Title: Tangled Up With Cupid

Genre: Romance / Humor

Rating: T for later chapters

Description: Rapunzel adored the month of February, mostly because of the holiday of love; Valentine's Day. When she discovers that two of her friends are recently single, she'll do whatever it takes to get them girlfriends. But while she's trying to hook up Hiccup Haddock and Jackson Overland, they've already begun to discover hidden feelings.

Pairings: Jack/Hiccup, Rapunzel/Flynn. Post Astrid/Hiccup

Disclaimer: I do not own How To Train Your Dragon, Rise of the Guardians, Tangled, Frozen or any other character who finds their way into this fanfic. I would only own my OC's, if any make their way into here.

Tangled Up With Cupid

Chapter One; Discovers and Planning

It seemed like a bright morning when Rapunzel woke up on February 3rd.

She enjoyed the month of February, while sure, it was still a little chilly outside, it still showed signs of the upcoming of Spring. But what she loved most about February, was that this was known as the month of love. Her relationship with Flynn was still new to her, and this would be her first Valentine's Day spent actually in a romantic relationship.

There were so many plans she wanted to set. Double dates with her friends and their girlfriends/boyfriends, making chocolates, seeing all of the other couples and not feeling upset that she was single.

Excitement surged through her like a drug, causing the teenage female to dance around her room as she dressed and got ready for school. She'd spent most of her weekend cooped up, and it was such a refreshing feeling to finally be able to leave her home and share the joy's of February. She pressed a kiss to her pet chameleon's forehead, bidding little Pascal a farewell before she left her bedroom.

"Good morning mother!" she greeted, smiling as she gracefully skipped into the kitchen, long blonde hair bouncing behind her.

The older woman looked up, giving a groan at the cheer of the girl's voice so early in the morning. She rubbed at her temples, her eyes following Rapunzel as the girl stepped around the kitchen, grabbing a bowl and pouring herself some Lucky Charms.

"Now Rapunzel, must you be so loud so early in the morning?" the woman questioned, returning her gaze to the book propped in her hands.

"Sorry," Rapunzel apologized, running a hand through her hair. "I'm just really excited."

She bit at her bottom lip, letting her eyes look over and land on her mother. For a woman in her late 30's, her appearance almost made her look more of in her late 40's. Though, Rapunzel would never admit that out loud, if she knew anything, it was that her mother's looks was more important to the woman than anything.

'Sometimes more important than me.' Rapunzel thought to herself with a frown. She shook the thought off though, she wasn't going to let it get her down. She was in a good mood and she wasn't going to let anything ruin it. Placing her bowl of cereal onto the table, she tried to pull the chair out as silently as she could as she settled herself down.

Letting her mind wander, she excitedly got started on already making plans. She could probably ask her friend Hiccup Haddock to make chocolates with her, out of all her friends she could recall him knowing how to cook. And if she knew him, she knew he'd want to make chocolate's for his girlfriend Astrid. It was kind of adorable to think of how much the boy cared towards the blonde female.

'Jack has a girlfriend right?' she asked herself, tilting her head as she chewed the food in her mouth. She vaguely recalled a female being introduced to her three weeks ago, but she couldn't remember the female's name. 'Maybe Flynn can convince him and his girlfriend to go on a double date with us.'

She nodded her head, swallowing the food in her mouth. Her mother looked up, giving a sigh and rolling her eyes. "Rapunzel, dear, don't get milk on my table." she scolded, plucking up a napkin from the center of the table and offering it out to the young female.

"Hehe, sorry mother." Rapunzel apologized again, taking the napkin and dabbing at her mouth.

The rest of breakfast was quiet, Rapunzel eating her cereal and thinking of all the plans she could make, while her mother continued to read her book in silence. When she was finished her food, Rapunzel quickly washed the silverware she had used, bid her mother a farewell and was off to school with a skip in her step and a smile on her face.

Nothing could ruin this good mood!

. . . .

"What do you mean you and Astrid broke up?!"

The exclaim was met by many looks, the auburn haired boy in front of her ducking down, his face bright red. He hadn't expected her to react like that, and now everyone was staring at them. He pressed his finger to his lips, shushing the girl before they returned to working on their class work.

