AN: Aw, I love all my fellow Chadpay fans.

I am updating this at 11 P.M. because I don't want to do my homework. :( And I wonder why my grades are slipping.

Title: Cruel to be Kind
Rating: T
Author: MadiWillow
Summary: Ryan likes Taylor, but he can't date until Sharpay does. Chad is the only one deemed brave enough to tame the wild beast. But he didn't expect to find a human being behind her facade.
Genre: Romance/Humor
Chapter: Chapter 2

Ryan and Taylor met up on the steps of East High thirty minutes before school started, when the underclassmen were inside the building to hide from the unusually nippy wind, and the upperclassmen who actually arrived early were hanging out in their cars, in the parking lot. The two seniors sat side-by-side, not touching – just in case – and a couple of younger kids passed by them every once in a while to enter the school, not even gracing the two with a second glance.

"Did you talk to them?" asked Taylor, rubbing his arms over her light sweater.

He sighed deeply. "Yup."

"And...?"

Looking over at her, he gave her an obvious look. "You don't think that if they'd changed their minds, I would've called you right away?"

Taylor groaned. "But why? I just --"

"My crazy mother," began Ryan, irritably, "wants Sharpay and I to do everything together."

Frowning, Taylor said, "Isn't there anything you can --"

"No," he said firmly. "Taylor, you don't know my parents, okay? Nothing will change their mind. So, we have to either wait until I turn eighteen – at which point I can do whatever I want – or until Sharpay dates someone at our school." He snorted. "But that's not going to happen."

Taylor bit her lip and nodded slowly, staring straight out in front of her for a few good seconds. Surely someone at their school would be willing to date Sharpay? Zeke had liked her... there had to be someone else. There were a thousand people at East High. There's no telling if some of them harbored secret romantic feelings for Sharpay or not.

"Maybe..." she said slowly, "we could set her up with someone?"

Ryan cocked an eyebrow at her. "Typically, both people have to be interested in each other in order to be set up."

"I'm sure we could find somebody who'll go out with Sharpay," reasoned Taylor.

At this, Ryan laughed out loud. "Come on. Be realistic," he returned, still chuckling. "First of all, no guy in their right mind would ever approach Sharpay. And even if one did, Sharpay would never give them the time of day. How many times do I have to tell you that she only wants to date college guys?"

"No, you come on!" she exclaimed. "We have to get someone to date Sharpay. We just have to find the right guy. I'm sure there's some jackass, theatre loving loner guy somewhere at this school."

Ryan blinked. "Taylor. I don't know how many guys there are like that in the world. What makes you think one goes here?"

"I don't," she confessed, "but hopefully we can find a knock-off."

Ryan drummed his fingers thoughtfully on his chin. After a few moments of silence, he said raptly, "You know... you're right. We can find someone for Sharpay. And it's not like their relationship has to last. Just, begin. If they break up, my parents aren't gonna make us break up." His face split into a smile. "Let's do it."

"Okay, but, first," said Taylor quickly, "maybe we should tell the others. Seven heads are better than two, right?"

--

"... and so, we need your help."

Taylor had just finished explaining the predicament about getting Sharpay a date during lunch later that day – conveniently leaving out the fact of why she and Ryan needed her to date – and she was met with six blank stares.

"A boyfriend? For her?" clarified Chad, looking more shocked than the rest. "Mission Impossible Four?"

"No," scolded Taylor. "Definitely not impossible. Just... um..." She glanced at Ryan for help.

"Challenging," he supplied.

Gabriella nodded, frowning slightly. "Uh-huh. And, why exactly does she need a boyfriend so badly? I'm assuming this isn't her idea, is it?"

Taylor and Ryan exchanged quick glances. "Um... well... no. Not exactly."

Chad's face immediately lit up. "Oh, awesome! Are we gonna get some guy to take her out to humiliate her? I'm in."

"No," snapped Taylor. "We're just going to find a guy to take her out."

"But why?" persisted Gabriella, looking back and forth between the two of them curiously.

"Uh..." stammered Taylor, looking again to Ryan assistance. However, this time, he too was at a loss for words.

"Well, we know you're secretly dating," Troy said airily, taking a drink from his Coke bottle. "Does it have anything to do with that?"

The two teenager's mouths dropped open. "You what?!" cried Ryan.

Taylor whipped her head around to face Gabriella. "You knew? And pretended not to?"

She smiled sheepishly. "We knew you guys were trying to keep it a secret. I was humoring you."

