This was a story I have had sitting in my computer since 2017... While finally I thought I might as well upload it and finish writing it among other stories I have locked away. Of course my other story Sasuhina centered Forever will be updated soon as well but in the mean time please enjoy the Naruto characters placed in the real world. Honestly it's real nice to take a break from writing Sasuke and in universe to explore other characters. I found out that I like writing Ino more than I thought I did, her perspective is really refreshing and just overall fun to explore and so unlike the more introverted perspectives I'm used to with characters like Sasuke or even Hinata.

Overall, I'm pretty happy to finally have this first chapter out as it's literally been years since I first wrote it.

Disclaimer: I don't own Naruto and also this is inspired by the romcom of the same name though when I say inspired I do mean loosely, none of the plot points will be the same except for the premise.

Chapter 1

Ino Yamanaka and Shikamaru Nara were always inseparable. Their story started the minute they were born one day apart from each other. Wherever one went, the other followed. And it been like that for a long time.

It came as no surprise to anyone when they had finally gotten together, their friends secretly rooting them on, especially their best-friend Chouji Akimichi who swore they were already dating anyway. It did however, come as a shock when they drifted apart a couple of years later. It was after graduating from college. Shikamaru moved away to handle some business with his father in the Beach capital city of Suna, and Ino stayed behind so she could help out her family's flower shop Yamanaka Bloom in Konoha whenever she was needed.

They had still kept in touch via video messaging, emails, and texting, and the two hung out with Chouji whenever Shikamaru and his family happened to be in town, but it was obvious that something had changed for them.

At least that's how Ino interpreted it. Shikamaru however didn't think the same way, he knew exactly why they didn't work out, but just didn't feel the need to hash it out.

So, she was genuinely surprised when he hit her up about hanging out later that evening at their favourite bar spot "Drunken Stupor" … sans Chouji.

Glancing outside her purple curtained window, Ino examined the fall leaf-covered ground and racked her brain for possible outfit ideas. When she was satisfied with the visual that entered her mind, she entered her walk-in closet and zoned in on the pieces. A warm long knitted green cardigan with a white fitted tee and some dark wash jeans. For shoes she would go with a simple white heel, nothing too flashy or tall, it was just a simple meet-up. Turning towards the bag section of her closet, she settled on a cute tan, brown purse with a little gold heart as the closing button.

Examining herself in her vanity mirror, she applied her makeup to look as if she wasn't really wearing any, but definitely was. Brushing her long platinum blonde hair, she tied it up and opened her chest of pins for something to hold back her long side bangs, she settled on the little turquoise firefly Shikamaru had bought her a while back when they were dating. He had bought it saying it reminded him of her eyes, a trait he admitted to falling for when he had confessed his feelings. She hoped that when he saw her wearing it, he would be reminded of when he gave it to her, and in turn how they felt back then.

Giving herself a once over in the longer, admittedly too big, full-body mirror she had propped up in the corner of her room, Ino approved of her casual but dressy appearance and grabbed her keys, heading into the crisp winter air outside of her apartment.

Admittedly she was very nervous. She had heard from her best-friend Sakura Haruno that Shikamaru was moving back to Konoha sometime this month, something which said girl had heard from a conversation her boyfriend and resident asshole, Sasuke Uchiha was having with Naruto Uzumaki while on a double date with him and his girlfriend, Hinata Hyūga.

The platinum blonde hoped that with him permanently being back this time around that they could give each other another try.

She never really got over him if she was being honest with herself.

Tapping her fingers absentmindedly on the wheel, Ino silently drove to her destination as she let the catchy pop music blasting through her speakers fill her brain with mush instead of her own nervous thoughts.

Upon arrival, she looked up at the small red brick building through her window. The neon pink letters of the bar sign that spelt out "Drunken Stupor" were all aglow except for the letter "t", so it ended up looking like "Drunken Supor" instead. She shook her head, she remembered specifically telling the owner, also known as Sakura's boyfriend's brother, about that very same problem a few weeks back, but it seemed he didn't get around to doing anything about it yet.

Flipping the car mirror above her over, Ino applied another coat of her favourite pink lip-gloss until she was certain she looked absolutely perfect, and then entered the bar. The warm cozy feeling of the place wrapped around her body as the swinging bell above the door announced her arrival.

The bar's aesthetic consisted of cherry stained wood everything – from counters to chairs and tables, accentuated by the red neon glow of the lights. Some navy sofas were positioned directly in front of a warm and sizeable fireplace, and pictures of abstract art hung inside large sleek black frames. The air held the distinctive smell of freshly cut cedar chips and hard liquor mixed together, a smell that for Ino, took a little getting used to the first time around.

