A/N: Welcome to my new story, everyone. I finished writing this a few weeks ago and I'll post a new chapter every Wednesday. Thanks goes to my beta reader x. imagine .x (take out the spaces, it just wouldn't let me write it otherwise) for sticking with me through the whole story and doing a fabulous job!

I don't own Arrow or it's characters.

March 4th, 2015

Oliver Queen had everything. He was the most eligible bachelor in Starling City, he lived in one of the best apartments in the city and he was the CEO of one of the largest companies in the country. Women were basically lying at his feet, begging to be the future 'Mrs. Queen'. He lived a perfect life, but he didn't care about any of it.

It all started when his father passed away a few months ago. Suddenly, nothing mattered anymore, not the money or the women. He stopped caring about it all.

He had just moved out of the mansion, needing his own space, when is mother called him in tears, telling him that his father, Robert Queen, had a heart attack.

Oliver didn't know how he made it to Starling General; all he knew when he got the call was that he had to get there as quickly as possible. He ran blindly through the corridors, desperate for any sign of them, until one of the nurses stopped him.

"Sir, can I help you?" She asked, laying her hand on his shoulder. Her tone was friendly, but he barely registered it through his panic.

"I... my father, Robert Queen, was brought here. He had a heart attack. I'm looking for my mother and sister. They said they would be here," he whispered after taking several deep breaths. He had to be strong.

"Alright, let me bring you to the emergency room waiting area. They will probably be there", the nurse told him. He didn't resist when she began gently pushing him down the corridor.

After walking for several minutes, they entered a rather large room. His mother and Thea were huddle together in the corner.

"Ollie!" His sister cried. Seconds later, she was hugging him, crying hysterically. She had just turned 18 years old a few months ago and was finishing high school this year.

"It's alright. I'm here, Speedy," he tried to assure her, but taking a look at his mother made his stomach churn.

Moira Queen was staring blankly at the opposite wall of the waiting room. In her hand, she was clutching a white handkerchief and silent tears where running down her face.

It took him one look to know his father didn't make it.

"Mom," he muttered quietly, maneuvering Thea and himself next to her on the chairs.

She looked up to him and it almost broke his heart. His normally strong mother was at a loss for words, her eyes emotionless.

"He is dead, Oliver. Your father is dead," she breathed. Thea next to him, started crying louder.

Oliver felt his throat closing and he swallowed hard. There was an aching pain in his chest. Taking long, deep breaths and closing his eyes for a moment, he enveloped his mother in his arms, letting her cry on his shoulder.

He had to be the strong one from now on. His father wasn't here anymore to hold the family together. It was his turn to step up.

The following weeks were brutal. He became the CEO of Queen Consolidated, their family's company, following in his father's footsteps. He stopped drinking, partying, and sleeping around with random women. He even moved back to the mansion for the first two weeks, trying to be there for his mother and sister, but it quickly became too much, and he moved back to his apartment.

They were never the perfect family everyone assumed. Moira and Robert argued, sometimes to the point Oliver wasn't even sure if they really loved each other. His sister didn't seem to care about anything beyond the latest fashion and refused to go to college after high school. Granted, nobody seemed to except anything else from her. He certainly wasn't a good role model for her. In fact, he was probably one of the main reasons his family was far from perfect underneath the surface.

Now, a few months later, he still missed his father, but he never wished for his old life back. He didn't miss the raging parties, or the meaningless one-night stands. He actually enjoyed the stability of his life now that he had a job and more responsibility than simply making the occasional appearance in public.

Nevertheless, he hadn't earned his job; it was handed to him, like everything else in his life. After two years at Harvard pursuing a business degree, he was kicked out for conduct unbecoming to the school's public image. Of course, nobody officially expelled him; he left the school for "private reasons," but everyone who knew him realized it was just another lie to cover up his over-the-top escapades. After all, it was the second school he left after Princeton.

His parents didn't try to send him to another school after that. Instead, he moved back home and reunited with his friend, Tommy, living up to his reputation in full. Having Tommy around, living the exact same life, didn't help. If anything, he made it worse.

