A/N: Well, once again, this began as a Trope. Trope #9 to be specific. The 'Felicity needs a date trope'. It was supposed to be short and sweet and not a problem child. At around 12K words I realized that wasn't going to happen. So you get this instead. A new multi-chapter fic that is probably the most fun thing I've ever written.

Thanks to hopedreamlovepray and befitandchase for telling me to just go for it.

Enjoy, and let me know what you think!

The 'Save the Date' website had been left in the background on one of Felicity's screens for the past two weeks. She couldn't bring herself to reply to the email when it had arrived, but she also couldn't close it.

Her cousin, Madison, was getting married in three months time to the exact man she'd set her designs on at the ripe old age of nine and a half. Felicity could remember long, torturous summers at her grandmother's house while Maddie went on and on about the man she was going to marry and how rich he was going to be and how she'd have everything she ever wanted. Felicity wanted a few moments peace to read the latest issue of Popular Science but she never got them.

As they'd gotten older Maddie had turned into someone Felicity couldn't stand. She was vapid, and snobbish, and quick to turn her back on someone, even family, if it helped her out. After a particularly horrible experience when she was fourteen Felicity begged her mother to never have to see her again, and other than a few chance meetings, she hadn't.

The last time they'd been in the same room was during the memorial service for their grandmother three years prior. Felicity had only been working at Queen Consolidated for a couple of months and was happily filling in her uncle, Maddie's father, on her position and the work she was doing when her cousin had sauntered up, made an expectedly acerbic comment and disappeared again.

Felicity knew the only reason she'd been invited to the wedding was so that Maddie could rub her face in it. This was a chance in a lifetime to prove to the world just how well she had done. It was a destination wedding at a small private island two hundred miles off the coast of Starling City. Guests would arrive by chartered boat, to spend three glorious days watching Maddie show herself off.

Felicity's mother had called no less than four times to ask if she'd replied yet. She'd told her she was busy and would get to it soon, but the truth was she couldn't stomach the idea of spending an hour, much less three days with Maddie.

She sighed tiredly as she clicked on the site once again. Her parents were one of the first to send in their rsvp. Maddie's father was Felicity's dad's favorite brother, and she had to admit she had no issue with her aunt and uncle, just their daughter.

She'd been so wrapped up in her thoughts she hadn't heard Oliver sneak up behind her. To be fair though, he moved so light on his feet she rarely heard him, even when she wasn't distracted.

"Madison Smoak," he read over her shoulder, startling her so bad she let out a shriek and scrambled to click back to the bank records she was supposed to be looking at.

"Sister or..." he trailed off, ignoring her minor freak out.

"Cousin," she said quickly. "Spiteful, horrible, stuck up, cousin."

He lifted an eyebrow at the venom in her voice and she flushed, "She must be if she has you talking like that."

She gave him a look over her glasses and settled back in her chair. "Sorry, lots of history there. She's just using this wedding to flaunt her rich, catch of a man. I don't even know if she loves this guy or if he's just a convenient meal ticket. But it's three days of hell. She'll belittle me and use every chance she can to make me feel like I'm a kid again, and my parents want me to go, and...I haven't been able to come up with a good enough excuse not to." she sat back with a sigh.

"Sounds...awful." he said with a grimace. "But if you decide to go, you can have the time, you know that, right?"

She gave him a grateful smile and turned back to her task.

Three days later she rsvp'd, much to her mother's delight.

When the mission popped up last minute and delayed her catching the charter boat with the rest of her family she was secretly relieved. It had even been worth the tirade her mother had gone on when Felicity had told her she wouldn't be able to make it until the next day, telling her she'd had a major work emergency.

Oliver had walked in at the end of the conversation, unfortunately just when she'd lost her cool some.

"Sorry, Mom. Excuse me if I'm not too upset that I'm going to miss out on an extra day of Maddie pushing her massive diamond under my nose and commenting on my lack of a boyfriend! You know it's always one of my favorite pastimes!" she rubbed at her temple to try and alleviate the headache she'd developed.

