AN: An update after five years? Stranger things...

This fic has some wonderful fanart, which you can see on my tumblr (under the same name!)

Ino laughed for a solid ten minutes as Sakura regaled her with the look on Kakashi's face. Even Tsunade had let her off with nothing more than a crisp cuff to the back of the head after his Benz disappeared around the rainy corner. It was, Sakura decided, permission to proceed as she wished.

"Serves him right," Ino judged, speaking around a mouthful of hair pins. "I bet he was speechless."

The blonde bombshell was a familiar sight in the compound. They'd been friends for years, growing closer now that Sakura's father had finally abandoned her to the family business. It helped to have someone close to her own age, though Ino had lived a very different life before coming under Tsunade's wing.

"Nasty Konoha bastard," Ino continued.

"You saw him for thirty seconds."

"Enough to figure him out, babe." Ino winked at her, sliding the last pin into place in her intricate updo. "Ya forget it's my job to do that."

Her confidence rang true: Ino was the top earner at the Senju's most exclusive hostess club, the kind of joint frequented by men who had their names in the papers every morning. Half the Senju compound was in love with her and the other half at least interested, a fact which amused the two young women every time a rich-boy patron tried his luck. Their methods were a far cry from the wooing employed by the yakuza: love confessions straight to the face, usually over a heated game of cards. Often, they'd get a tattoo representing their feelings.

A drunk guy stumbling around with his daddy's money had nothing on that.

"Did you find out what age he is?" Ino asked, standing up and stretching the kinks from her spine.

"The Nidaime won't tell me," Sakura grumbled.

"Which means he's at least ten years older."

"And no more than twenty."

Ino snorted. "Yeah, I don't think that'll happen again. I'll never forget the look on Jiraiya-sama's face when they sprung that old fish on you."

Sakura shivered, fingering the Senju scarf still wrapped around her neck. Her grandfather in everything but blood, Jiraiya was the very picture of easy going fun until he wasn't. If Tsunade was the flash flood, Jiraiya was the brewing storm. Sakura had barely believed his reputation until the clan elders had arranged a marriage meeting between her and a grizzled yakuza a handful of years younger than her grandparents. It had been frightening, truly frightening. A baptism of fire into the heart of the underworld lifestyle, with men three times her age offering severed fingers in apology while her normally jovial grandfather watched with a face like thunder and hands curled into fists.

No. The clan wouldn't be trying anything like that again, impending troubles or not.

"If anything, this Kakashi comes highly regarded by jii-chan, which I'm not sure I'm all that thrilled about."

Sakura followed Ino's lead as the other woman left her bedroom, suppressing a snicker at the way her bodyguards trailed after her friend with their eyes. She knew they drew lots for duty on nights when she and Ino hit the town.

"I think he's a fan of those awful books jii-chan writes."

Ino laughed again, hand to her throat. "They're funny! You should read them."

"I'm sparing myself from the details of my grandparent's sex life, thanks very much."

Rolling the beautiful blue eyes that were her greatest money makers, Ino led them down the still-wet path of the front garden towards the waiting Mercedes. Hopping in without waiting for the junior yakuza at the door to open it, they chatted about matters less offensive to Sakura's ears as the car slunk towards the Kita district. Ino's position as number one allowed her a few evenings off a week and Sakura had little to do after dark, which left them free to hold court in Shikkotsu's nightlife district whenever they tired of the compound.

Sakura watched as the city came into view and the streets grew busier. It was shaping up to be a good evening - they'd been invited to three or four separate gatherings, all of which were populated by people they enjoyed spending time with, and one of which was run by people who owed the Senju clan a rather large favour. The plan was to start with the former and end up at the latter, a neat plan that would see them sufficiently drunk with minimal fuss (and minimal card charges).

"Anyway…" Sakura sighed, "I don't understand why the Uchiha group didn't send one of the Sandaime's sons today."

"One of his sons - Sakura, don't pretend you are talking about anyone else but Uchiha Sasuke."

They shared a look before Sakura shrugged.

"His beautiful face aside, Ino, it makes sense," she explained. "I'm the next head of the family, and with Itachi-san set to become the Yondaime after his father, Sasuke should be looking for an equal position."

"You do have a point… it would be a win-win for the Uchiha, having two sons in charge of different prefectures."

Sakura held her hands out, palms up. "Close enough to ally but not near enough to feel the need to jostle, you know? It's enviable."

"Well, maybe that's why he's sent Kakashi-san instead."