Looking back, Oliver knew how stupid he was. He was a young, spoiled kid with everything he wanted available at the snap of his fingers, but he took it all for granted.

Today, sitting in his office and reading an article about a new project in Applied Sciences, he wished that he had listened more at the lectures and cared less about the pretty girls sitting in front of him. It was hard, making the right decisions for the company, even though his executive assistant, Martha, tried to help him with everything she could.

Right at that moment, Martha pushed into his office, talking as she approached his desk. "Here is the schedule for the afternoon, Mr. Queen. Looks like it will be a late night again."

He let out a frustrated groan, running a hand through his hair. "Great."

"I can stay longer, too, you know", Martha suggested, shooting him a sympathetic glance.

He looked at her sternly, shaking his head. "No, Martha. We have an agreement remember? No overtime."

The brunette opened her mouth to protest, but closed it again at his stare and gave him a smile in surrender. She was always happy and thankful to go home at a decent time to be with her husband and child. It was the least Oliver could do, after all she did for him. She knew more about the company than he did, and she was always able to answer his questions. She was a life saver.

Once Martha left his office, he finished reading his article. Glancing at the clock, he saw that it was time for his lunch break and sighed in relief. He gathered his suit jacket and wallet before heading out of the office via the elevator.

Normally, he ordered in, but last week, he discovered a small café down the street from Queen Consolidated. It was now his favorite lunch spot, and not just for food.

Bill Taylor's presentation about the new project for the Applied Sciences department finally wrapped up, and after looking at this watch, Oliver realized he had exactly 20 minutes before his next meeting was going to start. He was in desperate need of another coffee if he hoped to survive the afternoon.

Unfortunately, the coffee machine in the break room broke this morning, which left him with no choice but to make a run to a coffee shop. Quickly excusing himself, he jogged out of the meeting room and headed for the small coffee shop he passed every morning on the way to work.

On the way, he sent a quick text to Martha, asking for her coffee preference. He never allowed her to make coffee for him, not wanting to be one of those arrogant people who misused their assistants.

Entering the small coffee shop, he was immediately hit with the amazing aroma of freshly brewed coffee. From that moment on, he knew he was going to love this coffee shop. He placed his order and proceeded to the waiting area. Checking his phone, he saw that he still had about 10 minutes left. That was when he first laid eyes on Felicity.

Oliver was immediately mesmerized by the blonde ponytail falling smoothly down her back and the blue eyes hidden behind thick, black glasses. He couldn't take his eyes off her as she moved flawlessly behind the counter, preparing some kind of beverage without bumping into any of her co-workers. Her lips, colored to match the dark purple dress she wore under her apron, pressed together as she hummed softly along with the song on the radio, not bothered by the noise level.

Something clicked, watching this woman prepare his coffee. For the first time in months, Oliver felt like his life made sense, like there was something to live for again.

He wasn't the type of man who liked to commit, his longest relationship lasting about three months. When that failed, he stopped trying the whole commitment thing, not wanting to be tied to only one person for too long.

But everything seemed different with the blonde woman behind the counter. His first thought wasn't how to get her to sleep with him; he didn't even think about how good she looked in her dress, or about her long, smooth legs exposed by its mid-thigh hemline. He simply wanted to talk to her.

"Two grande coffees for Oliver," the blonde girl called, scanning the room for him. He quickly moved forward, catching her eye and flashing her a wide smile. He made a point to look at her name tag when he grabbed the two coffees.

"Thank you, Felicity," he replied, winking at her and trying to hold the eye contact just a second longer. She only gave him a small smile before starting to prepare the next drink.

Astounded, he left the small coffee shop, heading back to his office. No woman had ever been immune to his charm or smile, but Felicity didn't seem to care. He was even more intrigued by her, if that was possible, and she didn't leave his mind all day.

Now, a week later, he still only got small smiles from her. Every single workday since last Tuesday, he went to the small coffee shop and had lunch there. Yes, he actually sat there, eating some kind of pastry or sandwich and drinking his coffee, glancing at her every now and then.