Rapunzel slumped back in her seat, pursing her lips out as she looked at the boy that sat across from her. She hadn't been expecting that at all. Astrid and Hiccup were so cute together, him being geeky and frail and his girlfriend being well - popular and lead female on the girl's soccer team. They were polar opposites, and yet that's what Rapunzel felt made them so cute together.

"But it's February Hiccup." she informed him in a hushed tone.

His eyebrow raised, his eyes focused on the book on his desk. "I have a calender, I know what month it is."

"February is the month of love Hiccup! How can you guys break up in February?"

"Sorry, next time I'll make sure my next girlfriend gets the quota. Don't break up in February."

Her bottom lip pouted out, trying to let herself focus on her own book. But she just couldn't, not now with knowing that her closest male friend - aside from her boyfriend - was now single! That put a damper into her plans, but most of all, it made her want to look for someone to spend Valentine's day with her friend.

Someone to clear away the left over feelings for Astrid Hofferson.

Someone that Hiccup could make chocolates for.

Someone he could be all lovey dovey with.

"I'm going to find you a girlfriend."

"Please, don't."

"You think Rebecca is single?" Rapunzel questioned, looking over to where Rebecca 'Ruffnut' Thorston sat.

Hiccup's eyes widened at his friend's suggestion, his green eyes leaving his book to meet her own pair of innocent green's. He raked his brain for the reasoning on why in the world she'd even make that suggestion! Taking a chance, he also looked over to where Rebecca sat. She stared blankly at the book on her desk, her face clearly evident that she didn't understand at all what it was she was looking for.

"I'm going to pretend you didn't even mention that one." he said, looking back down to his book.

"Oh c'mon, she can't be that bad."

"That bad?! She's joined the boy's wrestling team, I'm pretty sure she probably has some freaky fetish for getting the shit beat out of her during sex, and do you not recall that her, along with her twin brother, have often dressed up like each other just to confuse people." Hiccup sighed, running a hand through his hair. "What if I do lose my sanity enough to date her, and she decides it'd be funny to have Tuff dress up like her and we go to some - I dunno, maybe a movie theater, and I magically get brave enough to make a move and I end up sticking my hand down her pants and feeling a c-"

"Alright! Alright, I get it.. No setting you up with Rebecca."

"How about you just don't set me up with anyone. Me and Astrid did just break up. Haven't you heard of a break before trying to find a new relationship?"

"But Hiccup, it's Feeeebruary." she whined, stretching herself across his desk and covering the pages he'd been reading with her arms.

"There's always Valentine's day next year. By then.. Maybe I'll have a girlfriend."

He shoves her arms away, trying to pinpoint where he had been reading before the female interrupted him. She gives a huff, pulling her arms back and crossing them, resting her chin on them as she watches him. She doesn't understand how Astrid could have broken up with Hiccup. They really seemed like they had it bad for each other (if you ignored the bruises left on his arms when Astrid hit him a little too hard.)

Sure, he was skinny and bad at sports. He had a body coated in spots, almost like a dalmatian. His hair was long, bangs also falling in front of his green eyes. And well.. Okay, maybe Berk was more of a place full of guys who were into football and soccer and such, Hiccup was still a good catch. He was different, and different was good.

Right?

Even if he doesn't want her to find him someone, she's going to at least look. Maybe she can at least introduce him to a nice girl, get his mind off the blonde female who broke his heart.

Rapunzel sets it as a goal, turning to look away from him as she digs through her bag for a notebook. Pulling it out, she clicks the button on her pen, before jotting down the goal in swoops of cursive lettering. She's going to find Hiccup a nice girl, someone who will mend that broken heart and make him forget the name Astrid Hofferson.

. . . .

By lunch time, Rapunzel's Valentine's plans have basically flopped on her. Turns out, Hiccup wasn't the only one who's single. She's in the middle of unpacking her lunch when her boyfriend sits himself next to her. She smiles, turning her attention away from the wrapped up box and to the boy sitting by her side.

"Hey blondie." he greets her, leaning over to peck her lips.

"Heeey~" she giggles, her nose scrunching up a little before scooting herself closer to him.

He gives a chuckle at how happy she can be. He can't understand it, because to wake up early for school, and then to drag yourself through classes full of loud chatter and a teacher talking about stuff you don't even want to listen to half the time can't be this exciting. But here she is, sitting here with a little bounce and she's got these big eyes that won't stop looking at you.

"So.." she begins, her fingers twirling a strand of blonde hair.