"Kakashi isn't the Sandaime's son."

"No, but he's almost better in a way," Ino said thoughtfully. "The most loyal of loyal clansmen, bound by oaths rather than blood. It's no secret the Uchiha consider him their own."

It made sense, for their world; blood relatives tended to fight more than men brought together under the clan oath. Sakura knew it to be true, thinking of her father's anger.

Or even worse, her mother's gradual shift from disdain to disinterest at discovering her precious child was more yakuza princess than proper young maiden. She thought of Jiraiya, who wasn't her blood but who had shown her more love on a daily basis than either of the parents who birthed her. If Uchiha Fugaku and his predecessor felt the same way about Hatake Kakashi…

Yes, it made sense. But she didn't have to be happy about it.

"Sasuke did have a nice face."

"And a shitty attitude, according to Karin."

Sakura sighed, head against the tinted glass of the car window.

"Ya aren't wrong, Ino-chan," she murmured, "but I'm still going to complain."

"That's what the drinking is for, Sakura-chan," Ino said, flicking her nose and promising a night they'd be recovering from for days.

Of course, Ino delivered. The first few clubs passed by in a blur of sycophants staved off with the careful attention of her bodyguards, men chosen for their relative youth and ability to blend in with the civilian crowds Sakura mingled with on nights downtown. It helped that half of them were in love with her friend, but as she danced and twirled with increasing abandon Sakura found herself wondering if any of them were not-so-secretly in love with her, too.

It had been far too long since she'd found someone worth dating.

This was partially because as the Nidaime's successor she was in a position at once enviable and undesirable. The sole surviving heir to the largest Shikkotsu group - a position cemented now that her father had formally renounced his upbringing - but at the same time unable to officially take over of her own accord.

Brought up with only half a foot in the underworld Sakura resented their often-backwards attitude to women; with Tsunade as her role model she knew very well that she could rule with the iron fist the Senju needed. But even Tsunade had only ruled for a short time after her husband had died before her eldest son had grown up and taken over, and it was only his untimely death that had given her the seat of utmost power once again.

There were even some elders who still clung to the hope that Sakura's father would change his mind.

Try as she might, this attitude wasn't something that would easily change, and Sakura was determined to find a suitor who supported her desire to take charge. A lower-ranked bodyguard who was silly-drunk in love with her would fit the niche nicely, but of course she understood it wasn't to be. She'd marry strategically, aiding Tsunade in avoiding the gang war that was already brewing in the fringes of their territory.

Still, some of the younger Senju clansmen were rather handsome, and as Sakura knocked back the shots she found herself whispering drunkenly to Ino about the relative advantages of asking one of them to accompany her somewhere quieter.

"Sakuraaaa," Ino, as always, held her drink better than anyone, "you know that's a dumb idea."

They twirled about under the lights as Ino waved her hand conspiratorially.

"It's all about making sure they look, and don't touch."

"But Ino-chan, everyone's looking at you!"

Sakura giggled as Ino stopped dancing, holding a cool hand against her hot forehead. She gestured sharply for a glass of water and forced the pink-haired princess to drink it steadily.

"Oh, Forehead," Ino said in her ear, using their childhood nicknames, "I wouldn't be so sure."

It maddened Sakura immensely that her friend wouldn't say any more than that.

Kakashi tugged discreetly at the stiff folds of his hakama trousers, cursing internally at the discomfort Shikkotsu's airs and graces forced on him. Fugaku had advised him to respect the whims of the young Senju heiress - idiotic as he thought they were - and to not repeat the earlier mistake of turning up to a formal meeting in a suit.

Even if Sakura had looked particularly good when she'd changed to match.

Absolutely not, he rebuked himself. Do not follow that train of thought.

The speed of this second meeting had come as a surprise; Kakashi knew Sakura's reputation for scorning potential suitors and had fully expected her to wield some of her not-inconsiderable charm on the Nidaime to stave off any further discussion. He was, it appeared, too big a fish to turn away so soon.

Today they were going to 'tour the gardens' or some other self-important nonsense, and Kakashi could already feel his patience wearing thin as he prepared to pretend to care about the indolent greenery that popped up everywhere in the district.

He scuffed a pebble in annoyance and had to stifle a curse as it lodged firmly in the heavy cord of his traditional geta. There'd be no swift getaways in this gear. And when he approached the front gate to the Senju compound and saw Sakura in a light, summery dress - definitely not a formal kimono - he had to try very, very hard not to let the exasperation bubbling inside show.

