Disclaimer: I don't own Naruto...

A/N: I came up with this idea when I was typing something else about Kurenai and I was mentioning about her being the "Ice Queen" of Konoha. Btw, Naruto and the others are 17 in this story while Kurenai will be a little younger, 25. Romance MAY be hinted but the full romance scene will be in the last chapter... or second last.

I Will Win This Bet!

Chapter 1: "The Bet & Getting Information"

"I'm telling you! Sensei likes Anko-san!" Inuzuka Kiba's voice reached Uzumaki Naruto's ears. Naruto had been walking around aimlessly searching for something to do and now just seemed to be the thing.

"Kiba," Shino's dead serious voice came next. "Anko-san is Kurenai-sensei's friend."

"But she's never ---"

Naruto chose that moment to jump down from the tree above Team 8 which he'd snuck into. "Hey, what's up?" He yelled cheerfully.

"N-naruto-kun..." Hinata blushed at the sight of her crush.

Naruto gave her a foxy grin which made her blush even more. He was completely oblivious to it though...

"Naruto!" Kiba grabbed Naruto by the shoulder unexpectedly and pushed him in front of him so that Naruto was facing Shino. "Back me up, man! Shino won't believe me that Kurenai-sensei isn't straight."

"Sensei is straight. She is with Asuma-san." Shino replied with his usual monotone.

Kiba crossed his arms over his chest, "Sensei and Asuma-san aren't dating, they just hang out alot. You just haven't seen her with Anko-san! Akamaru and me saw it, right Akamaru?"

Kiba's dog yipped in response.

"I've seen Kurenai-san with Anko-san before," Naruto spoke up. "But I don't think there was anything between them."

Kiba's jaws dropped slightly. "You were supposed to help me, not him!" He pointed at Shino. "Fine then, prove to me she's straight." The last bit was directed at Naruto.

"How could I do that?" Naruto scratched the back of his neck. He wasn't exactly taking Kiba's challenge seriously. "Well, anyway, it's lunch time, I'm going to get some ramen. See ya." Naruto waved while walking away.

"Naruto, wait!" Kiba yelled. "Let's have a bet on this!"

Naruto turned around but didn't seem to be taking it seriously.

"Unless you're too scared to." Kiba added. Now that would motivate him...

In less than a second, Naruto was standing in front of Kiba, staring intendly at him. Kiba grinned at his success while Naruto asked, "So, what is it?"

Kiba thought for a second before answering, "You have to get Kurenai-sensei to date and kiss with the same guy, any guy, in Konoha to prove she's straight within five days. If she dates Anko for some reason, I win and you're not allowed to tell her about this bet to get her to date someone."

"And what if I win?" Naruto asked.

"I don't know, choose something."

Naruto stood there for a few minutes, deep in thought. Now what would he make Kiba do? An image of Tsunade popped up in his head. Then he smirked evilly resulting in Kiba staring at him nervously.

"You have to ask Tsunade-obaa-chan to see her oversized breasts!" Naruto said, grinning.

"What!" Kiba exclaimed. That was seriously not what he had been expecting.

"Too chicken?" Naruto teased, still grinning.

"Feh, no way. I'll do it." Kiba responded and then added. "But if I win, you can't eat ramen for three months."

"What!" This time it was Naruto's turn to yell out in shock. NO RAMEN! NO RAMEN!

"Too chicken?" Kiba was the one to say it this time.

Naruto huffed and crossed his arms but gave him a defiant glare. "I'll take your challenge."

Day 1 of the Bet Starts : Destination Kakashi-sensei

"Kakashi-sensei!" Naruto ran up to his former sensei who was currently sitting under a tree, reading his usual Icha Icha Paradise.

"Oi, Naruto." Kakashi greeted Naruto, looking up from his book briefly before turning back to it.

Shino, Kiba and Hinata were hiding in a few bushes in the distance, observing everything Naruto was doing. Kiba insisted that Naruto may try to cheat so they'd have to watch his every move.

"Kakashi-sensei, what do you know about Kurenai-san?" Naruto asked.

Now this caught Kakashi's attention. He closed his book and a glint appeared in Kakashi's eyes... err, eye.

"So..." Kakashi said in his sly voice with his eyes half closed, looking at Naruto with that look. "Why do you want to know something about my fellow Jounin, huh?"

It took Naruto a moment to register the way Kakashi was staring at him and the way he'd asked that he realized what Kakashi had meant.

"Nooo, noo!!" Naruto frantically waved his hands in front of him. "It's not like that! I just need some information for..."


"...For a bet!" Naruto finished.

Kakashi stared at his former student suspiciously, "What kind of bet is it, Naruto?"

Naruto quickly explained to Kakashi the bet he and Kiba were having. He also told Kakashi not to tell anyone or Kurenai might find out.

"Mm... I don't know as much about her as Asuma or Anko." Kakashi said.


"She's honest, plain but sexy, and..."

Naruto sweatdropped, "Kakashi-sensei, what I meant are the things she likes, not how she looks. I already know how she looks like!"

"Ahh..." this time it was Kakashi's turn to sweatdrop. "To be honest, I don't know what she likes or dislikes."


Silence. And then:

"Kakashi-sensei! She's your colleague but you don't know what she likes?" Naruto yelled out comically, stomping one of his foot on the ground. He really looked like his 12-year old self when he did that.

Destination Asuma-san

"Asuma-san!" Naruto ran over to Asuma who was standing against a wall of some building that didn't seem to have any occupants.

Asuma greeted and Naruto and then asked, "So what brings you here, Naruto?"

