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Summary:

When Felicity's parents announce that they're hiring someone to be her personal bodyguard, what she hears is that she's going to be stuck with a 24/7 babysitter... something she is so not on board with.

When Oliver takes up the offer to work for the Smoak family he thinks it's just another job, but he has no idea what he's about to get himself into.

Protecting the "tech empire heiress" is the easy part, matters of the heart are where things get a bit more complicated.

Notes:

Hey guys! Thank you in advance for checking out my latest AU, I've been having a lot of fun writing this one and I hope that you will enjoy it! For this AU I really wanted to play around with a world where Felicity's dad was around and how that might affect her life. So just as a heads up, I've done a bit of changing things around with both Oliver and Felicity's backstories, but those changes get well explained throughout the story I promise.

I want to thank my beta Aubrey, who makes sure that my chapters are readable before I post them and provides very important encouragement; Sara (gothsmoak.tumblr.com), who designed the amazing artwork; and also everyone on twitter who provides suggestions when I tweet out really random requests for help with stuff in this story :)

Without further ado, enjoy the story!

(See the end of the work for more notes.)

Chapter 1: Chapter 1

Chapter Text

APRIL

Starling City Rockets Set to Open their Season at Home this Weekend

City Hall Votes Unanimously in Favor of New School District Zoning

Tech Empire Heiress Felicity Smoak Spotted Exiting Table Salt with Mysterious Suitor

“I wonder if Curtis is aware that, not only is he into girls, but he’s also my suitor,” she muttered as she finished her swipe through the news stories that had popped up that morning on her tablet, making a mental note to send a little virtual “present” to the author of said article. “Suitor. What am I? The Duchess of Cambridge?”

“What honey?” her mom asked from across the table where she was flipping through a magazine while she ate breakfast. Donna Smoak was living proof that you can take the girl out of Vegas, but you can’t take the Vegas out of the girl. While she used to be a little bit embarrassed by the way her mom dressed and did her hair and makeup, now she appreciated the way that she hadn’t let the backhanded compliments, tossed out by women whose social circles she had entered when their family had started to move up in the world, turn her into someone she wasn’t. Her mom was classy and smart and well respected, and yes, she also happened to rock Hervé Léger bodycon dresses “at her age.”

“Nothing,” she waved her hand dismissively before reaching across the table for a muffin. “Just catching up on the exciting details of my life. I’m so relieved people are getting paid to keep me up to date.”

Her mom’s eyebrows furrowed, “Were people following you at dinner last night?”

Her mom had been getting that nervous look a lot lately and she really thought that it was rather unnecessary in this instance. For as long as she could remember there had been people taking her picture, wanting to get a quote they could splash across a headline, or making up ridiculous stories about her and her daily activities. It was rather unfortunate for the gossip loving people of Starling that their resident teenage billionaire was incredibly boring and had yet to do anything TMZ worthy scandalous with all her money and privilege, but the journalists truly did their best with what she gave them. Perhaps some of them should switch to writing fictional novels, they certainly possessed the creativity for it.

“Just the usual photographers who think my boring life is worth capturing,” she replied nonchalantly before taking a bite of her muffin. Blueberry, freshly baked. Caroline must be back from visiting her sister. She would have to remember to pop into the kitchen after work and ask if she had stayed caught up on Quantico while she was gone. And also if she would pretty please make her amazing lasagna for dinner some night this week. “You would have thought that people would’ve lost interest in me by now.”

“You’re rich and pretty. Haven’t you watched enough television? They’ll never lose interest.” Her dad entered the room, a teasing tone to his voice and she grinned as he came over and kissed the top of her head.

“Things should calm down in the fall though, right? I mean, in New York, you could walk down the street and bump into a cast member from Hamilton, so surely no one is going to care about me. And at MIT, I’m just going to be another student...” Right?

“Who on the weekends helps run a fortune 500 company that bears her last name,” her dad added pointedly as he sat down next to her mom and started to eat the breakfast that had been set in front of him.

When her mom had managed to convince her father to give up the line of work that had gotten him close to federal prison on more than one occasion, he had channeled his skills into a much more legal venture with his business savvy brother-in-law. That’s how Kuttler & Smoak had gotten its start thirteen years ago. Now they were the country’s leading software and application development company and also provided their cyber security services to many important companies and agencies, as well as celebrity clients.

