Author's Note: I hope I've done this chapter justice. I know a lot of people have been anticipating it. Speaking of which, THANK YOU everyone for your outpouring of love and support for this story already. I'm completely overwhelmed! I'm sorry I was unable to post an update yesterday, but I had real life stuff to attend and not much time for beta-ing my chapter. I'm hoping that won't be the issue with the next chapter and am able to post tomorrow. My rough plan is to post a chapter a day. Anyhow, thank you for reading and for all your comments and reviews and kudos and reblogs... it means the world to me!

Oliver stepped off the elevator at the fourth floor and headed directly to the small office that adjoined the server room where he knew he'd find Felicity. His visits down here had become more and more frequent since he'd first sought out help from the IT department two years ago.

He'd come down here with a busted laptop and a recommendation from Walter that he seek out what his stepfather considered the most valuable asset in QC's IT department, if not the whole company. He'd found her with a red pen in her mouth and blue eyes wide behind her thick rimmed glasses. He'd been on-again with Laurel at the time but even so, he had noticed Felicity was an attractive woman. She wasn't at all the type he generally pursued, but there was no denying the appeal of her plush, brightly painted lips, her shiny blonde ponytail and her sparkling blue eyes.

Oliver stopped in at the men's room just down the hall from the elevator bank to use the facilities and wash up. While he was drying his hands, he recalled that first meeting with Felicity and a chuckle bubbled out of his throat despite his dire situation. That was Felicity though, she could always make him laugh.

She'd been so startled to see him standing there in her office that her mouth fell open when he introduced himself. Then, she'd launched into an epic babble about how she knew who he was, the CEO of Queen Consolidated, heir to the empire and son of the late Robert Queen… Her blush when she realized what she was saying had charmed him. When was the last time he'd seen a woman truly blush?

He'd produced his laptop then, and explained that he'd gotten her name from Walter and that he'd accidentally spilled a latte on the device at his favorite coffee shop the day before. He told her he understood that the hardware might be shot, but was hoping she could help him extract the data saved on the hard drive. He'd been working on a presentation for the QC board all week long and he hated to lose all that progress, not to mention all the personal photographs and music he had stored on the hard drive as well.

Felicity had relaxed before his eyes as she took the laptop from him and he watched, enthralled, as she entered her zone. Oliver pulled up a spare chair and watched her work, deftly taking apart the laptop and hooking various cables up to other devices. She excused herself for a moment before returning with a small black boxy object which she explained was a new external hard drive that she would migrate all his data to.

It took her all of twenty minutes to save his professional life (or at least, the next few nights that he would have had to spend redoing the entire presentation). She told him to go purchase a new laptop and then bring it back and she'd help him get all the data set up on the new device. When she was done, she'd promised, it'd be like nothing had ever happened to his original laptop.

And she was right. After that, Oliver had returned to her office often. Sometimes it was with a legitimate problem ("Your email doesn't work because that last spammy porn email you opened had a trojan in it and it corrupted the account, Oliver. You have to be more careful with your email address!") and sometimes it was just because he wanted to talk to her.

Felicity was fun to talk to. She had a great sense of humor and an easy laugh, which always managed to draw a laugh from him as well. And laughing wasn't something he'd done a lot of since his father's death. Her dry wit appealed to him and her reactions to things never failed to brighten his day. He begun inviting her out on coffee breaks and even took his lunch with her several times a month. She was the closest thing he had to a female friend, outside of Sara. And Sara didn't really count because of the whole sex thing anyhow. Besides, he could never talk to Sara about things in his life like he could Felicity. They weren't that sort of friends.

After he knew Felicity for about half a year, Oliver found he could talk to her about the pressures of running the company, about his mother and their complicated relationship, about his regrets about his relationship with his father, about Tommy and Laurel and Thea… She was always happy to listen and offer advice when he needed it. She didn't talk about herself very much but whenever he asked, she assured him it was because there wasn't much to tell. He'd let her get away with that excuse because it seemed important to her but he knew there had to be something she was holding back.

Either way, Oliver trusted Felicity Smoak more than any other woman he knew and he trusted her with the favor he had to ask of her. God, he hated to ask this of her, it was the worst sort of imposition, but he was out of options. Right now, Helena Bertinelli was definitely not an option he wanted to consider.

Oliver reached the open door to her tiny closet of an office and rapped his knuckles on the wood. He watched, charmed, as her head popped up from the bits of wiring and circuitry she'd been examining.

"Oliver! What brings you down to the dungeon today?" she asked, smirking as she set what she was working on aside.

He walked over to her desk and sat in the extra chair with an exaggerated plop. "I have a terrible favor to ask of you."

"What'd you spill a latte on this time?" she asked, winking at him as she turned in her swivel chair to face him.

Oliver took a deep breath and let his eyes travel over her for a minute. Could he make this work? Would his mother question her suitability? Dressed in her standard brightly colored button-down blouse and pencil skirt, she looked nice but not remarkable. He thought she was pretty, beautiful even, had since he'd first met her, but with her hair pulled back into its ever-present ponytail and her glasses, she could easily fade into the background in any crowd. And he knew she preferred to do just that. Would his mother, who sadly knew all about his preferences when it came to women, question his relationship with her on sight?

