A/N: Hello, there. I finally got a chance to rough outline this sucker, and it's definitely shaping up to be the longest thing I've ever written, so…every little bit of support helps! More importantly though! Coming up, there will be, I guess, spoilers for the novel The Picture of Dorian Gray by Oscar Wilde. I wanted to pick something from the AP English curriculum that would at least be semi-well-known, but I think all the mentions are comprehensible even if you're not familiar. Also, it's been a while since I've read it myself, so if Regina and Emma sound like they are full of shit, pretend they are smart (and then let me know so I can fix it!).

Belle had been startled but pleased to see Emma not 15 minutes after the library had opened, looking tired but smiling as she handed back the yearbook.

Emma had ended up falling asleep not long after processing her newest discoveries from it, her physical exhaustion from practice catching up to her as soon as her head had hit her pillow. Now she had to face the consequences of not doing her reading when she should've. She made it from the library to her locker without running into a single soul and settled down in the empty hallway to finish her work before her first period class.

Normally, she probably would've ignored it entirely, but Mr. Happ had a terrible habit of calling on people unexpectedly which was made all the worse by his cheerful disposition. Like he enjoyed seeing the terror but you couldn't call him on it. She figured some early morning discomfort would be worth being spared his focus in class. Luckily, she made short work of it, even noting the section on sediment movement that would help in her final project on Storybrooke's seawall, because as the halls filled, she became easily distracted greeting her acquaintances and locker mates, and finally, Ruby and Mary Margaret stopped by to spend the last few minutes before class together.

"Operation day two, Em!" Ruby greeted. "How are you feeling? Ready to give in yet?"

"Hey," Emma protested, sticking her work in her bag, "What happened to all your support from yesterday?"

"Eh, I reevaluated," Ruby shrugged, teasing. "Seems like it'd be more fun to watch you flail around for a little longer. And it would definitely be fun to make you Prom Queen, so…"

At the mention, her resolve solidified.

"Yeah, well, not a chance, Rubes. I also reevaluated, and my commitment is only stronger. This is gonna happen. Despite yesterday's…not-so-successfulness, I now have a foolproof plan."

"What happened yesterday?" Mary Margaret had been unusually quiet for their morning get-togethers as soon as Ruby had started with the bet, but now she couldn't keep her curiosity hidden, or the tinge of fear coloring her question.

"Oh, nothing, MM," Ruby smiled gleefully. "Emma just got massively turned down by the only person in school who would."

Mary Margaret's eyes grew wide. "You talked to Regina?"

"Yeah," Emma admitted, shooting a glare at Ruby and rubbing the back of her neck. "It may not have gone so great, but now I know, so, it's totally fine. Don't worry about it."

Emma sent what she hoped was an extra comforting look in Mary Margaret's direction, and though not entirely convinced, MM appeared to be appeased for the moment. As much as Emma desperately wanted to ask her what her apprehension was all about, she really didn't want to add anymore stress to MM's life. Planning prom was bad enough, and Emma knew she was supposed to be getting through this bet on her own anyway. She would just have to add it to the unexpected list of things she wanted to ask Regina herself. If only she could hold a more than minute long conversation with the girl.

But Emma was not about to be discouraged. It was only the second day, and Emma did in fact have a new method of approach. One she was sure would be effective once she put it into play. She walked down the hall with her friends, moving the conversation to the more neutral territory of chatting about what the day had in store—all while inwardly cursing that she would have to wait a little longer before she could really get started.

She just had to make it to 4th period.

That had been harder than expected. She had been extra glad she had decided to do the reading that morning since Mr. Happ had decided to give them a brief pop quiz just to make sure they weren't "succumbing to senioritis" yet. The planned vocab quiz in Spanish had just been boring, so that was something, but photography had been a lecture on perspectives instead of time in the darkroom and that was so not why Emma had decided to take the elective. Her tiresome morning was made all the worse by her continuous anticipation.

Never had she been so excited to get to English. It was her strongest subject, but even though she preferred the homework to other things, she didn't usually feel one way or another about the class itself. Most of the time she just doodled, ignoring discussion and typically getting away with it because of her strong written responses. But last night, as she stared at her bedroom celling, reflecting on all the new information she had gained and considering all those English tutoring mentions in the yearbook, she had realized how often Regina participated in their shared class, and impressively, if she remembered correctly.