"So?" he questions, arching an eyebrow as he waits for her to continue whatever it is she's about to say.

"Did you ask Jack, about.. You know.. The double date?"

He frowns, and her eyes widen before her smile starts to disappear. Flynn hates seeing his girlfriend upset, but it's not like he can go and force his friend into a new relationship. "Jack and his girlfriend broke up over the weekend. So, I doubt he'd want to tag along as a third wheel." he tells her.

Her shoulders drop, her eyes moving to rest on her lunch. She doesn't feel hungry anymore, because there goes another plan out the window. First Hiccup, and now Jack. It's February, why is everyone ending their relationships?! This is the month of love, not the month of break ups and sadness. She reaches out to pick up the spork in her hand, stabbing it into her paste and twirling the noodles around it.

Should she offer the same thing she did for Hiccup to Jack? Maybe he'd be willing to date Rebecca?

She took a glance over to the female twin, who was currently shoving her brothers face into his tray of food. She winched, yeah, no that idea was dumb. Her eyes continued to scan the cafeteria, trying to find some female that might be single and willing to date either of her friends. There was that girl that Jack called Tooth, but they'd been friends for years, so surely there must have been some feelings there before, right?

But there was the tall male that walked next to Tooth, a permanent scowl on his face as the two walked over to a lunch table. There was a way he looked at the girl, and Rapunzel knew she couldn't do that, she couldn't set Jack up with his friend when it seemed someone else already had interest in her.

"Do you know if there's any girl he's interested in?" she asked her boyfriend.

Flynn gave a groan around the food in his mouth, setting his sandwich down and looking over to the small female. He watched her green eyes search the room, knowing full well that she was on the hunt for a girl to set his friend up with. Painfully swallowing, he took a minute before shrugging his shoulders.

"I don't really enjoy butting into other people's love lives."

"Really?"

"Really."

Her attention focused back on him, a blonde eyebrow raised as she stared. There was just no way, Flynn Rider actually didn't care what piece of ass his friend was interested in? Wasn't that like.. A general guy thing? To take notice of what girl their friend was interested in, maybe tease them a little or try and push them to asking the girl out?

'Maybe it's just a female thing..' she thought to herself.

He'd picked his sandwich back up, going back to his lunch and ignoring his girl's stare. She tapped her finger to her chin, maybe she should wait until Jack joins them? She could ask him when he did, maybe he'd give her a better answer than her boyfriend could.

Her attention shifted when she saw Hiccup and Astrid walk into the cafeteria. Her hopes were a little too high when she thought that maybe, just maybe they'd gotten back together. But it didn't seem like it, there was a bit of a gap between them, Hiccup didn't look like he was in a better mood then he'd been in earlier and Astrid didn't even seem like she was paying any attention to what the boy was saying.

Pouting her lip out, Rapunzel waited for something, anything really. She watched their hands that swung by their sides, but neither reached for the others hand. She watched the way that Hiccup looked at Astrid, it so clear that he still loved the girl.

"I can't do this." she groaned, stabbing at her pasta some more. Flynn raises an eyebrow, eyeing the way she's almost maiming the noodles with the poor plastic weapon. She doesn't stop until it snaps in her hand, her eyes tearing away from her friend to the now broken spork. "Shoot."

He gives a small laugh at her choice of words. Since he's know her, Rapunzel has never let a naughty word leave her lips. She's so innocent and it's adorable. Reaching over, he takes the broken item from her before she ends up hurting herself with the jagged pieces. Her eyes have returned to Hiccup, watching how he follows Astrid over to the lunch table where Rebecca and her brother are sitting.

The twins look up, Ruffnut grinning as she spots Astrid first. Thomas 'Tuffnut' Thorston is busy using his hand to wipe the food off his face, and from the distance Rapunzel can see the bits of food that cling to his long hair. Once he's sure the food is off, he slams his hand into his sisters face, the food now being smeared all over her.

Hiccup shifts from one foot to the other, she can tell he's not sure if he wants to sit down just yet, worried that the food might end up slammed into his face next. Astrid's turning her attention to him, saying something before she sits down. Hiccup looks at her, before following her lead and also sitting himself down.

Maybe they are back together?

"Ugh! I wish it was easier in knowing who was dating, and who wasn't." she mutters, crossing her arms.

"Isn't that what Facebook is for?" a voice questions her.

