I'm so excited to write this :) I am a teacher actually so the situations and such in this story come from what I think could be realistic scenarios...and for some reason, I just think these two would be so funny to watch in this sort of setting. I hope you enjoy and as always, comments and thoughts are greatly appreciated!

*All rights and characters belong to the creators of OUAT.

Thank god she had made it back. A cool early spring breeze hit Emma's cheeks as she stepped out of the driver's side of her car. She pulled the sleeves of her knit cream sweater down over her hands as she wandered to the front of the diner to wait for Ruby.

Normally, Emma would not permit Ruby and her promiscuity to housesit for her under any circumstances, but she'd been coaxed - more like forced - into this three day teaching conference in New York at the last minute. Her plants weren't going to die because she had to spend half the week listening to someone drone on about something. Teacher training seminars were quite tedious and the messages they advertised seemed to all run together after a while.

She smirked silently as she remembered how she'd been coerced into this whole thing in the first place. Stupid faculty meeting and stupid, stupid adult boys, she thought.

"Okay, everyone, I received a call this morning that they've opened a few additional slots to that new age teaching methods conference in New York next week," Principal Hopper announced. "Now back when the registration first opened, Anna had expressed an interest in going - quite the enthusiastic interest actually. However, she's been called back to her hometown for a week or so to deal with a family matter regarding her sister. That being said, I need to fill her spot - and fast."

Emma cringed in her chair. Teacher trainings were right up near the top on her list of dislikes. She heard a suspicious cough from a couple rows back and slowly turned to peer at the source. Stupid freaking Killian Jones. He winked at her and gave her his best overly charming smile. This was a reason - well one of the many reasons why she refused to sit by him during meetings like this. That flashy, flirty grin was just too much to deal with.

He and Robin were the absolute worst. Although they played coy and careless, Emma had seen the passion both men demonstrated when teaching. They were each a wealth of knowledge - particularly Killian and his confident, talented carpentry hands. She had often wondered what caused two skilled, charismatic men to act like such arrogant, noncommittal idiots at school staff meetings.

Every third Monday of the month, those two fools would show up to the required staff meeting in their best suits - clean cut pressed linen and the works. It was quite the obvious change from the two laid back, well-liked transplant teachers who on any other given day would be rocking plaid flannel shirts and suede sneakers. Well, perhaps it wasn't as obvious to everyone else as the men's - more like boys' - professional mockery seemed to charm even the crankiest colleagues. They were even able to elude their kindhearted principal who always complimented them on their nice, clearly newly acquired clothes. They both lived it up as they enchanted and took advantage of the naivety of everyone in the room - except Emma. Yet although she saw right through their facade, it didn't mean she couldn't also admire the scenery - wait, no - no, she was totally onto their dumb little game.

"Now I know it's a big commitment to go to a seminar alone for three days," Principal Hopper tried gently but in a less than convincing manner. "But it seems like such a great opportunity to grow and really incorporate some diversity into our school structure."

Emma laughed inwardly, a clever smile on her lips. She could practically feel the magnetic eyes of many faculty members moving toward those two handsome, British bastards. Any time there was a promise of "diversity changing lives", Killian and Robin found themselves right in the line of sight. Hey, that's what you get when you hop across the pond to teach in a nearly unknown, sheltered small town.

"I think Emma should go."

Emma froze in shock. Oh hell no he did NOT just say that. She felt his smug, sarcastic eyes burning a hole in her head as she turned to address his backstabbing and totally unnecessary, unexpected idea. She tried to mentally prepare a rebuttal as she locked her gaze on his unwavering blue eyes.

"Wait, hold on, why would you think-"

"Well, Emma is such a cornerstone of the faculty here," Killian embellished in an endearing tone, addressing everyone. "She would get so much out of an opportunity like this. She's a person we've all looked up to when it comes to education. She would be the best equipped to go and well, we all know test scores don't lie. The woman clearly knows what she's doing."

Test scores my ass, she thought. What a son of a bitch. She glared at him viciously as he simply smiled sweetly back.

"You know," Robin chimed in just for good measure. "Sounds exactly like the kind of teacher that I would love to represent our school in New York. Plus it's the Big Apple - I mean it's more like a paid vacation with all the sights and whatnot."

She was so irritated that both men were so stone cold talented at keeping a straight face. She knew this was all Killian's doing, but it wasn't like Robin minded being manipulated into such a situation at Emma's expense.

"I think that you two gentlemen make some fine points," Principal Hopper agreed excitedly. "I know you'll enjoy having such a unrivaled learning experience, Emma. You're okay to go, right?"

"Well, uh - okay, I guess," Emma stuttered as she realized refusing would be futile. "I guess I can go."