Standing at the door, Ino scanned the room looking for her best friend with no luck. Biting her lip, the blonde stood still unsure if she should go back and wait in her car, until she spotted the familiar face of Sai- "no last name"- working the counter and decided against it.

He had on his standard black fitted tee along with a pair of loose ash grey jeans, it was such a simple outfit really, but he still managed to look like a model in it. Walking towards him she sat down as he shot her one of his ever-present awkward smiles. He served the customer ahead of her first before making his way over where she positioned herself.

Examining her outfit, he raised a dark eyebrow at her countenance, Ino was always dolled up but it was usually in a more effortless way. This particular look she donned however looked much more calculated than the one's before.

"Waiting on someone special?" He asked her, nodding his head in her direction.

Coyly smiling, Ino leaned forward on the bar counter, "Why, are you jealous?"

"Of course not. Nothing to be jealous over Beautiful. Besides," said Sai, pointing his hands towards himself, "I don't get caught up in emotions."

"I'll have you know that I am a catch." Ino glared, the sweet nickname having lost its effect on her long ago, "And maybe that's because you're incapable of feeling them, or at least that's what Sakura says."

"Sakura's just mad I called her ugly all those years ago."

"What do you mean all those years ago, you still do." Ino reminded him. Sai was definitely a looker but sometimes he left her wondering if he was alright in the brain.

Sai blinked a few times, and then let out a low hum, "I guess I do." Reaching for the empty glasses underneath the counter he put one in front of Ino. "Do you want what you usually have? Or are you watching your weight again?"

Pursing her lips Ino felt her face twitch at Sai's rudeness. She contemplated ripping him a new one, but then reminded herself of what Naruto told her, in the social sense Sai …was a dumb ass. "Just surprise me, asshole." She muttered, trying to keep calm.

"Alright." He said, a quaint smile playing at his lips.

Tapping her fingers rhythmically across the wooden bar surface, she watched as Sai expertly prepared the mystery drink before her with such precision. He made it look like an art form, perfectly shifting the cocktail mixer between each palm of his hands in balance until he was satisfied. Filling her empty glass with plenty ice, he poured the drink to the brim and waited for her to take a sip.

Peering up at him through her lashes, she swirled her finger on the top of the glass and then took a sip letting the alcohol hit the back of her throat. The taste was sweet with a hint of spice. Running her tongue across the top of her mouth she tried to pinpoint the exact ingredients but the only one she could identify was rum.

Sai raised his brow expectantly waiting for her verdict, "How is it?"

"It's good," said Ino, still trying to name the flavours in it, "What's in it?"

"It's my special concoction named Root. I'm not going to tell you what's in it, though I can assure you it meets your dieting needs." He said with an empty smile.

"You know what, fuck you, you're such a-" She fumed, only pausing when her attention was drawn away by the ringing sound of the door opening.

Suddenly she reached up to straighten out her hair, following her line of vision Sai could see Shikamaru Nara standing at the front of the bar.

"Doesn't Shikamaru live in Suna?" He asked Ino, but she seemed to not hear him as she got up quickly to run over to him.

Grinning wide, Ino gripped Shikamaru in a bear hug as he awkwardly reciprocated, lazily patting her back.

"Alright, alright Ino, let me breathe." Shikamaru said, ripping her away from him. Getting a good look at her he noticed the pin in her hair and shot her a lazy grin, "Haven't seen that one in years. The pin I mean."

"Well you've been gone a while." Ino mumbled, running her fingers through her hair in embarrassment.

"Didn't think you'd still have it."

"Of course, I would!" she huffed upset he would even think such a thing. Shortly after she shyly added, "You gave it to me…"

Letting out a low chuckle Shikamaru shook his head at his best-friend. Pulling her closer to him he lazily hung a hand over her shoulder oblivious to the furious shade of red that made its way to Ino's cheeks. Walking towards an empty spot he let her go and took a seat, reaching for the random menu in the middle of the table.

"I haven't had a drink in forever," He mused as his eyes scanned the different types of drinks there were to order.

"What, is the stuff in Suna no good?" Ino joked.

"Well that, amongst other troublesome reasons…" Clearing his throat he moved to change the subject before Ino thought better to question him over it much like her nosy self tended to do, "What do you recommend?"

"Uh, Sai made me some secret drink not too long ago, you should ask him for that. What did he call it…uh...Root?"

Raising a brow at the sentence Shikamaru looked over towards the bar where a pale as the dead man, with neck length dark hair was preparing a drink for a customer. He seemed familiar, but the articulate man just chalked it up to him resembling a friend of his. "Sai?"

"For a genius you're really slow," Ino laughed. She reached playfully across the table to shove him, "He's Naruto's friend from college, we all met him at that bonfire two years ago remember? Well anyways, Naruto being so damn persuasive managed to convince Sasuke to get his brother to give Sai a job here a few months ago. Although come to think of it, you haven't visited Konoha in a while, so you probably never saw him around much either way."

