not really my uncle, but just an old family friend. He taught me everything about building and engineering, I work part time at his shop. If you're interested you could come by some time."

"Alright." Merida smiled happily.

"Alright." Hiccup said sporting his goofy grin. "What about you any hobbies?"

"Archery and horse riding."

"That sounds fitting of you."

"You think so. Most people think I should take up more…lady like activities."

"I think you should do whatever makes you happy."

Merida could only find herself smiling at the words Hiccup spoke, getting butterflies all the while.

"So Hiccup, you love dogs, you're artistic and talented, and you're obviously very nice and kind…"

"Okay not that I don't like it, but I'm not that great of a person the way you're making me out to be." Hiccup said shyly.

"This is a date. Your suppose to want me to think you're great."

"Well yeah I obviously want that, but I'm not without faults."

"So are you going to tell me what's wrong with you?" Merida said raising an eyebrow.

"Yes, I mean no. No I'm not going to do that. Who would do that?"

Hiccup wanted to throw his head into a wall. He just didn't want to be built up only for her to be disappointed in the end. But of course he was digging his own grave, and Merida was….was…laughing?

"You're so different." She said between breaths.

"Is that a good thing?"

"I'm definitely not seeing any bad in it. Your different is kind of amazing." Merida said biting her lip.

Merida hadn't meant to say it out loud, but the words had already slipped out and Hiccup could see the faint blush on her cheeks.

"Wait. Does she think I'm amazing? Is this actually going my way?" Hiccup thought. "She seems to be interested in me."

(0.0)

So the 'date' chapter ended up being really long so I had to chop it up into separate chapters (which I shall post later. obvi) I hope you enjoy. I actually really liked writing it. Anyway comment let me know.