Silently she handed Oliver his ear piece and mouthed 'Sorry' at him while pointing to the phone.

"Felicity, Maddie is...a bit high strung, but I think it's unfair to accuse her of something that hasn't even happened yet." her mother said, making her head throb. She had never been able to say anything bad about Maddie. "And how do you expect to get out to the island tomorrow. They're not running another boat."

"I'll figure something out, Mom. I'll find a way to the island, don't worry. Ok, look, I've got to go or I won't get out of here tomorrow either. See ya soon, love you, bye." she thumbed off the call before her mother even had a chance to speak.

"Everything okay?" Oliver asked as he loaded his quiver and strapped it on.

"Yeah, it's this damn wedding." she said with a sigh as she turned on the comms link and checked to make sure they were working properly.

"You should take the chopper tomorrow." he said it easily, as if she was borrowing a pen.

She looked at him, incredulous and laughed, "Right, I'll just take the company helicopter to my cousin's wedding."

"Why not? All those islands have landing pads. It's a short flight. And it's my fault you didn't get to leave tonight like you were supposed to. Take it."

Felicity knew she should say something, but she was still in shock.

He walked towards her and cupped her elbow before he leaned in some with a small smirk on his lips, "Besides, you know it would drive your cousin mad if you took some of the attention away from her, even if it was for a moment."

She couldn't help grinning back, and tried to keep her stomach from flipping at how close he was. His fingers trailed down her arm as he stepped away.

"Think about it." he ordered, as he pulled the hood up, and then he was gone.

The mission had gone well. Oliver got what they needed and was back in the lair before midnight.

"Have you made your decision yet?" he asked as he walked towards her, wiping the paint off his eyes.

She scrubbed nervous palms over her thighs and gave him a small smile. "If you're sure..."

His hand clasped her shoulder gently, and she tried to suppress a shiver, "I'll text you the details tomorrow."

All she could do was swallow heavily and nod. As she gathered her things she imagined the look on Maddie's face as she stepped out of the QC chopper, and a huge grin split her face.

Her bags had been packed already, so when she woke up in the morning she had nothing but time to kill as she waited for Oliver's text.

When it came all it said was 'Roof of QC, 11am'.

She felt strange walking through the lobby of Queen Consolidated on a work day towing an overnight bag and wearing a sundress, but luckily no one stopped her for anything business related and soon enough she was in the executive elevator heading to the top floor.

She stopped by Oliver's office on the way, wanting to thank him in person, but he wasn't there. She scribbled a quick note, telling him how much she appreciated his gift and admonishing him and Digg to not get into any trouble while she was gone. She slipped it under the corner of his phone knowing he'd see it.

The roof top access door was tucked away near the emergency stairwell. When she pushed it open she was greeted by the pilot who took her bags. "This way Ms. Smoak." he said professionally and she had a fleeting thought that she could get used to such service.

Bright sunlight made her dig out her sunglasses as they stepped onto the roof. She'd opted to wear her contacts; one less thing for Maddie to ding her on. The blades were already running and she kept her head low as she approached, one hand trying to keep her hair down as it blew all about her.

The door to the chopper was already open and a hand reached out as she approached. Without looking she took it and carefully stepped up. The hand squeezed hers and she gasped as a rush of electricity flared down her arm.

Felicity pushed her glasses up as she slid into the seat and saw Oliver grinning at her proudly. He still hadn't let go of her hand.

"What? What are you doing here?" she asked, shocked.

"I did some thinking last night. And I didn't like how you were talking about your cousin and how she made you see yourself. You're the bravest, smartest, most amazing woman I know, and everyone deserves to see you that way, including yourself." she'd never heard Oliver so earnest before.

Her face flushed at his words, "Oliver..." she began but didn't know what to say, she knew he valued her, but she'd never imagined he'd ever say something like that to her.

"But why are you here?" she asked, confused.

"I'm offering my services." there was a glint in his eyes that made her stomach flip.

