Disclaimer: I do not own HTTYD, RoTG or any other character that winds up in this chapter.. Because this chapter is going to have a lot of recognizable characters. The only things I take claim of is my OC's. Which probably only wind up in this chapter.

AN: This chapter includes a lot of character introductions, and very poor attempt at a Scottish accent.

Tangled Up With Cupid

Chapter Five; Blind Dating Troubles

Well, Hiccup hadnt been wrong in thinking something was up when Rapunzel told him to go to The Snuggly Duckling.

He felt very uncomfortable once he stepped inside. The place was packed, mostly with kids he had to guess were around his age. Out of all the people, he could spot a few familiar faces. Sitting at a table, he located Rapunzel and her boyfriend, Flynn. She was watching him, fingers twirling the straw in her cup.

Making his way over, he stopped to stand by their table. Looking up, Rapunzel smiled when her green eyes landed on him. "Hiccup! You made it!"

"Yeah, well, I had nothing better to do." He answered with a shrug.

It wasnt at all a lie either. His mother had forced him out of the house, telling him to 'get out of the house, and hang with real people.'

Where she then unplugged his computer, cutting the quest he'd been doing with Fishleg's short. On the walk, he'd made sure to text the other boy, informing him that no, he didnt die. He was just forced to end his aim to hit 90 on his Warlock to hang out with people in person. Fishleg's seemed unbothered by it. In fact, he agreed with Hiccup's mom.

Flynn looked over to his girlfriend, as if silently asking her a question. Scooting her chair back, the blonde rose from her chair. "Hiccup! I want you to meet someone!"

"Rapunzel, I really just want to hang out with you and Flynn." He moved to sit at their table, but the girl grabbed onto his arm, tugging him away and pulling him past tables.

A red head sat at the table Rapunzel pulled him to, the girl looking up and smiling when she recognized the other girl. Her gaze then turned to Hiccup, raising an eyebrow as Rapunzel pushed him into the seat across from the girl. He recognizes her from school, but her name is unable to come to his head, so he waits for Raounzel to introduce her.

"Hiccup, this is Merida. She moved here from Scottland!"

"Whot kind a name es Heecup?" The girl exclaims in a thick Scottish accent.

Hiccup gives a sigh, tilting his head to narrow his gaze at Rapunzel. The girl bites at her bottom lip innocently, glancing between Hiccup and Merida. Before she can leave or make a comment, another person approaches the table. All three look to see who joined them, Rapunzel smiling and Hiccup relaxing a bit as their eyes rest on Jack Overland.

"Hey guys," he greets with a smile.

"Hey Jack," Hiccup greets, the irritation from Merida's question soothing upon seeing another familiar face.

From his table, Flynn watches the group. He eyes how Rapunzel leads Jack away, the boy aiming another smile at Hiccup before he follows the girl to an empty table. His brown eyes then look back to Hiccup and Merida. Seems maybe the first choice Rapunzel decided on wasn't the best. Merida's arms are crossed, looking away from the boy. Hiccup also isn't looking at her, drumming his fingers on the table.

Maybe Flynn will have to make it.. 5 minutes for those two? Unless they can find something to bond over. His eyes move back to his girlfriend, who's making her way back to him.

"Blondie, I think that one's not going to work." He states, nodding over to Hiccup and Merida.

"We just have to give them time." Is her answer.

Her eyes follow Flynn's, bringing her straw to her lips. She's so busy watching them, she hasn't taken notice to the boy who settles himself down at the table she lead Jack over to. The white haired teen looks up from his phone, raising an eyebrow when he meets this guys eyes.

"Uh, hi?"

"Hey, I'm Hans." The boy introduces himself with a smile, holding his hand out towards Jack.

"Jack."

Jack cautiously takes the hand offered to him, before placing it on the table. He's unsure why this Hans guy has decided to sit himself at the table. Both remain quiet, Jack scanning the building. He see's that Hiccup and Merida seem to not be talking, the girl chewing on a chicken leg while Hiccup looks like he's trying to find some escape.

"Say, you're a good looking guy." Hans starts, resting his elbow on the table.

"Thanks?"

"And trust me, if you were a girl I'd so date you." Hans continues, giving Jack a wink.

Jack's lip gives a twitch, but he waits to see on how this guy is going to end whatever he's saying. Hans leans a little closer, cupping a hand around his mouth.

"Can you tell me if any of these cuties have money?"

Was he.. He was trying to find someone with money? Was this guy broke, or just desperate? Jack leaned back in his seat, looking around. He's pretty some of these people have money, or else why would they be here? But, he figures that's not exactly what Hans is asking. So, he's a gold digger?

"Sorry, but I don't think I can help you." Jack tells him.

Hans seems unsatisfied with Jack's answer, but nods his head. While the white haired teen can't help point a girl out for him, he can still find some use with Jack. He points over to Rapunzel, because she looks like she might come from a rich family. Besides, she's not ugly. Not the prettiest there, but not ugly. He points to her.

"What about her?"

"She has a boyfriend." Jack tells him, rolling his eyes.

"Yeah, well, she's never met me." Hans answers, waggling his eyebrows at Jack.