It made sense with her smarts—Emma was pretty sure Regina was set to be this year's valedictorian—plus, she was already pegged as a brown-noser know-it-all since the teachers seemed to love her. Emma would bet she stopped by their offices in her free time just to chat. Though honestly, she couldn't remember Regina ever sucking up in class, not obnoxiously at least. Emma hadn't ever paid much attention to her, but they had been in English together before—sophomore year, she thought—and Emma didn't remember her sticking out, not in the way a suck up would. She just participated. Well. And Emma didn't really.

Well, she would on occasion, and earlier on in the year, just so the teacher would get a sense of her, but she didn't really do discussion. There were a lot of potential minefields in sharing analysis with your peers, and most did not care for when you disagreed with them, even when you were right. Plus there was always some guy that made it all about him, and it was way easier to tune that out. Besides, Emma felt it often required opening yourself up, and she wasn't much for that.

But today, she would be overlooking all of that. Phase one of her Operation (albeit plan B) finally had its forum.

She made it to her desk earlier than she ever had, not wasting a moment in the halls. She pulled out a notebook, her pen, and her copy of The Picture of Dorian Gray and tried not to sneak glances at Regina, apparently reviewing and adding to her annotations, as she waited for the bell to ring.

This was it. She allowed herself a smile.

She could do this.

Emma was not happy.

There hadn't been a good opportunity for her to catch Regina's attention all period and now they only had minutes left.

Worse, Vic Whale had spent a good chunk of time talking about how Basil was "so gay" in a way that missed its actual import and veered straight into flippant homophobia. As a result, Ms. Sanders had had to spend 20 minutes discussing how Wilde's sexuality had contributed to the novel and how it had been whitewashed in its original publication because of Victorian mores and how the very idea that someone's art would be edited because of their sexual preference was shameful as was the idea that gay people are somehow lesser. Basically, it turned into a lecture on not being a jackass, which Emma was glad for because Whale basically needed lectures like that on the hour, but seeing how she was Archie's foster daughter, and she had a mission and only 45 minutes to complete it, the whole thing just put her in a mood.

They had continued on from it, discussing the importance of Basil's infatuation with Dorian and the influence it had on him, but Emma just wasn't feeling it. She needed to make sure she said something resonant—Regina might notice if she participated for once, maybe, but it wouldn't help any if she thought Emma was an idiot.

"What about Lord Henry?" Ms. Sanders' question cut through her thoughts. "We've spent most of our time today on Basil's relationship to Dorian, but Lord Henry's relationship with him is going to become even more important very soon. How do you think Dorian and Lord Henry will end up affecting each other? Will it be anything like Dorian and Basil?"

The room remained quiet for a few moments, the way it tended to whenever Ms. Sanders had to make a direct appeal for discussion. There was something about breaking that silence that most avoided, but not Regina. Her hand was up relatively quickly after the question had been posed, but she had offered a good deal of thoughtful commentary earlier on before the Whale debacle, so Ms. Sanders was slower to take the lifeline than she would've been normally.

Emma had her chance.

She propped an elbow up on her desk, raising her hand high enough to catch Ms. Sanders' attention but casually enough to remain seemingly indifferent.

In the world of fishing for a teacher's response, this was the genuine worm lure.

"Emma?" Ms. Sanders responded instantly, cheerfully surprised.

Sitting up a little straighter, preparing to speak, Emma just barely caught the glimpse of disappointment Regina let through as she dropped her hand. Though as much as she tried for disinterest for whatever Emma could have to say, her mask was faltering. Emma could tell she was invested in what came next. Whether that was because Regina recognized she never participated or because of their interaction the day before, Emma couldn't tell. Whatever the reason, it was fine by her.

"I think that their relationships will be kind of similar, but the results will probably be really different."

Emma tried to hide the cringe she felt rolling through her muscles when she caught Regina's not-insignificant eye roll. Sometimes she wished she were a little more eloquent. Luckily, Ms. Sanders still looked invested and seemed to will her to continue.

"What I mean is, they both—Basil and Lord Henry—they both look at Dorian as artists. But Basil's art is about preserving Dorian, like catching every last piece of him in his portrait, not just like a photograph, but his actual perfection. Lord Henry also thinks of Dorian as a possible work of art, but to him, Dorian's unfinished. He sees potential to shape him, like a sculptor.

"So, even though they both have artistic sensibilities about Dorian, Lord Henry needs him to meet his vision to be successful, which means that Dorian is going to have to change to do it, and Henry won't have to change at all. It's his vision, Dorian's just the material. And that's why even though he talks a good game with this new hedonism stuff, he's an artist, he doesn't have to live out his work—it's all talk."

So it wasn't perfect. But Regina was looking through her highlighted passages, scribbling something in one of the margins with a slightly furrowed brow, and Emma could swear it was because of what she had said.

