A/N: Someone asked me to continue this prompt into a second part so hence I have posted it separately to my prompts and will be adding chapter 2 later.
Felicity sighed as she stepped into the bar restaurant. The rain was starting to beat down and she hoped that her date was actually there. Well it wouldn't be an issue if he wasn't, because she had no idea who she was meeting. Iris had set her up on a blind date, the only information she gave away was that he was handsome. That and he'd have a green handkerchief in his top pocket. The hostess quickly ridded her of her coat asking if she was meeting anyone.
"I am but I'm going to go to the bar first." She smiled softly, her red dress flowed over her hips loosely, the alter neck plunging low to the front and revealing skin at the back. She ordered herself a red wine as she looked around the room. Her eyes were trained seeking out green in the sea of black; she finally found the handkerchief on a gentleman on a table near the back. She took a deep breath steeling her spine as she made her way over to him drink in hand.
He had his head down, glued to some form of paperwork as she stepped closer. She coughed a little and his head snapped up. He looked her up and down appreciatively, his eyes wandering over her legs, moving slowly up her dress, briefly stopping at her cleavage before they met hers. She had to do a double take, her eyes widened in shock. It was Oliver Queen. He had piercing blue eyes, a stubbled jaw that could break a woman's heart. A mole at the corner of his very kissable lips and really truly the press didn't do him justice.
"I..." Her mind failed her as she stood there. "I'm meant to be meeting someone on a blind date, my friend totally set me up and I had no idea that it would be someone I know. Well not know exactly, I mean you're my boss." He started grinning his eyes sparkling as he stared at her. "Well not my boss specifically, you're my boss boss though, I mean I do work for your company..." She closed her eyes then taking a deep breath. "Sorry," she mumbled feeling her cheeks flush.
"Don't be," he replied softly, his voice tender. "Please sit." He gestured to the chair opposite him, his smile seeming even more joyful. She gently sat down when a random lady walked over. His smile faded instantly instead replaced by a forced one.
"Oh my god Ollie! What are you doing here?" The dark haired girl asked.
"I'm on a date," he said gesturing towards Felicity. His voice seemed different too, as Felicity watched with intrigue.
"Oh." The woman scowled at her before turning back to Oliver. "Well it was good to see you babe." She leant forward kissing him on the cheek, her bright pink lipstick smudging on his skin. She leant to his ear mock whispering. "When things go south with her you know where to find me." With that she sauntered off, swaying her hips as Oliver turned back to Felicity.
"I'm sorry about... that." He gestured in the general direction of where she had disappeared to.
"No big deal, you're Oliver Queen. Every girls dream right?" She saw him flinch slightly at that before he straightened up, the fake smile he had shown to the lady appearing on his face.
"Well seeing as you know my name, do I get to know yours?" She tilted her head frowning at him. "What? Do I have something on my face?"
"No... I mean yes, that's not what I'm staring at though..." His lips curled up more naturally then even if it was briefly.
"Where?" he asked and she frowned even more.
"Excuse me?"
"Where is whatever is on my face?"
"Oh it's her lipstick, on your cheek."
Instantly he dampened his napkin with his water before rubbing his cheek. "Better?"
"Better." She smiled sipping her wine again.
"So what were you staring at?"
"Your face." He laughed then, as she sighed loudly. "I mean it's a nice face, an attractive face, Jesus you're like a god but I meant... the expressions." He was smiling properly, his eyes never once leaving hers.
"What about them?" He picked his glass up.
"It must be hard." He frowned at her. "Pretending." He stopped his glass mid way to his mouth.
"What do you-"
"Oliver Queen CEO has to be a pretty tough guy, he makes hard and ruthless decisions, and he does the best for his company. I've heard of some of the decisions you've made. Then there is Ollie Queen, ex-playboy, who partied and got drunk, who slept with anything with a pulse. Then there's this whole other Oliver Queen, this one with the fake smiles and gracious politeness like you don't want to offend anyone, but it destroys your soul..." Oliver just stared at her. "Then there is this guy sitting opposite me, the one who isn't plastering on a fake smile. Whose eyes sparkle, and whole face lights up. Who looks like he's carrying the weight of the world on his shoulders with no one to share the load." He swallowed thickly unable to look away.
"I..."
"I'm intrigued by that guy... Because who gets to look after you Oliver, who gets to remind you that you're a good man, who helps you?" She tilted her head staring at him once more.
"How is possible a blonde woman, I've never seen before can figure out all this about me just from sitting opposite me?"
She shrugged. "There's just something about you, you're like an open book to me."
"Ah, not many have described me as that."
"I know, I've read the articles, closed off, guarded, private to name a few." He looked down before he smiled back up at her with a sad glint in his eyes. "It must be really hard and pretty lonely." He just stared at her. "You know I think they have you all wrong."
"You do?" he asked his face expressionless now.
"Yes, I think you are private and rightly so. But the guarded, closed off thing I think that's a safety mechanism, I think you're quite a nice guy, maybe you need to let some people in." She smiled at him warmly as she sipped her wine.
"Ah but it's knowing who to let in, who is interested in me and not my money."
"Very true Mr Queen, but I didn't even know you were my blind date. Actually I wasn't aware Iris even knew you!" she said shaking her head.
Oliver frowned at her. "Iris?"
"Yes she's my best friend, she's a reporter so I guess I shouldn't really be surprised."
Oliver's mouth fell open. "I don't know any Iris."
Felicity instantly looked around her staring at him wide eyed. "Oh god." She dropped her face into her hands. "You aren't here on a blind date are you?" He ran a hand at the back of his neck.
"Yes actually I was. I am, but it was my best friend Tommy who set me up." Felicity pulled her hands away.
"We're on the wrong dates!" she said bluntly. "I was meant to look for a guy with a green handkerchief..."
"Greens my favourite colour," he replied with a soft smile.
"Oh... Well I royal messed this up." She quickly spun her head around searching for another guy with a green handkerchief before spinning back round to face him. "I am so sorry." She jumped to her feet taking a step back and he was up on his too, gently grabbing her arms preventing her from crashing into the passing waitress.
"No need to be sorry," he whispered, his eyes looked over her head and then he took a step back. "It appears your guy is here." He tilted his head to a tall, dark haired gentleman with a bright green handkerchief in his pocket.
"Oh." She couldn't help the wave of disappoint that hit her as the man strode over and Oliver sat back down.
"Felicity Smoak?" he asked and she nodded. "Ray Palmer." He suddenly engulfed her in a hug, and she hesitated, stood there tense as he pulled away.
"Nice to meet you Ray," Felicity replied.
"Our table's over in the corner." He pointed to it. "I just need to use the restroom." He stepped passed her, at the same time a gorgeous brunette slipped by her and introduced herself to Oliver. She saw his fake smile plastered back in place, signalling he wasn't enjoying it either. She took a deep breath walking to the bar.
"Red wine please," she asked the bar tender.
"Put it on my tab," Oliver said softly as he stood beside her.
"You don't have to." She looked up at him.
"I want to Felicity," he replied it smiling down at her.
"Thank you," she responded with a beaming smile, and then Ray was back on her other side.
"Well Felicity, should we get this evening started?" He held out his arm, and she took it cautiously; unable to stop herself glancing back at Oliver who was staring at her too.
Oliver stood there ordering himself and his dates drinks, he'd already made it his mission to find Felicity Smoak and ask her out, even before either of their dates had appeared. But now watching her smiling at another man, he had never quite felt jealousy like this before and he knew he needed her in his life.