Jack sighs, "Go for it pal."

"I think I will."

Giving Jack a smile, Hans rises from his seat. Straightening out his jacket, he strides over to Rapunzel. Jack watches in amusement, eyeing the way Hans bows, before sitting himself down at the table. Flynn raises an eyebrow, while Rapunzel smiles at the male. Jack wished he was sitting closer, wanting to hear what Hans might say.

Rapunzel's mouth slowly forms an o shape, while Flynn narrows his eyes. Hans has reached over, taking Rapunzel's hand in his. Before he can bring it to his lips, Jack catches Flynn kicking his foot out, causing the chair to topple back and for Hans to go tumbling to the floor.

Jack's got his hand covering his mouth, holding back his laughter as Hans walks back to his table. "Alright, wasn't my best choice, but there's more then one optional girl in here." Hans tells him.

"Go get 'em tiger." Jack manages to say.

While he doesn't like how Hans is trying to find a girl based on if she has money, he's enjoying the entertainment he gets with the boy getting turned down. Or almost hit by a girl's obvious boyfriend.

Hiccup and Merida haven't stated a conversation at all, and 5 minutes in, Flynn comes to save the freckled boy. Merida doesn't even say anything as Hiccup is escorted out of his seat, and taken to another table where another red head sits. The girl is wearing a cowboy hat, which she tips in greeting as Flynn gestures for Hiccup to sit.

Hoping that an actual conversation will start there, Flynn moves back to his seat. Hiccup licks at his dry lips, green eyes settling on the girl. She gives him a big smile, pressing her elbows on the table and leaning closer.

"Howdy, I'm Jessie."

She has a slight tinge of something in her voice, a hint of an accent, but it's not as strong as Merida's. Also, her whole aura just seems to radiate friendliness. Smiling back at her, Hiccup gets a little more comfortable in his chair.

"I'm Hiccup."

She gives a loud snort, before bringing her hands up to cover her mouth. "Well, that's a - he he - that's an interesting name you got there." She exclaims, trying really hard not to openly laugh at him.

Hiccup gives a one sided smile, nodding his head. It's not awkward anymore, he's rather use by now to people laughing at his name. Besides, his mother told him why they nicknamed him Hiccup, and he's not ashamed of it. It was a nickname gifted to him by his parents, a name his mother use to gently whisper when she'd comfort him after a nightmare. A nickname his father used often when he was a kid as his father taught how to ride a bike.

"Sorry, I shouldn't laugh." Jessie apologizes.

"No, no, it's fine. I'm use to it." Hiccup tells her.

She tilts her head to the side, but nods. She leans back in her seat, stretching her legs out. Flynn and Rapunzel both take notice that Jessie and Hiccup seem to he hitting it off rather well. Much better than trying to set him up with Merida. Though Rapunzel kind of figured that was a small chance of working, from what Merida had told her, her mother made her a dating profile.

And the girl agreed to come to the Snuggly Duckling, but never did she say she'd actually try to get along with any guy that approached her. If Hiccup had approached her at school, she would have been more willing to talk. But, not when her mother was trying to find her possible suitors.

"It's working~!" Rapunzel giggles.

"Sure is babe." Flynn replies.

They turn their attention now to Jack. It almost feels like their watching a tennis match, their eyes always shifting between Jack and Hiccup. Rapunzel gives a gasp, her hand reaching out to grab her boyfriend's arm.

"That's my cousin!" She squeals.

Flynn see's a girl settle herself down at the table where Jack is. She's a pretty thing, and Flynn can see the family resemblance in the girl's face. He's never met her, but Rapunzel has told him a lot about her two cousins. He has to take a guess that this one is Anna, because her appearance matches the description Rapunzel has given him.

It was basically a whim for Anna to come. She'd heard about her cousins plan, and really just came to check it out. But the strange boy's hair reminded her of her sister Elsa, and she found herself hesitating before sitting down at the table he was occupying. He looks up, and her breath is almost taken away by the beautiful blue of his eyes.

"Hey, hi! I'm Anna," she greets, stretching out her arm, only to hit the glass of soda on the table. She gives a gasp as it topples over, the liquid spilling out and over the tabme. "Oh my god! I'm so sorry!"

Jack quickly moves to pick the glass up, reaching to grab a handful of napkins, just as Anna's going to do the same thing. A blush comes to both, before Anna is the first to pull away, allowing him to clean up the soda.

"You sure know how to make a first impression." He teases her.

She gives a small giggle, looking away to brush some hair behind her ear. Once the soda's been cleaned up, Jack settles back down into his chair.

"I'm Jack," he tells her, this time the one to offer his hand.

She manages to take it without hitting the glass cup, swearing she felt a tingle of some sort when her hand touches his. She has to keep from pouting when he let's go, letting her hands settle on her lap. His name sounds familiar, but c'mon, Jack isn't an uncommon name.

. . . .

Snotlout presses his nose against the window, his brown eyes peering inside. He can't find a familiar blonde female, but he does see a lot of other pretty females inside the building. Pushing away from the glass, he looks over to Tuffnut.