Between that and Ms. Sanders' massive, grateful, impressed smile, part one of phase one of her Operation was a major success.

"Very interesting observation, Emma," Ms. Sanders praised. "I wonder, do you think that his being an artist will keep Basil from changing in response to Dorian? Or will the changes in his subject mean that he will have to make accommodations to retain his love for him?"

In the rush of the moment, Emma had forgotten that participation sometimes came with follow up questions. She spotted brown eyes across the room not bothering to hide their interest.

She could do this.

"Yeah, he'll probably a change little," Emma acknowledged, allowing herself room to think. "But Basil's motivation is always going to be getting Dorian to return to what he was, to his innocent perfection, so he will probably stay mostly what he is, because that's how he can define what he hopes for Dorian. Any accommodating would mean Dorian wouldn't be able to entirely regain what he's lost. Basil'll just be freaked by Dorian's new behavior."

Emma smiled, slouching back on her desk like she hadn't been putting all her hope into this one response.

"Fine point." Ms. Sanders smiled in return, particularly pleased with the idea of Basil Hallward being "freaked". She glanced at the clock with the sixth sense some teachers seemed to have about just how long 45 minutes was. "Let's pick this up tomorrow! You'll be seeing even more of Lord Henry's influence in tonight's chapters."

The bell rang as soon as she finished speaking, and everyone moved to gather their things and head out the door. This was where step two of Emma's plan came into play as she made sure to pass Regina on the way out.

"Hey," Emma spoke softly, slowing as she went by, waiting for Regina's eyes to meet hers to confirm that she was listening. "You were totally right about that sins quote earlier. Lord Henry is full of shit. Thanks for calling it out. You were impressive."

Had Regina been reaching for anything as she packed in that moment, she absolutely would have been thrown off balance. What on Earth was going on that Emma Swan would talk to her—again?

She mustered all her reserves to throw her masks in place and come up with a scathing response, since clearly the compliment was meant to throw her, and how could Emma possibly be good at analysis anyway, when she realized—the blonde had left, her curls following her out the door with a bounce.

No cornering. No pushing for plans. No repeat of the library.

Regina stood, utterly confused, not even fully invested in dispelling Ms. Sanders' worried glances.

The bell rang again.

Regina was shocked to find the room empty, her book still sitting on the desk, next to her open bag.

She shook her head, stuffing the book in and pulling the zippers shut, heading to the practice rooms.

That wouldn't be happening again. It couldn't.

Whatever Swan was up to, Regina was determined to ignore it.

Emma plopped down at the lunch table where most of her friends already sat, back to their usual, still riding her high from the period before.

"How'd it go?" Ruby instantly asked, apparently having filled in the rest of the gang on Emma's new plan in the few minutes before she showed.

Emma met all of her friends' looks of anticipation before answering with a grin.

"We're back in action, Rubes."

Ruby, Emma, and Tink slowly walked back to town, the first two hindered by their sore muscles and the third just keeping them company.

They had spent most of their walk together discussing other, non-prom related things. Or at least they had until Tink had begun to question whether any of them would be asked to prom by someone they actually cared for, nervously twittering until Ruby called her out on her desire that Killian get it together enough to ask her properly.

"I—I wasn't talking about that. I wasn't thinking about that at all! Ruby Lucas!" Tink sputtered.

"What?" Ruby cocked any eyebrow, appreciating Emma's inability to hold back her laughter. "It's no secret you've got the hots for Hook, Tinkerbell." Tink scowled even deeper, not appreciating the comparison at all. "Besides, you two will clearly be going together anyway, since he's not about to ask me or Ems."

Emma scoffed at that even louder, but Tink snapped back.

"Why wouldn't he? We're all friends, and the only one who's currently dating someone is Mary Margaret."

"Tink, Ruby and I do not want him, and anyone with eyes can see he wants you. You just have to get him to stop being stupid and do something about it. He may be an idiot, but he's your idiot."

Ruby slung an arm over Tink's shoulders, nodding vigorously with Emma's analysis. Tink flashed from confusion to wonder to eagerness and back to a scowl as she pondered the truth behind Emma's proclamations, but she shook it all off, content to back off the subject for now.

"Then who will you two be going with?" She questioned casually.