"Good afternoon, Kakashi-san," she said with false sweetness. "How well dressed you are. You must be very keen to see our prized peonies."

Kakashi smiled through thin lips. "Good afternoon, Sakura-sama," he replied. "I'm sure they'll be completely fascinating."

He didn't extend a hand; she'd feel his anger at the intentional slight and that was against the rules of the battle. Her dress, coupled with the oversized shades she was wearing, made her look like a university student on a day trip. In contrast, he looked like an overeager, tone-deaf fool.

An old one, to boot.

Watching from the corner of his eye as she took a respectable position to his left, Kakashi again cursed Fugaku for forcing him to bend to her whims. Her white summer dress coupled with plain, flat shoes made her look even younger than her age; which he now knew was just twenty-three years old.

Fuck. When he'd been twenty-three he'd been embroiled in the depths of a bitter rivalry with Obito over the legendary hostess Nohara Rin, a conflict that now seemed so long ago it was barely worth remembering. To find that the Senju heiress was that very age… Kakashi truly cursed Sasuke's ability to weasel his way out of the Sandaime's whims.

"What's your favourite kind of peony?" Sakura asked, interrupting his discontented thoughts.

Kakashi couldn't point out a peony if it was the only flower in the field, so he took a moment to consider his reply, holding back from telling the truth. The ornate pebbled path was playing havoc with his geta-addled balance.

"A tattooed one," he eventually replied.

"Oh?" Sakura's pale pink eyebrows rose above her sunglasses. "It's a common Senju motif, the peony."

"Is that so?" Kakashi murmured, disinterested.

"Indeed," she confirmed, and he caught the sly edge to her tone just in time, "in fact, I have a peony tattoo myself - maybe I'll show you, sometime."

Against his will, Kakashi found his eyes sliding to the young woman as she walked beside him, hands behind her back. Her dress bared her arms and most of her shoulders, both of which looked tattoo-free; that meant any ink she did have would be located in less… neutral places.

"Would you like that?"

"Hmm," he said, noncommittally, and contained a smirk at her audible tut.

He wasn't going to be caught out; the Uchiha had gathered quite a dossier on Sakura, learning that she liked to try and trick her suitors into saying or doing something inappropriate. And in previous examples, she'd used it as a way to break off the engagement, without risk of insult on the Senju end.

Kakashi grudgingly admitted that it wasn't a bad plan. The problem was that unlike his predecessors, he didn't actually want the position a marriage with her would grant. This disinterest made him cautious; too bad for Sakura that the only way Kakashi was going to sabotage this little arrangement was if the Uchiha bosses told him to.

Otherwise, breaking the engagement would be a Senju offence alone.

Her plan thwarted, Sakura spent the rest of their meeting in almost frigid silence. Kakashi felt triumphant when it was broken only by his own lukewarm thanks for showing him a bountiful harvest of flowers.

Somehow, he doubted there would be a third appointment.

"Thanks for accompanying me on such short notice, Kakashi-san."

Sakura was certain the yakuza was irritated, but he smoothed the expression away before she could get a closer look, bowing from the waist. She gave him a broad, toothy grin.

"Of course," he said with a smile that was nearly convincing. "I couldn't refuse the request."

She wasn't stupid; the Uchiha Sandaime had made the request, and that was who Kakashi couldn't say no to. If Sakura herself had demanded he drop everything and rush to Konoha's downtown shopping district, then she knew he'd have come up with a particularly creative way to tell her to fuck off.

Their first meeting had been funny. The second had been frustrating. Sakura wasn't sure how the third one would go, only that both Tsunade and Ino agreed that she should make the trip to his neck of the woods. To see how Kakashi handled it, they said.

Rather badly, Sakura thought. Maybe she'd interrupted something.

This was likely to be their final meeting; Hatake Kakashi had been wise to her usual tricks, and she'd spent the last week with Ino strategising about how to make the gruff yakuza admit defeat. Her master plan involved being saccharine sweet, because playing the brat hadn't worked, and she rather thought he'd hate a cutesy act more.

"Did you have anything in particular you needed to do?" Kakashi asked, breaking her reverie. "If you want to shop, I'm sure we can find a VIP store, and you can do it in comfort."

It was raining lightly in Konoha. She'd left Shikkotsu earlier that day in full sunshine, dressing to match. Sakura didn't make the trip east often; less so now that she had to do it under guard. She'd forgotten the weather could be more changeable in this part of the country.

"Shop?" Sakura repeated bluntly. "Why do you think I want to shop?"