Processing the information Shikamaru racked through his brain as he pulled up the memory. Ah, it was that Sai.

"Ah, wait I think I do remember. The emotionally constipated one, right? Naruto really has a knack for befriending those types of people. But damn it's really been that long, huh?" said Shikamaru, softly shaking his head.

"Yeah," Said Ino. Casting her eyes downwards she averted her gaze away from his, "But it felt longer to me."

He didn't answer, choosing instead to lean back in his chair and silently exhale. He hadn't seen Ino since last September, approximately six months since he last visited Konoha. He didn't know where exactly they stood anymore if he thought about it.

"How's work? Your parents, are they doing well?" He asked, leaning forward, and propping his head atop his arm.

"They're good, everything's been…good." She winced at the last bit. Why the hell was she being so awkward? It wasn't like they were strangers or anything, well, not entirely that is. Motioning her chin towards him she shot his question right back at him, "How about you? How are things? You look like a caveman by the way." She laughed, poking fun at the five-o'clock shadow that her best friend now donned.

"Actually, that's what I wanted to talk to you about..." He trailed off, turning his attention towards the door as if expecting something.

About to ask him if something was wrong, the bell of the opening door drew away her focus as a woman with sandy blond hair hastily pulled into two loose pigtails, entered the bar. She was wearing a light purple dress shirt, a maroon pencil skirt and a pair of black pumps with a cute small black purse hanging off her shoulder. If Ino had to guess the woman had just got off from work and was craving something to get the past few hours off her mind. To the platinum blonde's surprise however, the woman's eyes lit up as she scanned the room and landed on her and Shikamaru's table.

Raising her hand in a semi wave, she sped up her steps and made her way over to them. Pulling up a chair between Shikamaru and Ino- who both sat at either ends of the table- she sat down with a sigh, as she adjusted her bag to her lap.

Before Ino could ask the girl what exactly it was she thought she was doing, Shikamaru turned towards the woman with a smile she recognized as one he used to give her- though she couldn't exactly remember when he had used it.

"Get lost?" He playfully asked, scooting his chair closer towards the sandy blonde as she turned away in a scowl.

"It's not my fault your city's roads are so freaking confusing," She scoffed, crossing her arms childishly. As if remembering her place, her expression quickly changed as she shifted her attention to the other blonde to the right of her. "Oh, I'm so sorry. You must think I'm extremely rude right now. Nice to meet you Ino! Shikamaru's told me so much about you."

Extending her hand, the woman boyishly grinned at Ino, as the blonde looked down at her hand in confusion before taking it and shaking it.

"Nice to meet you, Uhm….?"

"Temari," Shikamaru interjected looking between the two with a small smile. "You forgot to tell her your name. Troublesome."

Nervously chuckling Temari retracted her hand to clumsily rub the back of her neck, "Ah right! Sorry…I'm kind of nervous."

"Temari." Ino repeated, feeling the name on her lips. Looking between the two she noticed how Shikamaru unconsciously turned his body towards the sandy blonde, smiling at her in such a gentle way she couldn't bare to see.

"Don't be nervous." Said Shikamaru, reaching for Temari's hand underneath the table and placing their intertwined hands on the top of the wooden surface, where Ino could see.

Glancing at their hands, the platinum blonde could feel her heart drop as she registered the diamond and gold band that sat on Temari's ring finger. Looking up towards Shikamaru, she could see that he was gauging her reaction. Keeping her countenance neutral, she tried not to reveal the fact that her thoughts were swirling madly.

She felt like she was going to be sick.

Forcing a smile, she turned towards Temari as she tried to keep herself together, "Your ring, it's very pretty."

"Thank you," the woman grinned looking down at her hand with pride, "I'm not really a fan of flashy stuff, but he insisted on me keeping it when I tried to get him to switch it out for something more subtle. I've learned to love it though."

"You're getting married," Ino breathed, the words leaving a bitter aftertaste on her tongue.

"I wanted to tell you in person," Shikamaru explained, looking at her with a sharp gaze, "I know how much you love to talk, didn't want it spreading around town until we were ready. That would've been a real drag. I'm sorry."

Shaking her head Ino could feel her face beginning to hurt from the forced smile she kept in place, "Don't worry about it," She laughed, "I completely understand."

"Thanks, Ino."

"I'm really happy for you Shikamaru," she lied, still smiling that damned fake smile. She tried to calm her thoughts inside, as she looked at the two with as much fake happiness as she could muster. In reality, she just wanted to run away and never look back, maybe crawl in a hole somewhere. "How long?"

"Three months." Temari said, grinning at Shikamaru with adoration.

