Disclaimer: I don't own Naruto...

'Blah' -- Naruto talking through the radio ear-phone thingie.

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I Will Win This Bet!

Chapter 2: "Plan 1: Asuma and Kurenai's Date"

... 5:45 pm...

"Naruto, are you sure this was the best outfit?" Asuma was definitely nervous.

Naruto just smiled at the man and said, "It's nice! Nice t-shirt along with nice pants. Anyway, Asuma-san, I'll be helping you with the date just in case." He gave Asuma a pair of radio ear-phones (not the huge ones, the tiny ones). "I can hear whatever Kurenai-san says and I can tell you what to say or do just in case you're too nervous. After all, I do want this to be a success." 'I won't be able to stand not eating ramen for a whole 3 months...'

Asuma nodded and Naruto went into another nearby restaurant where Kiba, Shino and Hinata were.

"I can't believe you were able to get Kurenai-sensei to agree on the date." Kiba glared (not angrily though) at Naruto. "How did you do it?"

Naruto grinned, "I have my ways."

What a nice way to end a conversation.

... 5:59 pm...

Kurenai finally arrived at 5:59. One minute before their scheduled time. She had been so occupied with changing and fixing up her hair that she'd almost forgotten the time. Good thing she remembered. Right now, she was clad in a white tank-top which fit her so that her perfect figure was shown quite clearly. Along with the tank-top, she wore a dark red mini-skirt that reached down to her lower thighs. It revealed her legs perfectly.

Team 8 and Naruto stared at the sight.

"I never realized Kurenai-sensei was so hot." Kiba muttered while Akamaru yipped quitely in response.

Naruto blushed at the thoughts he was having but quickly shook them away. Having trained with the Ero-sennin for two and a half years had made him have some perverted thoughts once in a while.

Asuma was staring at Kurenai all the while she walked toward him. Even when she was finally standing in front of him, he didn't say anything.

"Yes...?" Kurenai spoke after a while of silence.

Asuma looked sheepishly at Kurenai. 'Tell her she looks good in that outfit.' Asuma heard Naruto's voice in his ear. Argh, why did he have to be told to say that? Was he really that nervous as not to think of saying such a thing?

"You look nice in that." Asuma commented.

"Thank you," she smiled and then asked. "So... where are we going first?"

"Would you like to see a movie first, or get something to eat?" Asuma held up two slips of paper. "I bought tickets already by the way."

"I don't usual eat dinner this early. Let's go see the movie."

"Alright." He and Kurenai began walking. "The movie is at the 'Konoha Movie Theatre'."

Kurenai nodded and then Asuma heard Naruto's voice from the earphones. 'Asuma-san, Team 8 and I are following you guys. And by the way, you should eventually try to hold her hand, it's more romantic.' In the background, Asuma heard Hinata say something which he couldn't make out.

... 7:14 pm -- after the movie...

"Let's get something to eat." Asuma suggested right after the movie finished when he and Kurenai were outside. Kurenai nodded in response so Asuma continued. "Which restaurant would you like to go to?"

Kurenai just shrugged. It didn't really matter to her since she wasn't all that picky. "Any is fine."

'Asuma-san, the one to your left is a good one.'

Asuma quickly turned to his side to see one of the best restaurants in the village. Damn, this was going to cost him a hell lot of money, but hey, it was a date. 'For a date with Kurenai, it's worth it.' Then he voiced out, "How about that one?" He pointed toward the restaurant Naruto mentioned.

"Things in there are expensive, are you sure?" Kurenai eyed the outside of the restaurant. Even the sign indicated that the restaurant itself was a five-star.

"Yep, let's go." Asuma said.

... Half an hour later: 7:50 pm...

They were now finished eating their meals, and both were full. Just like the restaurant's rating said, the food was delicious. Kurenai and Asuma ordered two drinks (not sake) after dessert was served, which had been equally delicious.

A few tables away, Kiba grumbled, "Ugh... damn it." He put his head down on the table in frustration.