From the day she’d stolen parts from her father’s study to build her own computer at the tender age of seven, her parents had known that she was going to fit right in to the family business. All throughout high school she had been shadowing her dad at the Starling headquarters and, come the fall, she would be attending MIT while taking on more responsibilities at the new east coast office in New York with her Uncle Daniel.

She sighed, “Good point.”

“This all actually leads into something your father and I have been meaning to discuss with you,” her mom began tentatively.

Her hand that was reaching for a second muffin, froze and she flicked her eyes back and forth between her parents warily. Her mom was being all business and serious, which was uncharacteristic of her and a little unnerving. This was probably not just going to be a chat about the little (not so little) charge she had put on the credit card last night when she was doing some online shopping at Nordstrom and whether or not she had bought anything she was going to want to borrow.

“We think it’s time that you have your own bodyguard.”

She blinked, “A bodyguard?”

It was hard enough for her to try to blend in and get people to treat her like a normal person when there was a high rise building in the middle of the city with her last name on it, having a bodyguard was certainly not going to help. It wasn’t like she was ungrateful for the privileges she had because of her family’s success, and she loved being a part of it with her role at the company, she just wished that all of that didn’t have to come with her own personal shadow in the form of some intimidating looking guy in a suit.

“Yes,” her mom nodded. “As you’ve gotten older, we’ve let you have a lot of freedom and independence because you’ve proven yourself to be mature and trustworthy, —”

“And yet you’re sticking me with a babysitter,” she interjected, annoyance bubbling up inside of her.

“Which means you’re no longer around us all the time and accompanied by the family security detail,” her mom continued, ignoring her interruption. “And for a while we let that slide, but with the privileges you have because of our wealth, there also comes necessary precautions. Especially with you getting ready to move in the fall, we have valid reasons for wanting someone to look out for you.”  

While she got the feeling that this bodyguard thing wasn’t up to discussion, she possessed every bit of her mother’s stubbornness and she wasn’t going down without a fight.

Her phone buzzed and she saw the text notification pop up on the screen.

SARA: Pulling in now

“What about what I want?” she asked, standing up and slinging her bag over her shoulder. “Because I don’t want a bodyguard. I’d like to avoid giving off the impression that I think I’m a Kardashian, so that people will actually want to be my friend.”

Throwing a tantrum was not going to help anything in this situation, especially since she had just been applauded for her maturity, but she had to admit it kind of felt good to storm out of the dining room dramatically.

“I’m riding to school with Sara,” she yelled as she walked down the hallway, not looking back at her parents.

She ducked into the passenger seat of Sara’s car and her friend turned to her with an amused expression on her face, “What’s got you all grumpy this morning? Have things turned sour with your new suitor? You should know that I laughed for a solid 5 minutes when I saw that.”

Rolling her eyes, she buckled her seatbelt, “I was out to dinner for a birthday party with a bunch of co-workers and Curtis just happened to be the one person who left at the same time as me. The even more laughable part is that he was telling me about his new boyfriend when they took that picture.”

Sara snorted, “You gotta applaud their dedication to reporting the truth. So what’s the real reason for that murderous look that was on your face when you walked out here?”

“My parents just broke the news to me that they’re setting me up with my own personal 24/7 babysitter,” she explained while Sara pulled out of the driveway.

“What?”

She sighed, “A bodyguard.”

“Oh. Why? Have you received threats or something?”

She hadn’t even considered that. There were always the general kidnapper types that were looking to make a good profit off of a billionaire daughter’s ransom, add to that the people her Dad had pissed off when he was a wanted criminal, and it was certainly plausible that there had been threats her parents had declined to tell her about. At the same time though, she had spent tons of time without her family’s security detail tailing her and nothing had happened to her. She didn’t want to start feeling paranoid now, and having a bodyguard seemed like it would just make her stand out even more as someone worth kidnapping.

“No,” she assured Sara. “They’re just being paranoid; so don’t you start worrying too.”   

“Oh I’m not worried; I know 3 different ways to kill people with my pinky finger. If someone wants to get to you, they’re going to have to get through me first. Your parents can just hire me as your bodyguard,” Sara teased.