"Well..." Naruto felt a little nervous to be asking Asuma about this. He didn't know why, but he felt much more comfortable about telling Kakashi. And even though Naruto was pretty tall for his age, 175 cm, Asuma still seemed to be much taller and looming over him... Right now, he was trying to ask this 'giant' about something that he hadn't even asked Kakashi since his sensei seemed to be clueless about Kurenai.

"Hmm?" Asuma said.

"Does Kurenai like men?" Naruto got straight to the point.

Asuma almost spit his cigar out of his mouth, but regained his composure quickly. A light blush tinted his face. It was pretty obvious that he liked her... but she seemed to be oblivious to it, much like Hinata's affection for Naruto. And even though this wasn't directed at him, he still found himself turning slightly red.

Suddenly, Naruto had a huge grin on his face and Asuma raised an eyebrow.

"You like Kurenai-san, right?" Naruto yelled quite loudly. Too loud. Good thing no one was near them.

Asuma was about to say something when Naruto cut in, "That's great, Asuma-san! I'll help get you two together!"

"Ehh...uhh...w-WHAT!" Asuma sputtered. He usually didn't sputter but... what the hell was the kid saying?

Naruto gave Asuma another one of those foxy grins and then said, "Leave it up to me, Asuma-san! I'll arrange a date for you two tomorrow evening. I'll see you tomorrow at six o'clock at the place beside Ichiraku! Ja ne." And with that, Naruto disappeared with a 'poof!' leaving a bewildered Asuma standing there, staring at the spot Naruto had just been standing at.

Destination Kurenai (Observing AKA Gathering Information)

Kurenai was currently eating ramen at Ichiraku's, something she rarely did. She was just getting a quick lunch.

Naruto was perched on top of a building across from Ichiraku's. Right now, he needed to gather as much information on her as he could to make Asuma's date a success. After he was done observing, he would ask Kurenai to go on a date with Asuma.

Kurenai was wearing her usual outfit, white wrapping and a red sleeve on one arm. Naruto decided that she'd definitely need a different outfit for a date. 'She's pretty.' Naruto thought. 'It's no wonder Asuma likes her.' Kurenai finished her ramen and began to walk away, with Naruto trailing around 25 meters behind her.

It was after a while of following that Naruto realized they were in a forest. Kurenai began to speed up her pace and so did Naruto. He was curious to where she was heading. After a while, Kurenai's speed was more of a sprinting speed, except that they were jumping from tree branch to tree branch. Suddenly, there were kunais flying at Naruto from the front which he expertly deflected with his own kunai that he'd grabbed from his weapon pouch.

Naruto sensed something coming from above and when he looked up, he could make out the shape of a person... attacking him with a kunai in hand. But too bad, Naruto was talented. He quickly made a Bunshin which he threw toward the person. It connected with the kunai, resulting in a puff of smoke which served as a distraction. When the smoke cleared, Naruto had disappeared from the spot he had just been a few seconds ago. There was a yell, which came from Naruto and the next thing the person knew, the attacker was pinned under Naruto with a kunai at the neck.

Both their eyes widened. It was Kurenai who was under him!

"Naruto?" Kurenai said.


"AAAAAHHHHH!" Naruto practically jumped into a nearby tree (okay, not really) when he realized he was on top of her.

- - - Tick Tock Tick Tock - - -

"I'm sorry." Naruto grinned sheepishly at the kunoichi in front of him while scratching the back of his neck again. A habit was a habit. 'Damn it, I just had to embarrass myself in front of such a hot... AGH, I did NOT say that!'

Okay, Uzumaki Naruto was a guy, so he must have some hormones...

"It's okay, Naruto. I was the one who attacked first, I'm sorry." Kurenai said.

"Don't say that, Kurenai-san!" Naruto waved his hands in front of him. "It was a natural reaction since I was following you. You don't need to be sorry." 'And besides, I got to land on top --- Damn it, SHUT UP!'

Kurenai smiled. He was pretty nice. "So Naruto, what were you doing, stalking me?"

"Ehehe," Naruto thought she was exaggerating the word 'stalking' a little too much... It was embarrassing him. Now, how should he phrase his next sentence? "What do you think of Asuma-san?"

"Asuma?" Kurenai was taken aback by Naruto's question. "He's a great friend, though I wish he wouldn't smoke that much. He's killing himself."

"So... would you consider a date with him? Maybe tomorrow evening?" Naruto asked hopefully.

"Huh? I, uh..."

She trailed off and when she didn't answer for several seconds, Naruto came closer to her. Suddenly he wrapped his arms around her shoulders and her back, pulling her against him. Now that she was leaning against him, Kurenai blushed furiously. Naruto then put his mouth right next to her ear, "Tomorrow evening beside Ichiraku's ramen stand at 6 o'clock. Wear something nice." He pulled away right after that and then disappeared in a puff of smoke, leaving a shocked Kurenai standing there.

He hadn't even given her a choice!

A/N: Uhh, I hope that didn't turn out too badly... There will be around five or six chapters in total. Please review and tell me what you think! Should I continue this? Cuz... I dunno, maybe this idea was lame... I hope not though. By the way, this is a Naruto/Kurenai fic even though their romance won't be shown until later chapters. There may be hints along the way, but the full romance chapter will be the later ones.

Well anyways:

Next chapter:

-Asuma's date with Kurenai-... But in order for Naruto to win the bet, he needs to get Asuma to kiss Kurenai! Can he do that? If he can't, the plan fails. What else can he do? But nothing failed/succeeded yet until the next chapter is up! Oh yeah, any suggestions on what Asuma and Kurenai should do...? Or where they should go? I'm not exactly good with these things...