"I would like you to ask me out on a date."

Naruto choked on his ramen. His eye snapped to Sai and that forced smile she always wore. Behind him, he could hear Sakura's chopsticks drop to the counter. It was just supposed to be a casual Team Seven get together. "What why?"

It wasn't that Sai was unattractive. She was probably prettier than Sakura and he might have found the way she had her stomach exposed sexy. But any chance of romance was shot down within minutes of talking to her.

"Well you're a boy," She poked him in the chest. "And I am a girl, is that not why you ask Sakura out all the time?" Sai paused as she considered the fact her book said that boys were the ones to ask girls out they liked. "Unless it's just that you don't like me Naruto."

"What no! That's not it at all!" Naruto waved his hands frequently Sai almost sounded hurt at the thought that he didn't like her. "You're one of my friends Sai and a member of Team Seven! Of course, I like you. I just don't like you how I like Sakura!"

"Leave me out of this." Sakura wiped her mouth with the ramen she had to spit up at Sai's sudden declaration. "Honestly Naruto you should take her up on that offer it'd be good practice for both of you."

Naruto stared at Sakura with his mouth wide open. How could she do that to him! Did their years of friendship mean nothing? She was supposed to be his sidekick! He turned to see Sai with a confused look on her face.

"Is there a difference in how you like me and Titless? You should like me more than her anyways. my boobs are bigger." Sai stuck her chest out to emphasize the size difference.

Sakura had to get a new set of chopsticks as hers suddenly exploded.

Naruto aware of the growl Sakura was making at Sai's comments tried not to look at Sai's chest. "The difference is that Sakura is Sakura and you're Sai, I've liked Sakura for a long time and I think she's pretty."

Sai pondered this for a moment before she snapped her fingers. "Oh, so you like Loli Tsundere!"

They were going to die. Wait, where was that looming sense of doom that always followed whenever sai said something incredibly stupid around Sakura? It was like she had less survival instincts than he did! Which was saying something? Naruto looked to Sakura who was staring into her bowl of ramen, her face free of rage just confusion.

"Why do I feel like if I knew what that was I'd be really mad at you?" Sakura blinked at her ramen. With a hapless shrug, she began to stir her ramen, cooling it slightly. "Because it's the holiday's and I fully support you two idiots dating I'm not going to ask what it is."

"Oh, a loli is a-" Fortunately for Sai naruto's hand was slightly faster than her mouth.

He got in close, those cold eyes of hers raised in confusion. "If you promise not to explain what either of those things are to Sakura I'll go out with you, okay?"

She blinked, her long eyelashes fluttering ever so slightly. Then after what seemed like an age, she nodded.

"I now pronounce you man and wife," Sakura grumbled after a long slurp of noodles.

"Aren't you at least a little concerned that I'm going out with someone that isn't you?"

"Nope, if anything I'm relieved that you won't be asking me out anymore and that Sai will have someone else to infuriate." Sakura gave him that fake overly cheerful smile that was at least half bullshit. "I'm rooting for you two!"

"Well I have a full shift at the hospital, so you two have fun on your date." With that she slapped her chopsticks on the table, her ramen bowl empty. She paused at the threshold. Her smile turned malicious. "Oh and I'm going to find out what a loli tsundere is so… yea."

They were dead so very very dead! And it wasn't even his fault this time! "Do you really not have any sense of self-preservation?"

"That's a big word Naruto," Sai removed his hand from her mouth, her lips forming that well-practiced smile she liked to wear. It was n the painful side of fake, nothing like her real smile that could sometimes be seen, like cracks of like in an old building.

"Oh shut up, Iruka has been making me study so that I don't sound like an idiot when I'm the Hokage."

"But you are an idiot." She smiled, reaching over to give him a light shove. "Well if you ever need help don't be afraid to ask me, I'm quite good at reading."

Naruto slammed his head onto the counter and let out a long healthy groan. How on earth was he going to survive a date with Sai? No matter how attractive she was the woman just thrived off of his misery. "I can't believe I have to date you."

"Speaking of that, you haven't asked me yet," she smiled brushing a bit of her long hair away, showing off her perfect ear and the tender nape of her neck. It was one of the few moments where her natural beauty shined through. Shame she only showed it when she was tormenting somebody.

"Ask you what?" Naruto sat up, trying not to stare at Sai. Dammit, she just had to be so forward about everything! Not that he wasn't forward… he just had… well, he didn't have tact… he… she was just far to blunt!

She gave a soft laugh and blew on her noodles. "Ask me out of course."

Naruto's mouth fell open. And the words died in his throat mostly because Sai began to eat noodles in the sexiest way possible. She slowly took them into her mouth, humming in delight, eyes closed shut before she began to slurp the stragglers up. Great! Why on earth did she suddenly become extra attractive now that he knew she wanted to date him?

Apparently, he was that desperate.

"Wait, wait, wait." Naruto held up a hand and pinched his nose. "You want me to ask you out on a date?"

"Correct."

"And you're going to say yes?"