"Services?" she asked warily

"As your rich, arm candy." he replied, flashing her his million watt playboy smile.

She knew her mouth had fallen open, but her brain couldn't process what he'd just said.

"You...you're...wait. You want to go to my cousin's wedding with me and...what? Pretend to be my...date?"

Oliver just nodded.

"No...I can't. That's too much. The helicopter is too much. This is ridiculous." she protested, and jumped as the door was slammed shut behind her.

His hand squeezed hers again, "Felicity, I want to. You do so much for me, let me do this for you, please. Come on, it's just another mission, right? Operation make Maddie eat crow." the grin he gave her was light and cajoling and she had a thought that this was probably how he and Tommy had gotten into so much trouble when they were younger.

His eyes held hers and before she knew what she was doing she nodded.

When his hand slid from hers she startled. He tilted his head slightly as he handed her a headset and showed her the setting so they could talk to each other on the flight without the pilot hearing.

She strapped on the harness and waited as Oliver did the same.

"Ready, Mr. Queen?" the pilot asked from his seat as he flipped switches and prepared the helicopter for takeoff.

"Whenever you are." Oliver replied.

Static was cut off as the pilot spoke again. "Flight time is one hour."

She gripped the side of her chair tightly as they began to lift from the roof. She shot Oliver a nervous smile, "Sorry, I've never actually been in a helicopter before." she told him.

"It's perfectly safe." she heard in her ear, but the drone of the engine only let her see his lips moving.

They banked to the right as they headed away from Queen Consolidated and she let out a small eep as she felt herself shift in her seat even though the harness held her securely. Oliver's arm flashed out and landed on her thigh, keeping her in place. She hadn't even realized she'd gripped his forearm until they evened out

The heat of his palm was all she could focus on and she didn't look at him, instead she purposely looked out the window as she watched Starling City from the air.

It seemed to take longer than necessary for his hand to slide back and she knew her cheeks were pink. Her attraction to him had grown into something much much more after he'd returned from his five months away. She didn't know how she would get through the next two days with him pretending to be her date.

Which is why she was dreading bringing it up as they flew towards the island, but they couldn't walk in there without a plan.

"So...you do realize we have no time at all to come up with a cover story." she told him, finally daring to raise her eyes to his.

"Relax. Keep it simple. Isn't that what you tell me?" he told her and she had to agree. "We've been together for a while, but have been quiet because of the press. Simple."

The ease with which he said 'We've been together for a while,' took her breath away and she didn't trust her voice.

When she did speak she didn't look at him. "Yeah, that works just fine."

She pretended to be entranced by the view below them, but really she was trying to get a handle on her emotions which were all over the place and threatening to betray her.

It took her five long minutes before she felt like she wouldn't flush red when she turned. By that point they had stopped following the coastline and were now out above open water. The water glinted off the waves and she could only see the city skyline when she craned her head far to the right.

She looked over at Oliver, about to make a comment about something innocuous when she saw the rigid set of his jaw and the way his hands were clenched.

"Oliver, what's wrong?" she asked immediately, not even noticing she had reached over to lay a hand over his fist.

His head turned towards her slightly and she saw the effort it took him to swallow before he answered her. "Sorry, open water and islands..."

Shame and guilt filled her as she saw how hard he was trying to get himself under control despite the memories that were undoubtably being dragged to the surface.

"Oh my god, I'm so sorry!" she blurted out, "I didn't even think. We'll turn around. You'll see land in a just a few minutes and it'll be fine. Just tell the pilot to turn around." all thoughts of getting to the wedding on time flew from her mind, she just needed him to be okay.

However, her reaction seemed to settle him down some. She felt the tenseness under her hand relax some. Her hand was half raised to cup his jaw when she stopped herself. Instead she canted herself in the seat so her knee pressed against his, giving him something to make contact with.

His eyes shut tight for a long moment, and then she felt his hand open a bit and wrap around her fingers.

"I'll be fine." he said, although his voice was still tight.