Emma and Ruby looked at each other but they were spared from answering by Tink's rapidly shifting train of thought. "Oh! Regina. Are you going to go with Regina? I mean that's not part of the plan, but if you're going to be friends and you don't have a date…Oh, wait, Emma!" Tink exclaimed, pausing. "I didn't get the chance to ask Kathryn—"

"No worries!" Emma cut her off. She had forgotten to remind her during the day, and she couldn't help but be a little glad that Tink hadn't followed through if her subtlety in bringing up Killian was any indication. "Hold back on that for a bit. Don't want to scare her off," she continued with a smile.

Tink took her reassurances instantly and continued with their walk to town, wondering instead if that August guy would come back to town just to ask Emma, but Emma caught Ruby shaking her head in laughter at her out of the corner of her eye.

At least someone was having a good time because of their bet.

As the days progressed, Emma fine-tuned her approach. It was a delicate process.

She hadn't wanted to press her luck with too much in one go, especially when she had so drastically fumbled their first encounter, so she had refrained from doing anything after English on Tuesday. Besides, she needed the time to learn Regina's schedule.

It wasn't perfect, but thanks to some help from Ruby and Tink she had a general sense of where she would be when. She had asked her friends to keep an eye out for Regina during passing periods, and between the three of them, she had managed to note at least what parts of the building Regina would be in without being too terribly creepy.

Wednesday, she commented again in English, much to Ms. Sanders' delight, and she praised Regina's work after class, this time adding a question about the novel that she would have to respond to.

Regina had answered with something terribly brief and walked away, this time leaving Emma standing alone, confused.

Emma hadn't expected her to crack right away, hardly, but she had expected a little more give as opposed to a renewed cold front. But it was only day two of her new attempt, and she had more planned.

She just had to find her during their free period but make it look like happenstance.

Then tomorrow, she just had to stay in geoscience long enough to see Regina turn the corner of the science hall. She had definitely seen her there before.

Piece of cake.

Regina powered through the halls, deep in thought.

Emma had talked again in class. She had approached her again afterwards, for a combined total of three times.

Three whole times.

Regina was no closer to discovering Emma's end game, and it was throwing her off. She had had a hard enough time clearing her mind during her ride the day before, and she could only imagine today. She had half a mind not to go at all lest she lose track of time all together and wind up on the end of one of Mother's less pleasant methods of discipline.

But she wouldn't let Emma ruin the little joys she had left—not that she was trying to, Emma was hardly insidious enough to be doing it on purpose. The blonde was smarter than she looked, apparently, but she didn't have the mind for this obscure sort of bullying.

That was ridiculous—she couldn't even know Regina well enough to know that this was bothering her. By all appearances, Emma Swan was just being nice.

But why?

The question nagged at her, more than any outward display of hate.

Unfortunately lunch just left her time to ruminate. She thought about working even further ahead or better, reading a Molière that she thought she might actually be able to get through, but as she turned the page, slowly eating the bag lunch she had been lucky enough to think to bring, she realized not a single word had made its way into her brain. She had just been staring. Mindlessly.

Sighing, she put everything away and headed straight to the piano in the practice room she spent her lunches in. She'd just have to play until she could only hear the music in her head.

The bell rang her out of it, and she was grateful for the distraction of her next class but upset that Wednesdays weren't a lab day. She would have to deal with a whole other free period.

Chemistry passed quickly, and she left it feeling better—she liked the logic of it all, and their teacher had assigned what she could already tell would be a challenging problem set, requiring her full attention. She could easily spend her free period doing that. Instead of wasting her thoughts on that pesky blonde.

She put her head down and made her way through the passing period crowds on the way to the library, when someone glanced off her.

It happened on occasion, sometimes on purpose, but when she looked up, she found something much more threatening than some brutish jock.

Emma Swan and her lopsided smile.

"I'm so sorry, Regina—are you okay?"

Emma couldn't believe her luck actually bumping into Regina in the hall, especially when she caught the bewildered look on her face. Emma kept a hand on her arm, surprised at the softness of sweater Regina was wearing and that she was being allowed in the girl's personal space. It was just air after all, but everything about Regina seemed so impermeable.

Soon enough though, Regina seemed to notice the hand lingering and shook it off, taking a good step back and crossing her arms around her.

"I'm perfectly fine. Watch where you're going."

Regina may have been spitting the words, but Emma couldn't help but think this time, she had shaken her walls. Who would've thought a simple touch and a simpler question would have that kind of power?

"Of course. I'm sorry again. See you tomorrow!"

Emma sauntered off, not pressing, content in waiting for their next encounter, and not bothering to look behind her.

Had she done so, she would've seen Regina practically frozen to the spot, before hurriedly turning and heading in the opposite direction.

Thursday.

Emma caught Regina in the hall in the morning, just as she had planned, this time casually saying hi as she passed, and then rushing to get to Spanish on time.

