Disclaimer: I don't own Arrow or anything associated with it. I wrote the exact scene in 1x02 with Oliver, Digg, and Moira just to give a sense of where the story is set plot wise so I obviously don't own that either.
Five years ago, Oliver would've jumped at the chance to be featured in the Starling City Magazine but he wasn't the same man anymore - he hadn't been for a while – and he was fairly certain the editors didn't want present-day Oliver.
Oliver knew that his chances of ditching the photo shoot were slim. His mother had pulled some strings for the prodigal son to be featured in the magazine and while he hated everything about it, Moira thought it was a great idea and was already invested in it. If only ditching his mother's photo shoots were as easy as ditching her body guards.
Starling City Magazine no doubt wanted the old Oliver. The Oliver Starling City loved to hate so many years ago. The billionaire womanizer who could have any girl in the city in his bed within the hour. But that man died on the island.
No matter how different he was now, he didn't have a choice but to play his part for the sake of his alter ego, the vigilante.
Jogging down the stairs of the Queen mansion, he saw his mother sipping her coffee as she paced around the living room, Diggle a few feet away from her. He could vaguely hear a conversation between the two and let out a long sigh, annoyed at his mother's persistence.
"Ma'am, I truly do not know," Diggle shook his head just as Oliver entered the room.
"And he truly doesn't." Oliver added quickly which caused both his mother and his bodyguard to turn to look at him.
"Then perhaps you'd like to share with me where it is you run off to?" Moira asked her son, an understandably exasperated look on her face. Oliver hated lying to his mother but he knew it was out of his hands. He didn't have a choice but to lie to protect her.
Chuckling under his breath, he shrugged nonchalantly, much like pre-island Oliver would have, but then stopped abruptly, staring at his mother.
"I've been alone for five years."
"I know that, Olive—"
"Mom," He cut her off quickly, his eyebrows rising. "Alone."
"I see," was all Moira replied, defeated.
"I promise to introduce her if it ever gets to the…" Oliver trailed off, his trademark smirk on his lips. "Exchanging first names stage…" He chuckled to himself again. The idea that he would be having such meetings just a week after his return was absurd but it wasn't as absurd to assume pre-island Oliver would be having them. In fact, it was expected and even encouraged by people like Tommy.
"I'd rather you promise to take Mr. Diggle with you on your next rendezvous." Moira insisted, approaching her son. "It's not safe. You've already been abducted once. There is a maniac out there hunting the wealthy!"
"The maniac saved my life." Oliver was quick to remind her. It was ironic that the man his mother was trying to protect him from so much was actually himself. He tried not to read into that too much.
"This isn't a game." Moira glared at Oliver, bothered at the way her son refused to take her seriously. "I lost you once." She added, her voice cracking, and Oliver's guilt crept in much stronger than before. "And I am not going through that again."
"Okay," was Oliver's reply with a nod of his head, unable to find it in him to argue any further.
"Digg's my guy." He added after a few seconds, glancing over at the older man and back to his mother.
"Thank you," Moira breathed a sigh as she walked past Oliver and towards the foyer, leaving Diggle and him alone in the living room. Had he known lying to his family would be this hard, he surely would've second guessed his mission.
"Sorry to give you so much grief," Oliver said to finally break the silence between the two of them.
"I served three tours in Afghanistan, Mr. Queen. You don't even come close to my definition of grief." Diggle replied as he slipped his hands out of his pockets and buttoned his suit, walking towards him.
"I'll tell you what." He paused, standing right beside Oliver now. "You ditch me one more time, no one will have to fire me." He nodded sternly, a nod Oliver mirrored a split second later. "I'll wait for you by the car." Diggle added before making his way outside.
A long sigh escaped Oliver's lips and he stood there alone in the living room for just under a minute before glancing at his watch. It was currently 8:32 am and his call time for the photo shoot was exactly two minutes ago. Some things never change.
Oliver headed outside to where Diggle was waiting for him by the black car and nodded his head again as the door was opened for him. Nodding seemed to be their preferred mode of communication between the two. Slipping into the car, he unbuttoned his suit jacket and adjusted himself in the back seat, leaning against the door moments after Diggle shut it.
"God, I'm hungry." He blurted out as soon as Diggle turned the keys in the ignition and started the car. Oliver hadn't had his coffee yet as his mother had sidetracked him before he could do so.
"Would you like me to stop somewhere for breakfast?" Diggle offered, turning his head to look at him as they pulled up to the gate.
"Hm," Oliver thought for a second but then shook his head. "No, that's alright. I'm sure they'll would have tons of muffins for me." He chuckled; attempting to enjoy this at least a little bit. "I hope they have blueberry." Diggle was clearly not amused which only caused Oliver to chuckle even more, this time a bit more discreetly.
It was a fairly uneventful drive to the studio with the usual rush hour traffic jam and morning radio talk show playing in the background but Oliver wasn't paying attention. All he could think about was his next target on the list, which was why he didn't notice they were pulling up at the lot until Diggle stopped the car.