She bit her lip in worry as she studied him, still feeling horrible at putting him in this situation. "How about I tell you about my family?" she asked suddenly, looking for anything that could possibly get his mind off of his past.

The corner of his mouth ticked up and his thumb ghosted over her hand, making her shiver. "That sounds good."

For the next thirty minutes she talked without pause. She told him about her parents, her aunt and uncle, more about Maddie. She told him old family stories, about her grandparents and summers at their house outside of Starling City. The longer she talked the more he relaxed. But he never let go of her hand.

She was in the middle of regaling him with a particularly self deprecating tale when the pilot announced they were almost ready to land.

There was a chain of islands below them now. Some small, some larger. All had huge homes on them. She could spot opulent swimming pools and white sand beaches, and more palm trees than she could count.

"That one's ours." Oliver said suddenly, leaning over her to point to one of the larger islands they were just passing over.

"What do you mean?" she asked with a grin,

"My family owns that island. Haven't been there since I was eighteen, almost forgot about it." he said simply and sat back.

She just shook her head at him as they descended. She spotted a larger building and several small ones. The landing pad was near the water and as they touched down she could see that they had arrived during lunch.

"Oh...this was really good timing." she said under her breath, but Oliver heard her through the headset.

"Why's that?" he asked, the strain gone from his eyes now that they were on the ground.

She blushed for a second before she directed his attention out the window.

The main building had a huge open air veranda where tables were set up. Every seat was full with wedding guests, and every set of eyes were on the helicopter that had just landed.

Oliver plucked the headset off her head and undid the harness before she knew what he was doing. She smoothed a hand over her hair and gave him a little smile.

"You ready to do this, Ms. Smoak?" he asked, a hint of mischief in his tone.

"Absolutely, Mr. Queen." she answered.

The pilot opened the door on Oliver's side. He adjusted his jacket and tie and gave her a look that made something grow, low and heavy in her belly, before he climbed out. He had to say her name before she jolted out of her own head and slid her hand into his and followed him.

He didn't release her hand and she used her free one to brush wrinkles from her skirt as nerves struck her. This was insane, she would never be able to pull this off, Maddie would see through it in a second.

Oliver's hand caught her chin and tipped it up, "Hey, this will work, don't worry." he said and she realized she'd said all of that out loud.

And then his mouth was on hers. It was short, and sweet and she barely got to enjoy it before he was pulling back, leaving her stunned.

"Wha..." she barely was able to breathe. Oliver had kissed her.

"I don't get to kiss my girlfriend?" he asked low, the hand that wasn't holding her, falling to rest against her waist.

That part of this charade had never crossed her mind.

His eyes cut over her head, and he leaned in closer to whisper in her ear, "I'm going to assume the woman in pink barreling towards us like an out of control train is your cousin."

The image he'd conjured was enough to make her burst into laughter, her forehead coming to rest against his lapel as she tried to compose herself before she faced her family.

He squeezed her hand again and began to lead them down the paved walk, leaving her no choice but to follow.

She saw Maddie, halfway down the path, and Felicity's parents weren't far behind.

"Lissy!" Maddie cried, between gritted teeth even though there was a perfect smile plastered over top.

Felicity felt her shoulders go back at that dreaded nickname. Maddie had pegged her with it when they were little when she found out Felicity hated it and had never stopped.

"We had no idea you'd be able to make it!" Maddie cried, unable to keep her eyes off of Oliver, she was almost vibrating with her need for an introduction.

"Well, Oliver was able to shuffle his schedule some so we took the chopper. The jet would have been faster but this island is too small for an airport." Felicity replied smoothly, amazed at what had just come from her mouth. From the way Oliver's hand released hers and wrapped about her waist she thought he was impressed as well.

She half turned towards him, her fingers grazing over his tie, trying not to think about where this sudden boldness was coming from, but fairly certain it had to do with the man next to her. "Oliver, this is my cousin Madison Smoak. Maddie, this is Oliver Queen, my...fiance."