"No lattes, I promise. But, I have a situation. See, my mother is insisting the family all get together at the Queen family cabin in the mountains for Christmas this year. I have to be there," he explained.

Felicity hummed. "I thought you were going to Aruba with Tommy."

"I had to change my plans. My mother is…. Very insistent."

She shuddered dramatically. "I believe it. All right, so what's the problem? Are you in charge of bringing the pie? Do you need my grandmother's pumpkin pie recipe?"

"No, it's not about pie." He paused and took a deep breath. How could he ask this of her? What other choice did he have? "It's much, much worse."

"Okay, you're starting to scare me. What is it? And why are you here talking to me about it?"

Okay, best to just to get it out there. "I told my mother I would be bringing my girlfriend. I told her we were seriously seeing one another."

"Okay? Wait, you're seeing someone? I thought you and Laurel broke up? Did you meet someone new?" A little line formed between her eyebrows and on any other occasion, Oliver might have thought it was adorable. Right now, he was far too stressed out for that sort of simple musing.

"No, no." Oliver shook his head. "I'm not seeing anyone. Felicity, I made it up to get my mother off my back except now I need someone to bring with me."

"Oh," she said, her brow furrowing more. Then, the lines smoothed out as her eyes widened. Yep, she was getting it. "Oh! Oliver, you want— you can't be— Wait, are you asking me—?"

He sighed. "Yeah, I am. I know it's a lot to ask, Felicity, and I'm sorry but there's literally no one else I can ask."

"What about Sara?" He'd told her all about Sara, of course, and while she'd been disappointed in how he'd treated Laurel there'd not been a whole lot of judgement from her. Just a listening ear.

"She's doing Christmas with her dad and Laurel. Any other girl I'm going to ask is going to get the wrong idea. I need someone who won't expect anything past the holidays."

Felicity was looking at him with an unreadable expression. "You know I don't even celebrate Christmas, right?"

He blew out a breath. Trust Felicity not to make this easy on him. "Yes, you're Jewish. I know. I brought you a Hanukkah gift on the 8th night last year, remember?

She smiled and a blush lit her cheeks as she looked down at her hands. Oliver couldn't fight the grin. "Yeah, I remember. Still… isn't that going to be a problem?"

He shrugged. "I don't see why it would be. They won't care. Or, we don't have to tell them you're Jewish if you don't want."

She looked skeptical. "I find that hard to believe. Okay, she might not care that I'm Jewish, but I'm willing to bet Moira Queen would care about my image. I mean, if you really want to sell this, is she going to believe that her son would marry someone who wore panda flats to work?"

The fact that she was voicing one of his concerns didn't escape him. "We can take care of that no problem," he told her. "The big hurdle is you agreeing to do me this monumental favor."

"Do you even really know what you're asking me to do, Oliver? You're asking me to pose as your girlfriend for… how many days is it?"

"We'll need to be up there on Tuesday afternoon at the latest, and I'm sure my mother will expect us to stay through Friday at least and will try to talk us into staying until Sunday."

"That's three days from now. Three? Four? That doesn't give us a lot of time to work on a story."

Oliver waved a hand. "We can keep it simple, keep it close to the truth. That would be most believable."

Felicity glanced at him from under her lashes. "Yes, well, you would know all there is about lying, wouldn't you?" He fought a flinch. He knew Felicity didn't approve of his lying, had told him in the past that he was better than that in fact, but was this really a lie? Maybe it was more of a… ruse.

"Please, Felicity? I know I ask a lot of favors from you and this is a huge one. I would owe you big time."

She sat back in her chair and tapped an index finger against her lips. The sparkle was back in her blue eyes. "Hmm. Really? Like what?"

"Anything you want."

He remembered her fondness for red wine. "I have a Lafite Rothschild 1982 in the wine cellar that's all yours. Just say the word."

"Seriously? Oliver, do you know what a bottle of that is worth?"

"I do. And it'd be worth it to me if you'll do this."

"Wow, that's tempting." She bit into her lower lip and rocked in her chair a little. "I don't know, though, Oliver. I was really looking forward to a few days at home by myself, just my cozy TARDIS blanket and my DVR full of tv shows to catch up on…"

Oliver remembered then something Felicity had once said, partially in jest, about getting to Walter through Oliver in order to boost her prospects within the company. "Walter will be there."

She perked up noticeably. "He will?"

"Of course. It's a family holiday deal. My sister and her boyfriend, my mom and her husband and… us."

Felicity was quiet for a few moments. She was clearly struggling with the decision. "Can I think about it?"

"We've only got a few days, Felicity."

"I just need tonight. Please? I promise I will think hard, it's just… this is huge, Oliver."

He sighed. "Okay. You have my number?"

She tapped a finger on her cellphone, which sat at the corner of her desk. "Yes, I do."

Oliver stood and smiled at her. "Thanks, Felicity. And please do consider it. I… I wouldn't ask this of you if I wasn't completely desperate."