Her grandmother had bet that Sakura would crack in twenty minutes. Ino had been gracious enough to say an hour. From her driver's muffled wheezing, he had accurately bet that she wouldn't last five minutes playing the sweetling. In fact, she'd barely made it out of the car.

Kakashi looked around, swivelling his big black umbrella. She watched him do it, enjoying the way his trouser legs were slightly wet from the rain, sticking to his ankles. If he had had those tailor-made, then they wouldn't have draped so poorly.

"Because… you requested I meet you in the shopping district?" he said, blatantly nonplussed.

Sakura laughed.

"I don't buy off-rack," she said in lieu of explanation, holding out her hand for him to take.

She didn't miss the way he laid it across his arm as though she was poisonous. Nevertheless, he held the umbrella angled so that she didn't get wet. He sauntered at a pace that was easy to keep up with, too. It was clear that Kakashi was used to accompanying women, a thought that occupied her as they walked down the rainy Konoha street.

The cutesy act was out. And since she didn't particularly enjoy being bratty all that was left was to be herself, an option which had driven off several suitors in the past.

"Do you have a destination in mind?" Kakashi tried again.

No, Sakura cursed silently. Out loud, she said:

"Got any good casinos out here?"

From the way he missed a step that was not what Kakashi expected her to say. It was early in the day, for one thing. For another, Sakura was careful to keep her baccarat antics quiet, so it's unlikely that even the Uchiha intelligencers knew of her hobby. People tended to assume she didn't enjoy life in the underworld, largely because they also assumed she'd been forced into accepting her heritage.

"You like gambling?"

Giving Kakashi a serene look from under her lashes - the one that made Jiraiya-jii-chan let her win at cards - Sakura simply shrugged.

Kakashi said nothing in response. But he did steer them away from the shopping street, walking with more purpose towards an area that Sakura recognised as the seedier side of town. Civilians began crossing the road to avoid them, some with respectful bows, and she knew they'd crossed into Uchiha territory proper. Kakashi was clearly recognised.

Her bodyguards probably didn't help.

And in any case her date was every inch the underground boss: his suit (even if it didn't fit) was expensive, his shoes pristine, and his demeanour dangerous. There was a faint aroma of cigarette smoke around him this time, and she wondered again if he'd been caught by surprise with her request. Where Sakura could easily blend into the outsider crowd, Kakashi was a yakuza through and through.

"I like cards," she offered eventually. "All yakuza like playing cards."

"True enough."

"So, has this city got any good spots, or are my pockets full until I get home?"

For the first time during their acquaintance, Kakashi's smile looked genuine.

"Wanna make a bet?" he asked.

It was the first time he'd spoken casually. Sakura tightened her fingers on his arm, surprised at how much younger it made him sound. They'd drawn to a stop outside a smart-looking izakaya, its indigo blue curtain proclaiming its status as purveyors of fine smoked seafood. No doubt it was a front; the Senju were fond of using food shops too, because they doubled up as good meeting places when necessary.

"I ain't placing a bet with you in an Uchiha den," she said without rancour. Did he think she was born yesterday?

"Scared?"

"Sensible," Sakura snorted. "You forget I learned from the best."

Tsunade's reputation was well-earned in more ways than one.

"I could never forget that," said Kakashi.

When she turned to look up at him, expecting a smirk, she saw that his face was serious. Assessing. As if he was changing his no-doubt terrible impression of her. As if he'd say yes to a fourth meeting, and a fifth.

Following Kakashi into the interior of the dim but well-kept gambling den, Sakura considered whether she was about to end up engaged to a man several years her senior, with trousers that were begging to be retailored.

She took another look, only to discover that while they were too long in the leg, his trousers were certainly good at enhancing some of his other assets. Namely his ass, which was as criminal as the rest of him.

Well, Sakura thought, shit.

It felt like she was about to discover that the Uchiha's loyal dog did, in fact, bite back.

Tsunade sat back with a sigh, enjoying the fragrant burn of the sake as it travelled down her throat. Jiraiya had surrendered several bottles of his gifted Myoboku sake to her - on pain of death, he'd grumbled - and it was a pleasant accompaniment to her after-dinner horse racing.

To her left sat Shizune, her brilliant and beautiful daughter-in-law, whom many of the clansmen referred to as the second Slugger Princess. Shizune was her closest companion after her husband's untimely death, especially since Tsunade's own husband travelled often. They spent many evenings like this, two women relaxing after a hard day at the top of a male-dominated world.

