Author's Note: I don't own OUAT or 10 Things I Hate About You. Thoughts are in italics. I just thought writing this would be a fun idea. Reviews welcome.

In this chapter we get some Regina/Emma interaction.

Enjoy.

Chapter 2

I want to tell Robin she's my sister, but watching him fear her is just too funny, Henry thought as he watched Robin approach Emma during her Woodshop class, clutching a book to his chest for security purposes as he stepped nearer.

"Hi. How you doin? Listen, I…"

Emma stopped drilling through her block of wood to regard the boy in front of her blankly. She then grabbed the book out of his hands, took out her power tool, and drilled a hole straight through it.

She handed it back with a smile, then went back to what she was doing.

Robin glanced down at his now ruined book, rightfully scared. "Okay...later then…" then proceeded to practically run out towards his friend in the hallway. "Yeah, I don't know. She's terrifying. How are we going to get her to date Regina?"

Henry took a deep breath. "I'll ask her."

"Did you not see how that just went ?" Robin said, gesturing towards the classroom he just ran out of.

"I mean, yeah, that was embarrassing to watch," Henry admitted with a laugh. "But I'm sure she'll at least hear me out."

"Oh yeah? Why's that?"

"Emma is my sister," the younger boy finally admits.

"What?! This whole time, you could've just led with that," Robin ranted, outraged. "YOU'RE the one who wants to date little miss prissy, and I'M over here risking my life for you to ask your own sister to help you out. I swear, you underclassmen."

-TTIHAY-

"Please."

"No."

"Emma please."

"I said no."

Robin stared uncomfortably at the bickering siblings as he sat in their living room. He and Henry decided it best to wait for school to get out before they bombarded the girl with their favor, but it wasn't faring too well.

Emma and Henry were standing across from each other. Their body language speaking wonders on the situation, as the blonde girl's arms were firmly crossed and defiant, while the boy waved his arms about desperately.

"Oh come on Em-"

"Henry," she sighed. "I just don't see how this would benefit me. So no."

"But-"

"No," she said firmly, walking out of the room.

The silence that followed made Robin extremely uncomfortable. So he broke it instantly, "So now what?"

"I don't know," Henry answered, his mind working overtime trying to figure out a solution. "I mean, we could pay her? But we don't have any money."

Robin nodded, scrunching his face in thought. "Yeah, what we need is a backer."

"What's that?"

"Someone with money who's stupid."

-TTIHAY-

Killian sat with his buddies in the cafeteria as they crudely drew the female anatomy onto their food trays with magic markers. "Oh yeah, this is my best work yet."

Robin attempted to casually walk up to the group. "Hey friend, is that a fruit roll-up? Cause you don't see many-"

"Are you lost?" Killian asked, the threat clear in his voice.

"No, actually, I just came by to chat…"

"We don't chat."

Robin laughed nervously. "Well, I thought I'd run an idea by you. Just to see if you're interested."

"I'm not."

"Well, hear me out," he implored. "You want Violet, right? But she can't go out with you because her sister is insane and no one will go out with her, right?"

Standing to face the A/V nerd closely, Killian's eyebrow raised in mild interest, as he grabbed the other teen's face and began to draw on it with his marker. "Does this conversation have a purpose?"

"What I think you need to do is hire someone who will go out with her," he replied, closing his eyes as he felt the marker run across his face. "Someone who doesn't scare so easy."

Killian laughed, admiring his work as he pulled his marker away. "And who would that be?"

Emma's laughter cut into their conversation, making both boys turn to her direction where she was currently sitting with her friend Ruby. Ruby was shaking her head in disapproval as the blonde was inconspicuously making a shiv out of her school-issued spork.

Robin gestured his head in her direction suggestively.

"That chick?" the bully said incredulously. "I heard she ate a live duck once."

"Everything but the beak and feet," Robin affirmed, confidently. "Clearly she's a solid investment."

"What's in it for you?"

Hands held up in surrender. "Hey. I'm walking down the hall and say hello to you, just say hello to me."

"Yeah, I get it, you're cool by association," Killian said, sucking on his teeth a bit. "I'll think about it."

"Nice...I'll just get going then."

He quickly walked to the opposite side of the cafeteria where Henry stood, looking anxious. "Did it work?"