Principal Hopper nodded in appreciation and then continued onto the next item on the agenda, squinting as he viewed the bulleted topics. Emma stealthily retrieved her phone from her bag and located Killian's number. She glanced up quickly to see everyone disinterestedly engaged in some technology budget report as she opened her messaging screen.

Emma: You know that the deepest circles of hell are reserved for betrayers and mutineers right, Jones?

Killian: Not that I don't love your wit, but are you accusing me of piracy, love?

She rolled her eyes at his little sentiment. He only said it when he was terrorizing her so flirtatiously. It made her fume and she could see how much he loved making her squirm.

Emma: Well you may as well be one with the way you sold me out back there you damn scoundrel.

Killian: What can I say other than I'm thrilled for you to 'have such an unrivaled learning experience' ;)

Emma: I can think of a few things I want to say to you and your accomplice over there. Tell Robin that his tie looks ridiculous. He looks like he's late for prep school graduation.

Killian: Easy, love. He really helped lobby in favor of you going to NY just now out of the true kindness of his heart. Perhaps gratitude is in order?

Emma: I hate you both...and your little bromance that seems focused on tormenting me. Now stop texting during meetings. It's doing nothing for your faux professionalism.

Killian: Fine line between teasing and tormenting, Swan...and although I can't speak for Mr. Loxsley here, I am always a very well-mannered gentleman.

Emma: Shut up...

Killian: Fine. But one more thing?

Emma: Ugh, what?!

Killian: Bring me back a t-shirt ;)

She shook her head as she gave him a filthy look, shoving her phone forcefully back into the front pocket of her purse. She didn't miss the way those two jerks gave each other a sneaky, underhanded low five. Emma spent the rest of the meeting thinking of where she could buy the most embarrassing souvenir possible for that low life Mr. Jones.

Killian: For the record, I meant what I said about you being a great teacher :)

Emma read the last message on her phone with a far too ambitious grin. She quickly composed herself, but when she turned to find him, he was gone.

Ruby finally showed, but only twenty minutes late which was actually better than usual. She carried a small stack of mail - Emma wouldn't be returning home until later that night so she'd asked her to bring it. Perhaps she had also made that request to see if Ruby truly had managed to keep track of things while she was away.

"Here you go, sheriff," Ruby said in a patronizing tone, taunting her authoritative nature with a snide nickname. "One ridiculous stack of mail for Emma Swan. Do you realize how many credit cards you could have? It seriously seems like people want to give you free money with all the pre-approved envelopes you get."

"Which are, surprisingly enough, still sealed. Point for you, Ruby."

"Be careful, Emma," Ruby retorted, pointing a teasing finger at her. "If this house sitting thing takes off, you might not be able to book me so late in advance without a healthy convenience fee."

"Ha! Well that's okay because I could just pay you with all that 'free money' you claim I could get," Emma laughed freely. "All of our problems solved."

"Exactly! I knew you'd start to see things my way eventually. So breakfast?"

"Nah," Emma replied as she thumbed through her mail. "I've got to get to school and make sure nobody died or set fire to the classroom while I was away."

Her phone chimed in her back pocket and she set to retrieve it as her fingers stumbled across a thick envelope near the bottom of the stack. She felt its odd importance and she set it on top of the others, but not reading it. Her phone had demanded attention first so she figured it could wait a minute. She saw the name flash on her screen that alerted her of a new text and she proceeded into a dramatic eye roll. She should have just read the contents of the envelope instead.

Killian: I shall assume you have made it home and that you are anxious to make amends with me - bring coffee as a peace offering. See you soon, Swan.

"Come on, Ruby," Emma stood and gestured toward the door of the diner. "I think I have time for a quick cup of coffee."

Emma was having coffee with Ruby because she wanted to and she needed to get the details on what had happened in town during her absence. It had absolutely nothing to do with getting Killian a hot, freshly brewed to-go cup before heading to school. Hell, she didn't owe him anything. Actually, if anything, it was him who owed her.

She slid into the booth closest to the front doors, still clutching the envelope. Ruby set off to the counter to get them some hot mugs - her grandma still owned the place so she made her way behind the counter to fix up their drinks as Emma mused over the mystery mail.

Yep, here it was. She'd been afraid of this. Dammit.

In big bold letters, the return address told her rather enthusiastically who the letter's happy sender was: The Future Mrs. David Nolan.

Honestly, Emma loved her cousin, David. They'd been extraordinarily close growing up in Boston - Emma's parents traveled endlessly for work and she'd spent more nights on an air mattress at his house than in her own bed. David had always looked out for Emma - giving her rides to school when he didn't have to, talking her into getting her teaching degree, and even punching her ex, Neal, right in the face before he even knew the circumstances of their breakup. In all fairness, he did deserve it.