The slightly scary part was that she probably wasn’t joking at all about the killing people with her pinky finger thing. Sara was into mixed martial arts and gymnastics and there was a 90% chance her superlative in the yearbook this year was going to be, “Most Likely to Win American Ninja Warrior.”

They were definitely an unlikely pair, but she couldn’t remember a time that they weren’t best friends.

She fished around in her bag for her lipstick, “Be careful what you offer. I’m pretty sure you don’t actually want to give up your Hollywood dreams just to follow me around all the time.”  

She had tried not to think about the fact that after graduation they were going to be going their separate ways, her to the East Coast and Sara to Southern California to work as a stunt double, but the closer that day got, the more she couldn’t avoid it being on her mind. It was probably the biggest thing keeping her from being 100% excited about next fall…. closely tied now with the recent addition of this whole potential bodyguard situation.

“Plus, I think your parents want someone who will keep you out of trouble, and we both know that’s not really my specialty,” Sara replied, glancing over and tossing her a wink.  

When they arrived at school, they parted ways to go to their own morning classes and Felicity did her best to forget about the bodyguard debacle and just focus on AP Chem. Before she even made it to lunch, five people had already stopped her in the hallway to comment on her “dinner date.” Granted, one girl just wanted to know where the coat she had worn was from (Burberry), but by the fifth person, she was contemplating taping a sign to her forehead that read “I know what you’re going to ask, and no.”

Even with all the unwanted inquiries into her love life, the day went by far too quickly and she was dreading heading over to the office to face her dad after her outburst that morning. He wouldn’t get mad at her, he never did. She supposed he felt her owed her that after going MIA for the first five years of her life, even if she didn’t really remember much from when he wasn’t around. No, he would be rational and calm and able to convince her that having a bodyguard was in her best interest, and she didn’t want to break her resolve in less than 24 hours.

On her way to where Sara’s car was parked, she spotted a familiar face standing by the car in the space to the left and she quickened her pace.

“John!”

He looked up and smiled as she barreled into him for a hug.

“Please tell me you’re here to let me know you’re going to be my bodyguard,” she mumbled into his chest, knowing it was just wishful thinking.  

John Diggle had been head of her family’s security detail for years. He was the one who carried her across the property to the house when Sara had tried to teach her how to do a back handspring and it had resulted in a twisted ankle. He was the one who had driven her to her first day of high school and surprised her with Big Belly Burger at lunch. He was the one she trusted completely with her life but never made her feel like she was incompetent to hold her own against the world.

Two years ago though, his wife Lyla had twins, so he resigned to run his own security firm and have more of a 9-5 life. Everyone on her family’s current security detail was contracted and vetted through him. She didn’t get to see him as often as she used to, so this was a nice surprise.

He chuckled and released her, “No. I don’t think Lyla would be up for moving the family across the country.”

Looking up at him, she sighed, “Worth a shot. So what are you doing here?”

“Picking you up from school.” He walked around and opened the passenger seat door for her.

“Oh so I get to sit up front now?” she teased, sliding into the car and pulling out her phone to text Sara and let her know where she disappeared to. Normally she was relegated to the backseat when one of the family security staff was driving her somewhere.

“Well it’s either that or you’re wedged between two car seats,” he replied, closing her door before going around to get into the driver’s side.  “Lyla’s making chicken cacciatore for dinner.”

“Mmm,” she hummed approvingly. “I hope you’re telling me this because I’m invited.”

“Of course. I checked in with your dad and he said it would be okay for you to skip out on work this afternoon. The twins will be excited to see you.”

She raised an eyebrow in surprise, “I’m surprised dad’s letting go of an opportunity to talk me into the bodyguard thing…”

“Felicity,” John began tentatively. “It’s basically a done deal. I started interviewing candidates three days ago.”

She groaned, “Noooo, you’re supposed to be on my side.”

“I am on your side, which is why I’m going to find the perfect person for you,” he assured her. “You trust me, don’t you?”

“Of course I trust you, I just wish my parents trusted me a little bit more to not need a babysitter. It’s one thing to have all the security at home, the family detail shadowing us when we go out together, and occasionally have someone drive me somewhere. Having someone who’s just focused on me 24/7 seems so stifling.”

“If they’re good at their job, and I will ensure that they are, you won’t even notice that they’re around; but it will give your parents peace of mind. You know this isn’t because they don’t trust you, it’s everyone else they’re worried about.”