Getting out of the car before Diggle could open the door for him, Oliver realized he'd been here many years before. He was pretty sure this was the same location for another shoot he did but his memory of that was foggy. Most of his memories of that time were.
"Good morning, Mr. Queen," the doorman nodded as he opened the door and stepped aside to let him in. Diggle followed close behind him.
"It's Oliver." He corrected quickly, nodding his head as he walked inside. He hated being called Mr. Queen. Mr. Queen was his father. He was Oliver, just Oliver. Being called Mr. Queen instantly made him relive the last moments of his father's life, an event he'd been trying to forget from the second it happened. It wasn't going very well.
"Well, if it isn't Mr. Queen…" A pony-tailed blonde holding a clipboard noted in an annoyance, approaching him quickly as if on a mission. She was wearing a pastel button down shirt tucked into a pencil skirt and her hair was tied up in a ponytail.
Oliver couldn't help but chuckle at the blonde, tilting his head at her as she spoke quickly. "Oliver. Call me Oliver." He interrupted but it was obvious that she didn't hear him, too caught up in her own words, which made him grin.
"Do you even own a watch?" She asked just as she looked down at his left arm, noticing the rather large watch on his wrist. "Well, obviously, you do, I mean, you're Oliver Queen. Why wouldn't you own a watch? You're probably one of the richest men in Starling City, if not the richest—Anyway..." The blonde cut herself off, taking a deep breath before looking up at him again.
"Do you know what time it is?" She glanced at her own watch. "It's 9:04! Your call time was at 8:30. That was exactly 34 minutes ago! I guess punctuality won't be one of the many adjectives used to describe your incredibly handsome… everything." She motioned to his body with her right hand before snapping herself out of it with a shake of her head, her cheeks now flushed.
Oliver laughed to himself, his eyebrow raised, and turned to see Diggle with a slightly bemused expression as well. "Thank you," He turned back to the much shorter blonde and thanked her for the backhanded compliment.
"There was, um, traffic on the way here." While that wasn't entirely true, he wasn't lying either. There had been traffic on the way to the studio. She didn't need to know that it was mostly because of the time they left the Queen mansion.
"Right." She smiled awkwardly, motioning for him to follow her to the elevator. "I'm Felicity. Felicity Smoak." She introduced herself as she pressed to call down the elevator. "I'm the master tech for Aidan Matthews. He's your photographer. That is, if he still wants to be." She mumbled the last sentence as she stepped inside the elevator and pressed floor number three.
"I'm not the master tech. I'm actually the only tech. I like to tell people I'm the master tech because it makes me sound so much more important," She rambled, closing her eyes shut as if that would make her mouth stop talking and, to Oliver's surprise, it actually did. He could've sworn he heard her muttering numbers though.
Following her inside, Oliver did his best to hold back a grin at Felicity's behavior. Her annoyance at his tardiness was downright adorable and had he known he was going to be greeted by such a beautiful woman, he surely would've hurried. Well, at least the old Oliver would've.
"It's nice to meet you, Felicity. I'm Oliver and this is Diggle." He motioned to the much taller man beside him.
"I know who you are." Felicity interrupted him, rolling her eyes, as if she was offended that he'd even think to introduce himself. "Everyone knows who you are." She muttered under her breath, leading him out of the elevator and into the bright studio. She seemed to have some sort of personal vendetta against him but he struggled to deduce if it was because of his tardiness today or if it ran deeper than that.
"Follow me." She told him before making her way towards the table stocked with clothes all in his size. Oliver glanced at Diggle with raised eyebrows before following the blonde. This was surely not the welcome they were expecting.
"Oliver!" A vaguely familiar brunette rushed towards him and wrapped her arms around his neck, pressing her body against his. "Hey," He murmured confusedly in reply, his arms wrapping around her loosely. Before she pulled away, her lips pressed against his cheek, dangerously close to his lips.
"It's really good to see you again," She told him, a mischievous smirk on her lips with her left hand on his cheek. Felicity was now turned around with her arms crossed, glaring with disapproval at his little detour.
"Yeah," He nodded, unaware of whom he was currently holding. It was obvious he slept with this brunette so many years ago but he couldn't, for the life of him, remember her name and that familiar guilt crept back in. "How have you been?" He asked absentmindedly, combing his brain to see if he could remember anything about her.
Realizing that this might be exactly what he needed to jumpstart the whole façade he was going for in this shoot: jerk billionaire playboy Oliver Queen, he decided to jump right in.
"I'm sorry, what's your name?" Oliver asked, cutting her off abruptly, with his arms still on the brunette's waist. The brunette's expression went from elated to offended in 0.3 seconds but his grin stood its ground.
It didn't take long for Felicity to scoff rather loudly and continue walking to their original destination, ignoring the fact that Oliver was no longer following.
It was going to be a long day.