Even her co-workers noticed. He saw them, whispering in her ear, discreetly pointing in his direction. She didn't seem to mind, only nodding and giving them a small smile before continuing with her work.

He tried everything. He complimented her on her dresses and her eyes. He even told her that he liked the color of her fingernails. Felicity, however, simply smiled at him, muttering a small 'Thank you' before returning to her work.

Entering the coffee shop, he already had another compliment worked up. He wasn't going to give up easily. Scanning the little counter area for her, he deflated when he noticed she wasn't there.

He ordered a coffee and a sandwich, trying to hide his disappointment, but apparently, he wasn't doing a very good job of it.

"She's sitting over there. It's her lunch break," the blonde barista, Sara, told him, nodding her head to the back of the shop.

Surprised, he looked up at her after glancing to the back and seeing Felicity sitting at one of the tables.

"Thank you," he said, smiling brightly.

Today was his lucky day. He waited impatiently for his coffee and sandwich, the process seeming to take twice as long today. Finally, someone called his name and he snatched the two things before heading to her table.

Taking a deep breath, he stopped in front of her.

"Is this seat taken?" He asked, giving her one of his charming smiles.

Confused, Felicity looked up at him. She was reading a book, but quickly closed it and put it in her bag at the sight of him.

"I'm sorry, am I interrupting something?" He apologized, sitting down at the opposite side of the table without waiting for her answer. "I just saw you sitting here alone and thought that you might enjoy the company."

She raised her eyebrows and nervously fiddled with her coffee cup. "What made you think I wasn't enjoying my book?" She responded, taking him aback.

"Alright, you caught me. I've been trying to get you to talk to me for a week now, and all I get are little smiles. Don't get me wrong, they're cute, but what does it take to have a conversation with you?" Oliver confessed, taking a sip from his coffee.

"I'm not your type, Mr. Queen. You're clearly talking to the wrong person," she countered, grabbing her coffee and getting ready to leave.

"What? Wait, no Felicity," he called out, grabbing her arm to keep her in place. "You totally misunderstood me. I only want to talk to you, no strings attached. Please," he implored, using his grip on her arm to guide her down to the seat once more. "To be honest, you fascinate me, Felicity, and I would really like to get to know you. Give me one chance, and if I blow it, I won't bother you again."

She eyed him suspiciously and toyed with her coffee cup again. She seemed like she was having an inner battle with herself, debating whether she should say 'Yes' or 'No'.

Oliver just looked hopefully at her. What was he supposed to do if she said no? He hadn't considered that and already cursed himself for it. He didn't want to give up on her, and he was sure she was single. She wasn't wearing a ring, and she would have told him by now if she had a boyfriend.

He looked at her again and she still seemed unsure.

"Please, Felicity. Let's just talk and then you can decide. There's no harm in that, is there?" He tried to persuade her, leaning forward and giving her an innocent smile.

"Why me? I'm not a leggy model or some kind of rich heiress; I work in a coffee shop and live a simple life. There's nothing special about me, Mr. Queen. So why the sudden interest?" She asked, lowering her eyes.

"That's the whole point, Felicity. You aren't like those women. You obviously don't care about what I think. Or about anything else I do, for that matter. You intrigue me, and I would really like to get to know you better," he admitted, trying to catch her eyes again.

The blonde gazed at him across the table, wonder and surprise marking her face. Lowering her eyes once more, she took a deep breath.

"I'll probably regret this, but I'm going to give you one chance, Mr. Queen. I still don't understand it, but the moment I think you're using me... I'm out. I won't change for you," she stated, looking him square in the eyes.

Oliver's small smile stretched into a huge grin. "You won't regret this," he swore gently, taking a relieved sip from his coffee.

She nodded, a soft smile on her lips that warmed his insides.

He held out his hand to her, introducing himself.

"Hi, I'm Oliver Queen. It's nice to meet you."

"Felicity Smoak. It's nice to meet you too," the barista said, shaking his hand. Little did she know that Oliver Queen was going to turn her life upside down.