She participated in English. Again.

She came up to Regina afterwards, elaborating on a point she had made. Again.

Emma was starting to get frustrated though. Her little moments didn't seem to throw Regina off anymore. Not that she was sure that they weren't but Regina was definitely getting better at hiding her true reactions. She was tolerating their meetings, but Emma swore she wouldn't be any more open to an invitation than she had been that first day in the library, which was not okay. She had a limited amount of time here, and she had found something in nearby Rockland this Saturday that she had good faith Regina would be interested in attending, which for a town of about 7,000 was incredibly lucky.

She made her way through the halls to the cafeteria, wondering if there was something she could do to up her game as she joined the line for hot lunch.

"Hey, grab me a cookie?" David had snuck up behind her in line, full tray in hand, and nudged her with his shoulder.

Emma smirked at the athlete's seemingly endless amount of terrible food, but grabbed him that cookie all the same, M&M, since it was the one thing Mary Margaret was probably going to steal from her boyfriend, considering her wicked sweet tooth.

David smiled graciously as she placed it on his tray, confirming that he was getting it with his girlfriend in mind.

They both paid and walked to their table where Mary Margaret was already waiting with Ruby, chatting amiably.

David set his tray down and climbed onto the bench with a kiss to his girlfriend's cheek, immediately rearranging his lunch to leave the cookie on the closest edge to her.

Emma and Ruby didn't even react to the ridiculous sweetness anymore. Mary Margaret and David had been officially together for years now, and while Emma had never believed it possible, watching the two of them made her think that those couples who still loved each other after 80 years could exist after all.

"Bulking up for the big game, huh?" Ruby snickered at David as she took a huge bite out of her own sandwich.

"What can I say, I'm a growing boy," David smiled in return, biting off a hunk of chicken tender.

"Do you want to come watch with me tonight, Ruby? It's a home game. And Billy's starting today, right David?"

David nodded, amused by MM's perpetual instinct to find what they had for others. Ruby looked a little less comfortable than usual, and Emma picked up on it right away.

"I don't know, MM," Ruby hedged, "Maybe I'll stop by after practice."

Mary Margaret was swayed by that and smiled at her friend in easy acceptance, turning to her food. Emma shot a look in Ruby's direction, attempting to glean whether this thing with Belle was important enough to her that the normally coquettish girl wouldn't even want to flirt with someone else, but instead, she caught a flash of dark brown, leaving the lunch line.

She tracked it, spotting Regina weaving out from the crowds with a rather sad looking salad in hand.

The rest of the table had noticed her stare, but had thought it to be for Tink, heading towards them with Killian on her heels, but Emma hadn't reacted, even as her friends drew nearer. Her head turned, watching the girl go past, but as Regina turned, scanning her environment, she caught Emma's waiting eye.

Emma waved. It was across the cafeteria, but she knew Regina had seen. And perhaps more importantly, a few of their peers had, too, besides the giddy ones at her own table. Maybe if she couldn't actually get Regina to be her friend she could make it seem like they were? But that hope was dashed when Regina ignored her entirely and walked back out the doors, leaving Emma reddening with her hand in the air. But she'd recover. And small steps were important.

Right now, it would just be about shutting up her friends as they teased her about her failure.

Regina had a difficult time steadying her heartbeat.

Emma had waved. Waved at her, in front of essentially their entire class. Regina had faltered slightly, but found it within her to ignore it, walking back out the way she had come as decisively as she could.

She had felt the tug though.

The desire to walk over to that table and say hi in return. The wish that she could sit down and have lunch with a group of her peers, her friends, instead of hiding away in her favorite practice room, eating quickly to spend the rest of the period on the piano. Was that what it was like to be a normal teen? To be greeted kindly in the rabble?

She hated Emma Swan for making her doubt her place in the system, the place she had grown comfortable in, the one she knew she couldn't rise above.

And she loved her for it.

Could the blonde possibly be sincere in her attentions? The question of why remained. There wasn't any reason for Emma to be interested in her or her friendship. There was nothing to gain. She seemed perfectly capable of passing her classes if her work in English was any indication; she had no grand designs on power that Regina could tell; and she had been in town long enough to know that even if the Mills family was wealthy, they did not share that wealth with anyone. She was popular and Regina was not. Emma Swan shouldn't be talking to her. There wasn't any reasonable explanation.

Did there have to be a reason?

Regina shook her head of the thought, moving faster towards the music wing, craving the surety of her keys.

She'd be impressed if she managed to eat any lunch at all.