"He's going to think about it," Robin answered with a nod. "So now, we let him pretend he's calling the shots, while you can have your time with Violet."

Henry grinned. "Good idea," he paused, finally processing his friend's face. "Why do you have a dick drawn on your face?"

-TTIHAY-

Out in the Storybrooke playing field, the girl's soccer team is practicing, the cross country team is running laps, the marching band is going over cadences, and Emma and Ruby are subtly smoking cigarettes under the bleachers.

Taking a deep breath, Killian hypes himself up to approach the slightly intimidating pair. Deciding to just go for it, he ducks under the bleachers and stands before them as they stop to look at him.

"Hey, how ya doin?" he says, awkwardly. The two girls ignore him, taking another drag from their cigarettes. He cleared his throat and tried again, looking at Emma, "I had some great duck last night…"

Rolling her eyes, she finally answered, "Do I know you?"

Happy to get a response, he points out to the field, "See that girl?" gesturing to the brunette who was in the middle of kicking a soccer ball to her teammate.

Emma turns to look, and notices that it's the same girl Henry wanted her to go out with. "Yeah, what about her?"

"That's Regina Mills. I want you to go out with her."

Ruby bursts out laughing. "Is this guy serious?"

The blonde did not look impressed. What is with dudes and not being able to get a girl on their own? "Not interested."

Getting frustrated, Killian continues, "Look. I can't take out her sister until Regina starts dating. You see, their mom's whacked out. She has this rule-"

"That's a touching story. It really is," Emma replied, sarcastically. "Not my problem."

"Would you be willing to make it your problem if I provide generous compensation?"

Thinking back to her conversation with her younger brother, she immediately knows he has something to do with this. Guess he found a way for me to get something out of this. Alright. You win, Hen. She smirks, "You're going to pay me to take out some chick?" smirking wider when he nods. "How much?"

"Twenty bucks."

Emma turns back to take another look at Regina, who just violently body checked another girl to the ground.

Killian winced, then concedes, "Fine. Thirty."

The blonde clicks her tongue, "Well let's think about this," she began to count things off her fingers. "We go to the movies. That's uh, 15 bucks. We get popcorn. That's 53. And, she'll want Raisinettes, right? So we're looking at about 75 bucks."

"This ain't a negotiation, love," he shook his head, not liking how this conversation was going. "Take it or leave it."

She laughs. "Alright, 50 bucks and we've got a deal, guyliner."

Killian smiles widely, handing her the money.

-TTIHAY-

"Great practice, everybody!"

The soccer team is being dismissed for the day, and began to walk off the field. Emma sees this from her place under the bleachers with a smile. Ruby had long gone, as she had to meet up with her boyfriend. So the blonde decided to wait out practice and attempt her first official conversation with Regina Mills.

Throwing her cigarette aside, she approaches the snarky brunette. "Hey there girlie. How you doing?

"Sweating like a pig, actually," Regina huffs out, wiping her sweat off with her jersey. "And yourself?"

Emma smiles, attempting to flirt. "Now there's a way to get a guy's," she stops, as Regina glares and amends her statement, "-or girl's attention."

"My mission in life," the brunette says, sarcastically. Then moves her hand to her hips. "But obviously I've struck your fancy. So, you see, it worked. The world makes sense again," with that she attempts to walk away.

However, the blonde is following closely behind. "Pick you up Friday then?"

Regina laughs, a little shocked that she hasn't scared this person away, and a little annoyed. "Oh, right. Friday. Uh huh."

"Yeah, it'll be the night I take you places you've never been before," Emma said, wiggling her eyebrows suggestively.

"Like where? The 7-Eleven on Broadway? Do you even know my name screwgirl?"

I like her, she's fun. Emma smiled. "I know a lot more than you think."

"Doubtful, very doubtful," the brunette walked away briskly, leaving the blond girl standing alone.

-TTIHAY-

"We are so screwed," Henry said, it didn't look like Emma had much of a chance there. He and his friend had been scoping out the field from afar when they noticed Killian go up to his sister a little earlier.

"Hey, no hey," Robin soothed, he's put too much effort into this operation for it to fail. "I don't want to hear that defeatist attitude. I want to hear you upbeat."

Henry put on a fake smile. "We are so screwed!"

"There ya go."