"Dude, you were right. The place is packed with chicks." He says with a grin.

"Sweet!" Tuffnut also has a grin on his face.

Ruffnut, standing to the side, rolls her eyes. But she watches the two, intrigued to see what happens next. Snotlout lifts his arm, requesting that the other male smell him. Tuffnut doesn't seem affected by the odor, before opening his mouth wide and blowing his breath into his friends face. Determined that both smell fine, Snotlout approaches the door.

The twins follow closely behind, Tuffnut taking in a deep breath once they step inside. It smells a bit like sweat, but the majority is more the scent of food and a mix of different perfumes or colognes. They spot two empty tables by the back, Tuff and Snot settling into one, Ruff situation herself at the other so she can watch the two.

It's been about an hour since Hiccup arrived here. He had hit it off rather well with Jessie, so he was a little upset when he was pulled away. But the girl gave him her number, telling him he could talk to her anytime. Jack and Anna have also seemed to be getting along. Rapunzel felt bad for seperating the two, but she wanted to introduce Jack to other girls.

She had sat him down with a girl named Ariel, who's hair seemed to be a brighter shade of red then Merida's. The girl turned out to be mute, though it wasn't a problem for him. He had a friend who was mute, so he'd done a lot of research in sign language. She informed him that her name was Ariel, she was a freshmen in college, studying marine biology.

They had been talking about her classes when a tall figure stopped to stand by their table, looking up, Jack's eyes lightened when another familiar face looked down at him.

"Pitch, what are you doing here?" He asked, signing the words on instinct.

Ariel looked up at Pitch, but didn't but into their conversation. The dark haired boy aimed an apologetic smile to the girl, "Sandy told me you'd be here. I was just checking up, making sure you weren't causing a mess."

Jack let his eyes roll, signing something to Ariel. The girl gave a noiseless giggle, her big eyes looking away from Pitch. The man sighed, placing his palm down on the table.

"Jack, my boyfriend is the one to teach you sign language. Obviously, I know what you just told her." He stated.

"Well then, you must have figured out that I wrote that I'm almost 18, and I don't need to be babysat by my friend's boyfriend."

Pitch gave a sign, signing to Ariel to keep a close eye on Jack, before he departed from the two. Ariel smiled, not upset at all that they had been distracted. Rapunzel had been a little nervous when she watched Pitch and Jack's interaction, and slumped back in relief when things didn't seem to get hectic.

"I was a little worried they were going to right over Ariel." She tells Flynn.

"Well, I'd be a little more worried about Hiccup."

Rapunzel follows Flynn's gave. It seemed Hiccup had been in the middle of a conversation with a girl named Belle, when a red haired male stopped to stand by the table. He was leaning a little over it, his gaze settled on Hiccup, his upper body blocking Hiccup from seeing the girl sitting across from him.

"This might be a little bad." Rapunzel mutters.

The couple climb out of their seats, moving over to the table. Jack looks up from where he's sitting, eyes following his friends to where Hiccup is sitting. He can see the way Hiccup seems disinterested in the boy who's pushing into his personal space. The dark haired female sitting there is trying to get him to go, but he seems too focused on Hiccup to even listen.

'I'll be right back' Jack signs to Ariel.

The girl nods, watching him as he stumbles out of his seat, rushing over to the table. Flynn has placed himself to stand next to Hiccup, arms crossed as he stares this guy in the face. Meanwhile, Rapunzel has moved to stand next to Belle.

"Listen, guys. This is between me and fishbone here, you guys can go." The boys says, sending a wink to Hiccup.

"Yeah, well, this 'fishbone' doesn't even know you." Flynn claims.

"He will soon enough."

"Sorry, he's taken."

Everyone glances to Jack, who moves to stand on Hiccup's other side. He slings his arm around the other teens shoulders, leaning close so that his lips can brush against Hiccup's earlobe. Hiccup's face is bright red, but he doesn't push Jack off.

"Play along." Jack whispers.

Hiccup takes a hard swallow, but is relieved when the attention moves off him. The red head's eyes are narrowed at Jack, as if waiting for him to drop dead from the look. With a groan, the male stands straight.

"Fine. But just remember cutie," his eyes shift back to land on Hiccup. "When he dumps you, I'll need a lot of boot kissing to reconsider allowing you to be my boyfriend."

He lifts his foot, showing off the dark brown boot he's wearing. He grins at Hiccup, bringing shivers to the boys back, before stalking off to find something else to entertain him.

"Well, that was unexpected." Belle states.

"No kidding," Hiccup agrees with her.

"Looks like your stuck dating me until that guy wants you back."

A blush comes to Hiccup's face at Jack's words, before he shrugs his arm off his shoulders. Jack smiles, stepping back to give Hiccup some space. He can still remember his smell though, an unfamiliar, yet interesting cologne. His lips feel a little fuzzy too, as if numb after going to the dentist.

A kind of late Valentine's gift. I had a few planned that I wanted to post.. But I ended up getting distracted. But, here it is~! Enjoy, if you have any questions, don't fear asking. If there are any typos, let me know. Writing this from a tablet. Happy late Valentine's guys!

Now time for bed.