"What ya got there?"

Emma had been so wrapped up in wrapping her mind around this piece of mail that she was startled when Ruby plucked it right out of her hands.

"Oh is this from Dave's new girl?!"

"Well it looks like she's not just his 'girl'." Emma said, a little annoyed as she snatched the envelope back. "Fiancé might be more appropriate."

It shouldn't have been a surprise and as Emma thought about it, she realized it really wasn't. He had gone on and on about Mary Margaret for months before Emma actually met her. David didn't usually introduce his girlfriends to family so when he had arranged for them all to have dinner, Emma knew it was big. He'd tried to call a few times while she had been off in New York attending the conference from hell - at least that was one of the headlines of the guilt trip speech she was going to give Killian. She wondered if the engagement had been the reason behind the vague voicemails David had left her.

Mary Margaret was a great match for Dave. She was a sweet, wholesome girl and as much as her personality should have clashed with Emma's - it didn't. They talked quite freely and Mary Margaret took such a genuine interest in anything and everything Emma had to say. She was glad they'd got to meet since she figured the two were headed for bliss, but after a few hours discussing domestics and "the future", Emma found herself quite out of place and totally ready to go home. They were so taken with one another that Emma had taken the term "third wheel" to a whole new level of lame.

Emma didn't have an issue with her cousin or his betrothed. She had an issue with the invitation to the engagement party that Ruby had somehow stolen again and was currently skimming.

"So they're doing it in Boston after all," Ruby mused as her eyes moved across the fancy lettering. "Oh my hell, Emma. Look."

Ruby flashed the R.S.V.P. card at Emma. They'd given her a plus one. God dammit, David. Emma could practically feel his smirk burned into the pretentious paper invitation.

Her mind drifted to the intense string of events that would surely occur over the next few months - this party, at least one wedding shower for sure, and the big event itself. God, the actual wedding - and they'd given her a plus one.

"So what's your plan?"

Emma pursed her lips at her friend's question. She definitely couldn't call them on it - that would only magnify the fact that she was alone and create a strong implication that she wasn't okay with that. She couldn't go alone either. She'd spend the entire time being grilled about where her boyfriend was and when they were getting hitched. There were reasons she avoided going to family events in Boston and that was one of the main ones. She couldn't just skip out altogether - she could never do that to David. She had to figure something out and she knew she shouldn't call her cousin back until she'd formulated an agenda. Emma dropped her forehead against the cool countertop, frustrated beyond words that none of her options were even mildly appealing.

"You can always come with us," Ruby offered as Emma raised an eyebrow at her. "With me and Victor."

"You guys got invited to this thing too? Wait, you knew about this?!"

"Well you know how guys are," Ruby explained with a flourish of her hand. "Dave said something to Victor just before the proposal. He'd mentioned a few possible dates. Probably just wanted to see if it would clash with Victor's residency."

Ruby was trying her best to make light of the whole thing. Emma began to laugh sarcastically as she ran a hand down her face in sheer dread. She was doing everything possible with one cup of caffeine to think of a valid excuse to not tag along as an accessory to Ruby when her phone chimed again.

Killian: Oh come on Swan! If you were a barista, you'd sure be a poor one and I would never tip you. My first class in in 40 minutes and operating power tools is frowned upon when the operator is groggy from a late evening of scotch and regrets with his thieving best friend.

Emma groaned dramatically at how infuriatingly exasperating and dashing he was. He commits her to a training in New York alone for three days to save his own skin and then he has the nerve to tell her to brighten his morning with coffee. Seriously, who the hell did he think he-

Oh my god.

Emma's eyes went wide with an idea - a crazy one perhaps, but it was something at least. She didn't have time to think the details through at that exact moment, but she could hash that out on her drive to school. She'd admit she was in crisis mode and this spark of inspiration on how to make the endless wedding shenanigans more bearable was probably way too impulsive. Either way, she was about to find out.

"Hey Rubes, I gotta go," she said as her friend refilled a fresh to-go cup for her. "Thanks for everything and I will catch up with you - later this week?"

Ruby simply nodded. She was clearly aware that wheels were turning in Emma's head and seemed to be rather interested in seeing if a train wreck was about to play out. Emma hurried across the road to her car, pulling her phone out as she opened the door.

Emma: Hey idiot - yes I'm back and yes I will bring you some caffeine. Not quite ready to totally make amends but I've got a proposition for you that could put you back in my good graces. See you in ten. Be there or drink cold coffee.

Emma clicked the lock screen button on her phone as she tossed it on the passenger seat. A sly smile crossed her lips as she buckled up.

Oh, yes. This was going to be way too fun.