Looking up, she smiles when her eyes land on a familiar boy with a head of white hair. His blue eyes meet her stare, his eyebrow raised at her statement. Setting his lunch tray onto the table, he sit's himself down across from the couple.

"Who goes on Facebook anymore?" Flynn questions around the food in his mouth.

"Where else can I post multiple selfies and snow pictures? I only get stalked on Tumblr by strangers, and Twitter is just a bunch of hashtags." Jack mutters, rolling his eyes. "Hashtag love your hair, hashtag be my boyfriend, hashtag are you wearing contacts?"

"I only get one out of those three hashtags." Flynn states.

Jack ignores Flynn, his attention direction to Rapunzel as he opens the cap to his drink. He takes a sip, glancing to his lunch before looking to her as he waits to find out what she's been complaining about. He's sure she can't be talking about her and Flynn, because it's obviously clear that they're dating and let's everyone clear that they are.

"Does it seem like Astrid and Hiccup got back together?" she finds herself asking Jack, her eyes returned back to the couple in question.

"Wait, they broke up?" he questions, this being the first time he's heard it.

"Yeah, Hiccup told me earlier."

"Well, there's no surprise there," Flynn stops what he's about to say when Rapunzel narrows her eyes at him. "I'm just saying, I kind of saw it coming. She's all sporty and good looks and sure, puberty did good to the kid looks wise, but he's still horrible in the sports section."

It's true, Hiccup had showed up the beginning of the school year actually taller then his girlfriend. Not only that, but he'd gained just a tiny bit of muscle, though he was still mostly skin and bones. He'd also started complaining about having to shave, and she was sure she had caught the beginnings of stubble on his jaw before he'd narrowed his chin away from her.

But he's still bad at sports. When it comes to jogging around the football field, he's fine, a bit out of breath when he's done, but he's fine. It's when it comes to other things when he's not. Soccer, he somehow ends up tripping himself when he tries to kick the ball. Football, he's like the first target to get tackled by the bigger boys. Baseball, he's always striking out - or almost getting a ball to the face.

Overall though, there was something that attracted Astrid to him. Something that he had different then the other boy's who were fighting for her attention. How could she have easily found a flaw that would make her want to dump him?

Jack and Flynn have followed her gaze, their eyes on the back of Hiccup. Their looking at the space left between him and Astrid, enough for another person to sit between the two of them. If that's not evident enough, it's the way Astrid seems to make sure there is space between them, placing her bag in the empty space as a sort of divider.

"I'd say they're broken up for good." Flynn says.

"Seems like it." Jack agrees.

Rapunzel sighs, pushing her tray of now untouched pasta away from her. She can't find herself to eat now, not with knowing that it's really official. Hiccup and Astrid have broken up.

"What about you Jack?" she pipes up, trying to clear away her sadness.

He looks up from his lunch, slowly chewing his food as he waits for what she's going to say next. She pushes her hair away from her face, leaning forward a little so that her voice is low, as if trying to hide her words away from anyone that might pass by.

"Do you have anyone you're interested in?"

He gives a small laugh, his eyes shifting over to where Flynn has returned to eating his own lunch. Swallowing, Jack reaches over to hit Flynn's head with his bottle of water. "You told her?"

"You expected me to hide it from my girlfriend?"

"Well, I would have liked to tell her. At least not have you come tell her like it's a rumor that should be spread about."

"Oh, as if Facebook wouldn't have already shared it with everyone."

Flynn rolls his eyes, his hand rubbing at his head. Jack narrows his eyes, but doesn't make a remark about his friends words. Rapunzel watches the two banter, before looking to where her bag is set by her feet. She'll have to remember to add that to her goals.

Find Jack a girlfriend, someone who can handle pranks and likes to have fun.

The two have started to bicker with each other about Facebook, Rapunzel watches the two with a smile. While, sure she's bummed about finding out that Jack and Hiccup are single, she's going to make sure that this month gets better for the two of them. She's going to search far and wide if she has to, she's going to find the two of them a girlfriend.

Valentine's Day is going to go well, and everyone's going to be happy and in a relationship.

My, I suppose Birthday gift to you guys? The next chapters will focus more on Jack and Hiccup, with little bits here and there with Rapunzel.

I wasn't really sure where to put this. I thought at first like, Tangled crossover with HTTYD, but I'm going to be focusing on the guys more the next few chapters.. So I'm not sure. Any idea?