She paused, that was a great sign! "I haven't really thought about it, I suppose it depends on how you ask me."

Was this what hell felt like? "So you want me to ask you out on a date, but you aren't sure if you'll say yes or not?"

"Correct."

"Guh." This girl was going to be the death of him. He really couldn't believe he was going to do this. It was basically scheduling a time for a headache. "Fine, Sai will you go out on a date with me?"

She snorted. "Not if you're going to ask me like that?"

"Wait, what? How am I supposed to ask you?"

Sai pulled out a book and shoved it into his chest. It was titled 'How to date for dummies'. "That's the book I've been reading about the subject, read it and then come try again."

"I'm not going to read a book just so I can date you!" It didn't stop him from looking at the book. He really shouldn't be surprised that it was written by Jiraiya. The only reason why it shouldn't be burned was the respect he still had for his former teacher.

"Oh," She looked sad. In the most pathetic way possible, if she was next to a freshly kicked puppy, the puppy would feel sorry for her. She stirred her ramen, cold dead eyes losing their focus, soft pink lips slightly parted small frown. Her hand drifted across the countertop and touched his. "But, you said you'd date me if I didn't tell Sakura what a-"

"Okay fine, I'll read the book then ask you out, but if I do what the book says you can't say no again!" Naruto flailed his arms wildly.

"Excellent, I look forward to it."

His ramen was cold. How on earth was he distracted long enough for his ramen?

XXXX

Naruto sank into his couch glaring up at his ceiling, most of his time was already spent plowing through books and taking tests while Iruka lectured him. Why can't he just jump from Chunin to Hokage? That's what Gaara did and that worked just fine.

But now he had to spend what little free time he had to read a book he didn't want to read to go on a date with Sai he didn't want to go on. "Might as well get this over with."

It was written by Jiraiya at least so the book had that going for it. The cover was yellow, with two overly cartoonish figures on it with hearts in their eyes.

"Chapter one," Naruto began, his eyelids already began to droop. "Gauging their interest. The first step to dating someone is to find out if they're actually interested in dating you, now I'm not telling you to ask them, that's has a solid chance of backfiring in a spectacular way. Instead, there are two subtle ways that we as humans show we're interested."

"First, is how often they touch you. Do they stand close to you so that you're constantly bumping into them, or do they stand off to the side arms closed in and trying to avoid contact at all costs? If it's the former you're in luck! The later can be a bit confusing given the type of person they are."

"How often she touches me huh?" Naruto closed his eyes and tried to remember the last time Sai touched him. She touched him a few times when they ate ramen right? Once when she touched his hand, she also poked him in the arm. And what about Sakura? The only time she touched him was during punches, headlocks, and other times she was trying to maim him.

"Sai Touches me a lot," Naruto frowned. "She probably started doing that after she read the book."

"The next way is how they look at you, is it full of disgust, do they smile, or is their face a neutral mask. Smiling is a great way of telling someone that you like them without even saying words. While a frown is a great way of telling people to piss off. Again, lots of smiling is a good sign that they are interested in you. However, there are cases where depending on the type of person that frowning or indifference might also mean that they're into you. Especially if they tend to hit you a lot in such a way, this type of behavior is often referred to as a Tsundere."

Naruto groaned, There was that word again, one that nearly cost him his head. And made his ramen cold. "Wait!"

He sat up and reread that paragraph. "No wait, there's no way that Sakura would have feelings for me, she's after Sasuke after all. Besides what would Jiraiya know? He couldn't get Tsunade no matter how hard he tried."

He flopped back down, his eyes straining.

"Now I hope you've figured out how if they like you or not." He had no idea. "Now for the tricky part in how you interact with them. Look directly at them, men that means no staring at their cleavage while she trying to talk to you." Naruto blinked and made sure he was reading it correctly. Did Jiraiya just write down not to be a pervert? "That might be the first clever smart thing that's been in this book."

"And Ladies, if you put the girls on display don't get mad when he gives them fair tribute it just means he's interested."

And he ruined it.

"Next blah blah blah, be helpful, Sai did that, I do that blah blah blah, Make sure I bath, and smell nice. Approach her, blah blah blah, small talk blah blah blah. Timing is everything, make sure that you're asking them to something you're both interested in."

Now there was part of the problem, he had no idea what Sai liked! Or even if they had similar tastes! Sai liked art. And he … kind of liked art? He thought it was cool and all… but there was just no way that he could stare at paintings all day and not be bored.

"Be confident blah blah blah, I'm Naruto Uzu-fucking-maki next Hokage, got plenty of confidence and I don't actually like Sai so I have no reason to really worry, and be prepared for rejection, well… she did just reject me earlier. If she doesn't it again I'm not going to ask her out again."

Now he had to actually plan a date. Great just great.

AN: Remember how I said a long time ago I'd do a fem Sai fic? well hey look! fem Sai! Welcome to By The Books where Sai forces Naruto to go on dates and read books about dating.

Anyways! happy holidays! and I hope you enjoy this chapter/fic