Disclaimer: I do not own High School Musical, the songs included in this story or the characters.

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Here's the deal, Troy never met Gabriella during his vacation but he did do the whole karaoke thing and discovered that he can sing. And that little crush that Sharpay had on Troy well that's over with. She despises him. I'm not sure if I'm going to be including Gabriella in future chapters, but I might.

Summary: "If you can make the Ice Queen's icy heart melt then I will run around in a dress during practice. Deal?" Troy Bolton has to find a way to melt Sharpay Evans cold heart but what if he finds himself falling for her?

Chapter 1
The Bet

"Troy it's time for school. You don't want to be late for your first day back after Christmas Vacation do you?" Troy Bolton grunted and turned to look at the clock beside him.

"Mom it's seven o'clock in the morning." Troy complained as he turned back around and closed his eyes.

"I thought we could get a few minutes of basketball practice before school son. Gotta get you in tip top shape for this season." Troy's dad answered outside of the door.

Troy groaned in reply but still got up. He took a quick shower and changed into his clothes and then went downstairs for breakfast where his dad was already holding a basketball. Troy's mom looked at the both of them disapprovingly, "Is basketball all you two ever think about?"

The two glanced at each other and answered, "Pretty much."

The truth was though Troy had another passion and it was singing. Not like he would ever tell his dad that. He never really thought much about singing until one day he got dragged in front of a karaoke and was forced to sing, he thanked god his dad wasn't around to see that.

After the two had eaten breakfast they quickly went outside for some basketball. A few minutes after their game Troy's dad looked at his son proudly, "Keep this up son and you'll have a full basketball scholarship." He ruffled his son's hair and went inside to get ready to go to school seeing that he was the school's phys ed teacher and the school's basketball coach. After Mr. Bolton had changed the two said goodbye to Troy's mom, Sarah, and left for school. Troy's dad dropped Troy at the front of the school where the whole basketball team was waiting for him, while he went to park his car in the staff parking lot.

"Troy!" The entire greeted him enthusiastically.

"Hey guys. Happy New Year. " Troy grinned and walked with them.

"How was your vacation?" Chad Danforth, Troy's best friend and fellow basketball teammate asked.

"Nothing new. Basketball practices that kind of stuff. How about you guys?" Troy said leaving out his karaoke expeditions during the summer.

"Same here. With you leading us to the championships it will definitely be a happy new year." Chad grinned happily.

"What team?" Chad asked loudly.

"Wildcats." Troy and the entire basketball team yelled out.

"What team?"

"Wildcats."

"What team?" Chad yelled louder.

"WILDCATS!" The team cheered as they entered the school.

Suddenly Sharpay Evans and her twin brother Ryan entered the school; their heads raised up high, and walked through the halls. The team stared at Sharpay and shuttered.

"The Ice Princess is back." Chad pointed out, "Is it just me or does she get nastier every time she comes back?"

"No it's not just you. I see it too. She probably didn't get what she wanted for Christmas." Their fellow teammate Jason Cross answered.

"C'mon let's go Miss Darbus will have a fit if she finds out were late." Chad and Troy soon went to their first class with Ryan and Sharpay.

The two entered the class and quickly sat down on their seats. Sharpay and Ryan then entered carrying a gift obviously for the teacher. The two walked towards the teacher and handed it to her.

"Here Miss Darbus," Sharpay said sweetly, "We got you something for Christmas."

"Why thank you Sharpay." Ms. Darbus replied as she eagerly took her present and opened it. Inside was a box of chocolate truffles as soon as Ms.Darbus saw the chocolates her eyes immediately lit up.

Sharpay smiled at the delighted look on her teachers face, "Ryan and I went to New York for Christmas and we thought we'd give you something you'd definitely love. It's imported you know." She pointed out.

"How very generous of you two." Ms. Darbus thanked the twins once again before instructing them to their seats. As the two were walking to their seats someone Chad was talking to Troy out loud, "Can you believe that two? They're such suck ups." As soon as he heard this Troy laughed agreeing to what Chad said.

Unfortunately Ms.Darbus heard the entire conversation, "You two boys can learn from Ryan and Sharpay's behavior. Detention for both of you. I'll be needing some help to build some new sets for the Drama Club's new production."

"But Ms. Darbus we have basketball practice." Jason Cross, Chad and Troy's fellow basketball teammate, protested.

"That's fifteen minutes for you too Mr.Cross. Anybody else?" Ms.Darbus asked the class impatiently. The class was immediately quiet.

"Good. Holidays are over people. It's time to get back to work. Put you're thinking caps back on."

"It might be hard for Chad to find his." Taylor Mckessie, resident smart girl and president of the Decathlon team, said.

After the class was over Jason, Troy, and Chad headed over to the auditorium following Ms. Darbus. The three entered the auditorium and were each handed a paint brush.

"You will be painting the new sets for the new Drama production. Now get to work, the sooner you do it the sooner it will be finished." Ms.Darbus told them before she left.

The three immediately got to work. Chad lazily painted his set then glanced at the stage where he caught sight of the twins practicing, "It's all Ryan and Sharpay's fault. If it wasn't for their stupid gift we wouldn't have gotten here. Coach is gonna kill us once he realizes that were not at practice."

"At least he's only you're coach, he's my coach and my dad." Troy said.

Jason stood up, "I'm gonna go get a new paintbrush. This one's messed up." He went up the stage and got a new one and once he was about to leave he bumped into someone immediately causing that person to drop all the papers they were holding, which was quite a lot.

"Sorry about that." Jason apologized as he crouched down and gathered all the papers. He handed them back to the person and it was a short girl who had her hair tied in a bun and was wearing glasses.

"It's okay. It happens a lot." The girl said as she took her papers from Jason, "I'm Kelsi. I'm the composer for the play. And you are?"

Jason was too busy staring at her that he completely drifted off, "Oh I'm just here for detention. You're a composer? That's cool"

"Yeah. This is actually my first time composing the play." Kelsi answered, "It was nice meeting you Jason. Hope to see you at the play." Kelsi waved goodbye and walked away. Jason smiled and returned back to where Chad and Troy were talking.

"How about a bet Troy? If you manage to melt the Ice Queen's icy heart I will run around in a dress during practice. And if I win you'll be the one wearing the dress." Jason overheard Chad saying.

"Whoa. What's this about a bet?" Jason asked as he joined the two.

" I told Troy that if he manages to snag a date with Sharpay Evans I'll run around in a dress during practice." Chad told Jason.

"But Sharpay hates Troy."

" Exactly. Which is why he will never be able to do it."

"Fine if you think I won't be able to get her to date me just you wait and see." Troy agreed to the bet, "I'll pick out the dress you'll be wearing myself.

"Deal." The two shook hands.

"Guys are you sure that this is a good idea sure she's not the nicest person in the world but she still has feelings." Jason asked them.

"Cmon Jason she's a total witch. Everyone in this school wants to see her be knocked down on that high pedestal of hers. We'll be doing everyone a favor."

"I guess." Jason hesitantly agreed.

"This will be just our secret if anyone finds out about this and someone tells Sharpay then I won't have a chance." Troy asked the two.

"Sure." Chad and Jason agreed and from then on the bet had begun.