“Have there been threats?” she asked, remembering her conversation with Sara from that morning and knowing that he wouldn’t hide the truth from her.

“Nothing that hasn’t been easily dealt with. Yet. But you have to remember that not only does your family have a lot of money, they also hold the keys to a lot of people’s important secrets. There’s a lot of information that you could be used as leverage to gain access to, should someone get any ideas. I know your Uncle has his own security, but what about when you’re in Massachusetts during the week? Sending you across the country without protection would be irresponsible of your parents, and me.”

She sighed, “You’re being very aggravatingly convincing.”

“Really? Because I haven’t even gotten to the ‘the twins will cry if something happens to Aunt Felicity’ guilt trip part of my speech.” He glanced over at her with a knowing smile and she rolled her eyes.

She was starting to understand the necessity, but that didn’t mean she had to automatically like the idea of someone following her around all the time, stealing away more of the illusion of normalcy that she attempted in her life.

“You’ll find the perfect person?” she asked quietly, looking down at her hands folded in her lap.

“I promise.”


 

“You asked to see me sir?” Oliver stepped into his boss’ office and he motioned for him to take a seat.

He had been working for John Diggle for almost a year now, primarily doing event security and occasionally subbing for some of the guys who were on personal security details, but he owed him a lot more than just employment. His first meeting with John had been the night that McKenna broke things off with him after her accident. He had run into him in the hallway at the hospital, apparently his wife was in labor and had made him leave the room for a bit because he was fretting too much and she needed to concentrate. They didn't talk for long and Oliver might have completely forgotten the encounter if it wasn't for the fact that three months later he ran into him again. This time it was at an outdoor concert in the park that some of his coworkers at the gym where he had been working at the time had dragged him to, that John’s company was doing event security for. It's a possibility that he might have gotten a little bit… wasted, and that resulted in him dumping his entire tragic life story on the poor guy. Two dead parents in the same year, dropping out of college to take care of little sister—something he never once regretted—but has now limited career options, still not over the girlfriend who dumped him three months ago, the works. John must have taken pity on him, because when he woke up the next morning, he found a business card for Spartan Security in his pocket with a note scribbled on the back. At first he had been a little reluctant to take him up on the job offer. After all, he had a decent job at the gym, but it had started to feel like a dead end of sorts for him. With Thea going to live with an Aunt and Uncle who had recently moved back into town, it seemed like as good a time as any to start focusing on moving forward with his own life again.

Quickly, he found that he liked working in security. He had always been a protective, albeit slightly reckless, person, and John helped him hone those instincts to make him into someone who would throw themselves in between danger and a person, even a complete stranger, effectively and without having to think twice about it. Having to take care of Thea at a young age had forced him to grow up fast in a lot of ways, probably way before he was really ready for that kind of responsibility, but the parts of him that were still an immature boy had been chipped away by this job. He liked to think he had become the kind of man his parents would be proud of if they were still alive; responsible, focused, dedicated.   

“You didn’t put your name in for the Smoak job,” John commented as he sunk into the chair across from him.

“I... umm…” He drummed his fingers on the desk. “I assumed you were looking for someone with more personal security experience. I know she’s pretty high profile.”

Felicity Smoak and her parents had been on the guest list at events he had worked, but he hadn’t paid her much special notice. However, it was hard to miss the big sign that said Kuttler & Smoak on the building that he drove past every day on his way to get to the offices. When John had put out the notice that he was taking applicants to be Felicity’s personal bodyguard, a lot of the guys had clambered at the chance to work for such an esteemed family. The fact that she didn’t seem to be the rich drama queen type who created a TMZ worthy scene every weekend that a lot of them had worked for in the past probably heightened her appeal as well.

“She is,” John affirmed. “She’s also very important to me, as important as my own family, which means I’m looking for a certain kind of person to protect her. That doesn’t necessarily mean the most experienced.”  

“Oh.”

“I’ve interviewed a lot of people over the last few days,” John continued. “And I don’t think any of them are the right fit.”

“And you— are you telling me this because you think I might be the right fit?” he asked, shifting in his seat.

John slid a file across the desk to him, “I want you to look this over and decide first for yourself if you think you’re the right fit. And then I’ll let you know what I think. Okay?”

He nodded and picked up the file, “Okay.”