"I know," she replied. Her eyes were sad as he turned and walked out of her office. He expelled a breath, trying to calm his racing nerves. Since when had he ever been nervous around Felicity?

Felicity Smoak barely got any work done for the rest of the day after Oliver's visit to her office. Her mind was definitely not on the coding she was supposed to be doing, nor was it on the service calls she had to take up on the sixteenth floor. When five o'clock came around, she grabbed her things and gratefully left, happy to have the freedom to think.

All the way back to her tiny townhouse in her little red Mini Cooper, she thought about what Oliver had asked her. Maybe in some other lifetime she would have been thrilled to be asked to pretend to be his girlfriend. It was a dream come true, right? He was a gorgeous man, something she'd noticed from the first moment they'd met two years ago. Then, she'd gotten to know him. He'd let her see underneath the public mask he wore, at the real person he was underneath. Felicity had the impression Oliver didn't let many people see that side of him. The more he came to see her, the more she saw that side of him.

And the more she saw him, the more she fell in love with him.

Falling in love with Oliver Queen was a terrible idea and Felicity had tried desperately not to let it happen. At first, she wondered if it was just her stifled social life that was the reason she was falling under his beguiling spell. For weeks, she'd made an effort. She'd gone out to clubs with friends from work, had accepted date requests from various men and had tried to expand her limited horizons a little bit. Going out with friends had been fun, but the dates had been terrible ideas. Each date was successively worse than the one before and all of those men had been poor imitations of the man she'd tried so hard to forget.

When he'd given her the Hanukkah gift last year, that was when Felicity had finally had to admit to herself that her heart was lost to him. It was just a simple necklace with a little silver star pendant. Probably a drop in the bucket to a man with means like Oliver Queen. But it was beautiful and it was for her and he seemed so pleased to see that she liked it. She put it on and hadn't taken it off except to shower the whole year.

Now he was asking her to pretend to be his girlfriend? To his family?

Felicity parked her Mini Cooper outside her townhouse and locked it up before walking to her door and letting herself inside. The townhouse was small and cozy, decorated with her tastes and it felt cozy and homey to her. But it was empty and quiet. And lonely. She'd been on her own since college. Since before then, if she was being honest. Her mother still lived in Vegas and they didn't see each other very often which was fine by Felicity. The two of them didn't have much in common. It might be nice to spend the holiday with a family, even if it wasn't her own and even if she didn't celebrate the holiday herself.

She went through the motions of fixing herself something to eat for dinner and sitting down in front of her television to watch one of her favorite shows. She even lit her menorah using the shamash candle she had left nearby and reciting the two blessings of Hanukkah as she did so. But her heart just wasn't in the ritual. Her mind kept drifting to spending Christmas with Oliver and his family.

It wasn't as though she wouldn't get something out of the trip, she told herself. There was that promised bottle of wine which was nothing to sneeze at. And then there was the potential to make a significant vocational connection with Walter Steele. One could say that being friends with the QC CEO was connection enough, but Walter was overseeing the development of the new Applied Sciences division personally and she had her eyes on a promotion to that division. Applied Sciences was right up her alley and she wanted that job so badly she could almost taste it. Her interactions with Walter to date had been professional and brief and clearly she'd made a good enough impression on him to warrant him recommending her services to Oliver. Surely, a little more face time would only improve her chances when the hiring began, right?

Then, there was the potential for connecting with Oliver. Felicity hated to even consider it, remembering how Oliver had explained he was asking her because he needed someone who wasn't going to expect anything from him after the trip was over with. But still, she had hope. As pathetic as it was, she had hope.

Biting her lip, Felicity reached for her cell phone and flicked it on. She scrolled to Oliver's phone number in her contacts and stared at the picture she'd snapped of him to go with his contact information. He grinned back at her, blissfully unaware of her attraction to him. Could she do this? Could she really pull this off?

Sighing, she tapped the "call" icon and held the phone to her ear.

"So wait, back up." Tommy set his drink down on the table and held his hand up. "You're bringing Felicity to your family's cabin for a family Christmas?"

"Well, she hasn't said she'd do it yet…"

"I thought you wanted to get back with Laurel?" he asked, his voice rising over the steady thump of the music from the lower level of the club. They were ensconced in a booth in the VIP section, a benefit to being two of Starling City's beloved sons. "Which, I must reiterate, is a bad idea."

Oliver swallowed a groan as he sat back in their booth, taking a long drink of the Scotch he had in front of him. Tommy never failed to be vocal in his disapproval of his relationship with Laurel. Ever since he'd begun dating Laurel in high school, Tommy had been against the relationship. Whenever Oliver asked him about it, he just waved a hand and muttered something about how he didn't think they were compatible. Counting on Tommy's disapproval was like counting on the sun to rise in the morning. Oliver just got used to it.

"I do. And I'm making an effort on that front, believe me. But nothing is going to happen between now and Tuesday, when I need to be at the cabin with a steady girlfriend in tow. That's why I asked Felicity."

Tommy's brow furrowed as he leaned over the table. "So you like Felicity now?"

"No! I mean, yes, I like her. She's my friend. That's why I asked her, because she won't make it weird. She knows we're just friends," Oliver explained.

"Does she?" