"Wow Sakura, you really have changed!" preened Naruto tousling his hair.

She looked down and played with her feet. "You mean it?"

"Er . . . yeah, I mean it", he twisted his body in all kinds of awkward contortions. Did she really believe him or was she just playing along? Naruto knew something big was coming. Because whenever Sakura had that look in her eyes, that glint, the next thing she did was anything but normal.

"You know what Naruto I'm in a good mood" she said, leaning against a trash can to the nearby restaurant. His body rigidified as he braced himself for the bomb. Orochimaru had nothing on this girl.

"How about. . . we drop this little act and go on a date"

"Yes! I knew you would fall for me eventually . . . there's a catch isn't there?" he quipped, practically salivating.

"Nope. . . no catch", he leaned over to hug her but instead hit his head as she sidestepped. "Well, there is one little catch" she teased, biting her nail.

Groaning, Naruto stood awaiting his mistress orders.

"In the next twenty-four hours I challenge you to go on as many dates as you can. If you happen to go on more dates than me- you win!" The fighting spirit boiled within him. It was a contest all their own. A battle of resolve not even Sasuke could provide.

"Isn't that crossing some kind of morale boundary Sakura-chan?" he remarked, finally realizing why he liked her so much.

VVVV

There were twenty or so girls in their late teens gathered round the coffee shopped. Half of which Naruto already asked out.

"That's a nice necklace, it goes really well with your shoes" said Naruto through his teeth.

She disfigured her face like she had tasted something sour "Are you gay?" replied the girl with lollipop hair as she continued walking her dog. Giving up was not an option! No one said it would be easy.

He stabbed his elbow into the nearby table where an attractive brunette sipped her cappuccino with delicate fingers. "I'm Naruto Uzumaki! The coffee here is good huh? I never tried the cappuccino."

She giggled into her hand. "Well Na-ru-to, you should. It melts on your tongue, especially the caramel"

He smiled dumbly. Now was his chance, now or never. "I have an idea, why don't I buy one and we could drink it together" his smile was ear to ear.

She took a sip through her thin lips. "Ok, let's do it" she purred. The coffee lover's short friend eyeballed Naruto, frowning and twisting her hair. She whispered something in the brunette's ear like a demon while pointing at his headband accusingly.

"I don't date ninja" the coffee girl said plainly

There was a jolt of pain in his chest while his hands went clammy. "Ok sorry to bother you" said Naruto rubbing his head. He drifted away half-mindedly. This bet left flames in his stomach, but if he couldn't win a measly bet how did he expect to become Hokage?

VVVV

"You look terrible" shot Shikamaru, straightening his ponytail

Choji who was behind him tore apart a bag of potato chips with his teeth grunting in agreement.

"There must be something wrong with me" he admitted grasping his shoulder.

"I know where you can get a ton of girls" Choji sneered.

"The Red Lantern District doesn't count Choji, they're paid to do that" said Shikamaru, then spitting into the trash can to scrap the bad taste it left.

Naruto thrust his tongue against his cheek before speaking, "You must know a lot about girl's Shikamaru, train me".

"Oh THAT kind of training" said Shikamaru putting his hands up like a shield. "Women are such a bother, find someone else"

"Ok Choji you train me"

Shikamaru quivered like a knife thrown against a dinner table. "That won't be necessary" he chided pushing his unenlightened friend somewhere "you can have my share of barbeque Choji" he added.

VVV

The man in the accomplished vest took a sip of coffee under the candy-cane umbrella before saying "I never expected you to go player on me"

"It was Sakura's idea!" informed Naruto, pacing like a wind-up toy.

"Oh brother, I know what this is about" he scoffed resting his back on the chair. His beady eyes searched for targets. People he thought Naruto would stand a fighting chance at snagging. They were like dolls most of them, though a few had sincere faces he didn't mind taking a second glance at.

"Its no use" he concluded.

"Never give up Shikamaru!"

"That's not what I meant" he flicked open a cigarette lighter and Naruto was lost in the flame. "We're going to make this one an inside job"

VVVV

"Ha, ha, someone's in trou-ble" jeered Ino, as she bounced on her queen-sized bed.

Sakura untied her scarlet ribbon and her pink hair flowed like a silk river. "It's not funny pig; the kunoichi rite of passage is serious stuff. If I don't go on at least three dates-"her heart sunk "I'll have to give up on being a ninja forever"

Ino bounced over to Sakura with her brush "I don't know what you're so worried about. Only a truly ugly girl wouldn't be able to-"she stopped brushing "I see your point".

"Damn it sometimes I wonder why I still hang out with you!" she said with eyes of murder. "By the way how many did you get?"

Ino paused for effect

"Twelve"

"Twelve. . . you pig" that word carried more of a sting that time.

Secretly Sakura did envy her accomplishment, but through pouty lips and crossed arms the truth would never be told.

"Aren't you worried what people think of you?" Sakura queried.

"No, the thought never crossed my mind" said Ino with a blank face.

"Well I am, so I took some measures"

Ino's eyes lit up and she stopped brushing.

"I made a bet with Naruto. He thinks we're having a contest!" she couldn't control the giggles it entailed. "He probably won't find a single date but at least he's out of my hair!" her voice cracked again and she thought she might die from laughter.

"Oh" said Ino. She packed some things while Sakura rolled on her bed. Dressing in an eye catching shirt with blue-jades it was obvious she was thinking about something.

"H-hey where do you think you're going?" demanded Sakura as she came back to reality.

"I'm going to be Naruto's first" she declared.