"What's wrong, Kiba-kun?" Hinata looked at her teammate worriedly.

"He's brooding 'cause he's losing the bet." Naruto answered the quesiton for him.

"You haven't won yet though." Kiba lifted his head to glare at Naruto (not in an offensive/angy manner though).

Naruto chuckled and replied. "Oh, you mean the kiss. Don't worry, they'll be kissing in no time." There was a cough heard from Naruto's earphone and he realized Asuma had heard what he'd just said. "Haha, am I embarassing you, Asuma-san?"

Now, back to Kurenai and Asuma, who were 'talking'. "So..." Kurenai began. "Did Naruto set this up?"

"Huh?" Asuma had only the faintest idea of what Kurenai was talking about, but he hoped it wasn't...

"I mean, people always take our friendship the wrong way."

'No...! She thinks it's a set-up.' Asuma thought.

It was true what she said though. Everyone thought Kurenai and Asuma liked each other. Their friendship, which had lasted from their academy days, was taken the wrong way. Well, for Kurenai it was taken the wrong way, but in Asuma's case... He really did like her in a romantic way.

Asuma was about to speak up to tell Kurenai so, but she interrupted. "Do you find it annoying?" She asked him.

"I, uh... " he trailed off when Naruto spoke through the ear-phones. 'Asuma-san! Tell Kurenai-san that it wasn't a set-up. It --' This time, Asuma cut Naruto off by saying, "Sorry Kurenai, I have to go the bathroom."

Once out of view and ear-shot from Kurenai, Asuma said, "Naruto, she doesn't like me." It was heartbreaking how Kurenai had said the words, 'People always take our friendship the wrong way.' 'She only likes me as a friend...'

'What are you talking about, Asuma-san?'

Asuma remained silent. If he talked about it, he would really want to cry. Crying was not something he ever did, it was too out of character for him. But when it came to romance... Well, anyway, right now he needed to get back to the table.

Once he got back, Asuma hesitated a moment before saying, "Well, to answer your previous question, I don't mind if they take our friendship the wrong way and set us up once in a while. It's enjoyable anyway."

'WHAT?' Naruto's too loud voice in Asuma's ear made him cringe. And since Naruto was a few tables away...

Oh boy.

"Naruto?" Kurenai asked. Okay, this was going to get complicated.

Naruto nervously turned around to face Kurenai and Asuma's direction. Had it not been such a serious moment, Naruto would have slapped his forehead over and over.

"Phew, I'm saved." Kiba said, wiping imaginary sweat from his forehead.

"Nooo..." Naruto moaned with exaggerated gloominess. "Asuma had the best chance out of everyone."

Shino remained quiet.

"Naruto-kun, I'm sure you'll find another way." Hinata spoke softly, trying to cheer her crush up. "You still have four more days."

Naruto was still trying to think of a new plan. What else could he do? He had thought for sure that Kurenai liked Asuma.

"If that didn't work... maybe I could use a henge."

Naruto sat up suddenly at his idea, but then layed back down.

"I could use a henge and make myself look like Kurenai-san. Then Kiba, Shino and Hinata-chan would think I'm Kurenai-san." His mind wandered off to the guy he'd date and that's when he realized something and groaned. "But I'd have to kiss someone if I used that technique. Nooo, I can't do that."

When Naruto drifted off to sleep that night, he had one thought in mind, "Ino..." There was something about her that he couldn't remember. He knew that she had something that would be able to help him but still couldn't remember. Not until morning came.

This chapter is more of a filler chapter or something. Something that'll fill up the time between the 5 day time period. I've also decided that full romance with Naruto and Kurenai will be in chapter 4. So um... look forward to that (lol).

Next Chapter:

-Naruto seeks Ino's help-... Naruto gets Ino to help him with a new plan he's formulated. This time, the succes rate seems to be higher, but there are certain obstacles. Obstacles like one named 'Kiba'.