"How'd you find out?" Taylor asked incredulously.

Six pairs of eyes rolled to the ceiling. "Come on," said Zeke. "Every day at lunch, you have to finish a Physics lab?"

"And we totally saw you two making out after the talent show over the summer," Gabriella added.

"Does... anyone else know?" asked Ryan, his eyes flickering to his sister a few tables away.

Jason shrugged. "Just us. Why?" He narrowed his eyes suspiciously.

"Well..." Ryan cleared his throat and launched into the explanation of his parent's ridiculous rules, finishing with him explaining that the only way he and Taylor could officially date was if Sharpay got a boyfriend.

Chad barked in laughter. "Good luck. I think it might be better to wait nine months for your birthday."

Taylor scowled. "Come on. We need your guys' help. Can't you think of one guy that would be willing to go out with her?"

"Nope," said Chad instantaneously.

Troy shook his head slowly, thinking. "Not really," he said. "Most of the guys I know are on the basketball team, and none of them like her."

Jason shrugged. "I could look around a bit."

Chad scoffed. "You're not gonna be able to find anyone," he pointed out.

"It wouldn't hurt to look," Zeke responded.

Yawning from apparent boredom, Chad leaned back in his seat, his arms making a triangle as his palms rested behind his head. "Whatever. Have fun."

--

Most of the seniors at East High didn't have a seventh period, allowing them to go home an hour earlier than the rest of the school. However, on this particular day, Taylor, Ryan, Troy, Gabriella, Jason, Chad, and Zeke opted to linger around the campus for a few minutes longer than usual; normally, they hung out around their cars, just talking, or they would go out for pizza, but on this special day, they scoured the school for unsuspecting candidates – or victims, as Chad put it.

They split into three groups and enthusiastically approached senior boys. Acting like salespersons, they tried their best to convince the boys to take Sharpay Evans out for a date.

They generally got similar reactions to everyone they asked.

Taylor, Ryan, and Jason asked six guys: four burst out laughing; one asked who "Sharpee Even" was; and the last walked away, pretending not to hear.

Troy and Gabriella found seven guys: three questioned, "... are you serious?" give or take a few words; two quickly, and suspiciously, stated that they were already dating someone; and two more, again, started to laugh.

Chad and Zeke only went up to three, due to Chad's strong pessimistic attitude: one said, "Not even if we were the last two people on the face of the earth," which earned himself a high-five from Chad; one stared blankly, before stalking away; and the other one just said, "No," in a very dry tone.

They reconvened back near their cars after twenty minutes with their results.

"Okay, we only asked sixteen guys," Taylor persisted. "Let's try some others."

"It's hopeless," Chad said. "We purposely picked out guys who would be willing, and daring enough, to match Sharpay's personality. No one will go out with her."

Ryan sighed. "There has to be someone!"

They lapsed into silence, all deeply thinking. Chad strummed his fingers on the hood of his car, lolling his head from side to side. "Why don't you just pay someone?" he suggested finally. "You're rich, Ryan. Just give a guy twenty bucks and he'll take out anyone."

Taylor and Ryan looked at each other, identical smiles lighting their features in unison. "That's a good idea," mused Taylor.

"Isn't that kind of mean?" probed Gabriella, frowning.

"No," said Ryan, shaking his head. "All we need is a guy to take her out on one date. Then Taylor and I can officially go out. The guy doesn't even have to take her out a second time."

"Besides," Troy said, smirking at Gabriella, "remember how much of a bitch she was to you yesterday?"

Gabriella flushed; everyone was watching her expectantly, as if waiting for her approval. At long last, she exhaled a lamented, "Okay."

"Yes!" they all said at the same time.

However, they soon found within the next sixty seconds that a dilemma was imminent: who to pay. They'd scared off the sixteen guys from earlier; at just the sight of one of the seven friends, the boys would probably hop a train to Santa Fe. And, unfortunately, they were the cream of the crop. They'd reached a dead end, coming nose-to-nose with a large brick wall and unable to figure out a way to get around it.

"We need someone who's ruthless," Taylor said thoughtfully. "Someone who isn't afraid of anything, and has just as big a personality as Sharpay."

Her eyes slowly shifted to Chad, who was chewing on his tongue and no longer paying attention. Ryan followed her gaze, and smirked triumphantly. Four more heads turned toward Chad, who, after a long moment, finally took some notice.

"What?" he asked, his eyes rolling over each of them individually. After seeing Ryan's knowing grin, he opened his mouth in horror. "No!"