Running his thumb across Temari's fingers, Shikamaru turned towards the sandy blonde with the same expression Ino couldn't quite place earlier but had finally begun to register.

That look. He used to give her that same look when they were dating.

Ino wondered if her best friend could feel her heart break, but by the way he pulled Temari even closer towards him, she guessed he hadn't.

Despite his generally lax nature, and though he didn't seem like the type, Shikamaru was a very affectionate person, even in public. Ino remembered the moments when he would nonchalantly do something like that to her in front of the rest of their friends and cause her to become a fumbling mess.

Noticing Ino's unusual quietness, Shikamaru turned towards her with a questioning glance. She had been acting quite strange since Temari's arrival and had begun to withdraw within herself. He knew she must've been completely taken back by the news and was trying to hide it, but he wasn't so easy to fool, though he thought it would be best not to directly question her on it.

Tapping the table with his free hand, he watched as Ino blinked and then looked at him, "You there Ino?"

Coming to, she shook her head and smiled. She knew if she didn't make it believable enough he would completely see right through her act, and that would be completely mortifying. "Sorry, little bit tired from work. Had to take an early shift today then help out at the shop remember?"

Accepting that as a plausible answer Shikamaru nodded, "Yeah I remember. You must be tired."

"Very." She said. Though it was for a completely different reason than the one she gave him. Looking towards the bar she could see Sai curiously staring at her from where he stood.

Catching her gaze, Sai tensely smiled at Ino and motioned if she wanted to drink to which she nodded. At her confirmation, he made his way over to their table against normal bar protocol, mostly to say hi.

He had very rarely seen Shikamaru while he stayed in Suna, but from their small interactions and from seeing his dynamic with Naruto, Sai thought that he seemed to be a friend worth having. Besides, Naruto always encouraged him to get to know some of the other people within their circle. Said it would help him with his lack of social skills.

Clearing his throat to announce his presence, Sai noticed the weird atmosphere that surrounded one person entirely. Ino, who had been much happier when he'd first seen her that evening, had taken to donning a plastic smile. He himself only knew it was true because it looked similar to the smile he always gave everyone else, meaningless, and virtually empty behind the eyes. Shifting his attention to the other woman at the table, Sai noticed that not only was her hand firmly in the grip of Shikamaru Nara, but that one of her fingers also sported a nice piece of jewellery on it.

Looking between the three, it didn't take long for him to piece together the situation based on the information available to him. From what he observed when watching Ino, and just from being around to witness conversations Sakura had with her best friend, Ino loved Shikamaru, and now it seemed that the man she was in love with was getting married to someone else.

Though he wasn't one to feel emotional for just about…well anything, Sai did feel really bad for Ino. She was, for the most part, always nice to him despite his lack of social skills and never treated him like he was weird or anything for it. Glancing at her with a blank expression he waited until they all looked up at him before speaking.

"Pardon me, I know bartenders don't wait on tables, but I just wanted to come over and give my greetings to Shikamaru."

"Oh hey, Sai," Shikamaru said, scratching the small bit of scruff that lay on his chin. "To be honest I kind of didn't recognize you earlier. We never really talked much did we?"

"It's ok, I know you live in Suna and we haven't really spoken much. Maybe one day we can hang out with Naruto, that is if you manage to get out of bed." Before Shikamaru could ask him what that was supposed to mean, Sai nodded his chin towards the other blonde woman at the table and thinly smiled, "Not to overstep but I noticed she has a ring on her finger. Is she…?'

"Right," the man lazily drawled. Suddenly his eyes perked up as he received a nudge from the woman next to him. Chuckling absentmindedly, he strengthened the grip he had on her hand as a relaxed smile found its way to his lips, "This is my fiancée Temari. I was going to let the whole gang know a little later this week but since you're already here I might as well tell you before Ino's big mouth does."

"I see..." He stayed silent trying to formulate his words, Naruto had told him that one key to a great conversation was noting something about the individual to show attentiveness. Clasping his hands together Sai looked between the trio a second time before noting, "I see you like blondes."

Coughing at the tactlessness of the sentence, Shikamaru narrowed his eyes at the bartender, "What is your problem?" he scowled.

Looking up in thought Sai shrugged his shoulders shortly after, "Nothing that I'm aware of."

Inhaling rather dramatically, Ino loudly smacked her lips together and opened her mouth wordlessly. Sai stood still along with everyone as they waited for her to speak, only to grow confused when the seconds ticked by and she still hadn't said anything.

"Ino?" Sai voiced, wondering why she stood frozen in place.

Blinking rapidly, Ino still didn't say anything and instead abruptly rose from the table, hands slamming on the surface. Flinching at the rather strange reaction, Sai was taken by surprise when the platinum blonde rudely pushed him out of the way to rush into the bathroom.