"Shizune," Tsunade began, idly watching the horses as they lined up on screen, "Sakura's quite late home."

The brown-haired yakuza pulled her phone from her yukata, checking her notifications. Tsunade didn't need to look to see that the lockscreen would proudly bear a picture of the deceased Senju Sandaime.

"I haven't heard anything, mother," Shizune replied. "And no news is good news, when it comes to dating."

Tsunade snorted, taking another long sip of sake.

"I would hardly call what's going on here dating."

It was hard not to feel bad. She'd had a love match with Dan, and a love-hate match with Jiraiya. Sakura's father had run away because of lust, and her other son had been happy with Shizune. To force Sakura into a dry arrangement for the benefit of the clan left a sour feeling in her stomach. Even if her granddaughter had assured her, over and over, that she was fine with it.

"Still," Shizune said, "someone would have gotten in touch, if things had gone south."

The double meaning was not lost on Tsunade. The looming clan war had meant she'd sent a ludicrous amount of men with Sakura, almost enough that they were a liability through their overbearing presence. But she wouldn't lose another family member to this lifestyle. She couldn't.

"I just hope Sakura hasn't cursed him out over his outfit," Tsunade muttered, only half joking.

"Surely not."

Shizune didn't sound convinced.

The horse racing began, six riders on Shikkotsu's best beasts racing across the pristine turf. On screen it looked effortless, as though they were simply gliding along in an unchanging gait. Live racing was far better. However, the Senju had recently been accused of match fixing, so a low profile at these events was necessary for the foreseeable future.

The match fixing accusations were accurate, but the fewer people knew it, the better.

Several races had passed when a flurry of activity in the compound announced Sakura's return. From the inner chambers the two women heard the lined-up greetings of the men for their heiress as well as Ino's far less formal welcome home, girl. Trying not to look as though she'd been eagerly waiting for her granddaughter's return, Tsunade opened another sake bottle, affecting an air of distraction.

"Obaa-sama!" Sakura called from the doorway, Ino trailing behind.

Sakura's hair was slightly wet, curling at the ends. Tsunade thought she was flushed, though whether it was from weather or alcohol was hard to say.

"Sakura-chan," she greeted. "Come in, come in. The 400 metre is about to start."

Just like any other day. Shizune handed the pink-haired princess a cup of sake, catching her mother-in-law's gaze. Tsunade winked where Sakura couldn't see. Beside her, Ino looked fit to burst with curiosity.

"Who's our guy?" Sakura asked.

"Number four," Tsunade said, pointing with her sake cup to the jockey in question. "Though I've also put a bet on number six to keep things interesting."

Sakura whistled appreciatively, settling down to watch. Outside, her bodyguards bowed and moved to their other duties. Sakura stifled a yawn, as though she'd had an entirely uneventful outing. She'd missed dinner, but presently a senior clansman brought them a plate of snacks, ruffling her pink hair before he left.

Tsunade was almost lulled into a sense of normality when Sakura turned to face her, wiping senbei crumbs from her face.

"Baa-chan."

"Hmm?"

"We should probably start thinking about my wedding kimono."

There was a chorus of surprise as Ino, Shizune and Tsunade all spoke at once, the former two quieting down only when the Nidaime roared "WHAT?" in a voice so loud her bodyguard came running. Through it all Sakura sat as composed as though she'd been talking about the weather.

"Pour me a damn drink," Tsunade commanded, taking a deep draught when Shizune complied. "Now, what the hell are you talking about?"

Sakura picked at her manicured nails, looking for all the world as though she hadn't just said something shocking. Whatever had happened on their third outing had clearly not been within her plan. And unless Tsunade was mistaken, she didn't think her granddaughter was particularly disappointed.

"I was myself," Sakura said matter-of-factly. "I think he liked it."

It had been the same with Dan. When a much-younger Tsunade had tried to scare him off with her larger-than-life personality, the junior clansman had simply chased her harder. When she'd thrown a fist in his direction, her first husband had offered to help work on her form. When the same had happened with Jiraiya, the old fool had told her he'd take anything she threw at him, including herself. Some yakuza liked their women strong, a trait the Nidaime approved of.

Hatake Kakashi was, perhaps, made in that mould.

"Well then," Tsunade said faintly. Not even Myoboku sake could take the edge off of the realisation that she was old enough to have a married grandchild. Beside her, Shizune looked similarly overcome.

"Let's get this engagement planned, shall we?"

AN: hope you enjoyed! Let me know if you did 3