"Oh, please?" begged Taylor quickly. "Please, Chad, just --"

"No," he said defiantly. "No, no, a thousand times no."

"A million times please?"

"Infinity times no," he countered. "Are you CRAZY? Why me? Me, of all people? Is there a male in this school that hates Sharpay more than I do?" He looked around desperately. "Why not Jason?" he pointed.

Ryan gave him a look. "Sharpay would make Jason cry after five minutes."

Jason scowled, but did not refute the statement.

"Zeke?" cried Chad. "Come on, he only stopped liking her because we told him to."

"No way." Zeke shook his head.

Throwing his hands up in the air, Chad exclaimed, "Okay, why is he allowed to say no, but I'm not?"

"Because you are perfect for it," said Taylor sweetly.

Chad glared at her. "I'm not doing it."

Ryan reached into his back pocket and extracted his wallet. He fished a twenty out and waved it in front of Chad's face. "Will you do it... now?" he asked temptingly.

Chad stared blankly. "Twenty bucks will not get me near her."

Sighing, Ryan took out another twenty. The five onlookers gasped, and watched the display with keen interest.

"Forty?" Chad snorted. "No, no, no. Let me map this out for you," he explained condescendingly. "Okay, so say I take her to the movies. Tickets are, what, sixteen dollars? Popcorn... that's..." he pretended to calculate the amount on his fingers, "about forty bucks. Add soda and some Twizzlers, and we're looking at around sixty bucks."

"Sixty!?" cried Ryan. "You can't be serious."

Chad clapped his hands together. "You're right! I forgot M&Ms. Add another thirty."

"Ninety dollars?" deadpanned Taylor.

Holding up a finger threateningly, he said, "You're lucky; Sharpay's more like two hundred, but I'm going easy."

"Easy?" Ryan yelped. "You're asking for ninety bucks!"

"I could bump it up to an even hundred if you like," shrugged Chad.

Ryan groaned, but took out two more twenties and a ten from his wallet, holding it out to his friend. Chad blinked at the bills and looked up. "Whoa, I only said that ninety bucks is what I'd need to take her out. I'm not actually going to do it."

"Come on, Chad," pleaded Taylor. "This is really important to us."

"Why me?" he complained again. "You have your choice of so many guys. Why must I be it?"

"Because you are the only guy that can do it," Taylor said. "You're the only one who won't take any shit from her."

Chad clapped his hands to his face and moaned loudly in frustration. He slowly dragged his hands down, stretching his skin, before sighing deeply, exhaling for a good five seconds. "I cannot believe I'm going to do this --"

"Thanks, Chad!" squealed Taylor, throwing her arms around his neck. He patted her once on the back, his face miserable, before pushing her off him.

Ryan handed out forty dollars to him, but Chad sneered. "No. Give me the ninety."

Sighing, Ryan reluctantly gave him the full amount. Chad snatched it from him and stuffed it in his pocket, looking thoroughly annoyed.

"Aww, Chad, you're such a good friend," commended Gabriella.

Suddenly, Taylor frowned and glanced at Ryan. "Wait... if you're paying Chad to go out with your sister, so you can go out with me... that's kind of like paying for our relationship." She paused. "Does that make me a prostitute?"

Chad ignored her, and said, "Okay, so, what do I gotta do? Just ask her out or something?"

"Yeah, it shouldn't be too hard," said Ryan breezily.

"You're aware that Sharpay hates me about as much as I hate her?" Chad reminded him. "I need tips. Ideas. How am I gonna get her to say yes?"

"Uh..." Ryan glanced around, and the others stared back blankly. None of them knew anything about Sharpay, or what she looked for in a man. "Well... oh, she only dates college boys."

Chad stared at Ryan for a full minute, and then gave a tiny sigh. He put his hand on Ryan's shoulder and said, "Ryan. I'm not in college. And I really don't think Sharpay will be fooled... seeing as how I'm here every day..."

"Oh!" cried Taylor. "Tell her that you're really eighteen, and that you should be in college."

"Yes!" Ryan agreed enthusiastically. "She thinks college guys are miraculously more mature than high school guys, so if you tell her that you got held back or something, she'll totally fall for it."

Gabriella laughed. "Chad, you're not gonna be able to get out of this."

Chad scowled. "Fuck," he swore under his breath. "Okay. Fine. Whatever. I'll do it tomorrow. But," he added, "if she says no, I'm not giving the money back."

"Fair enough."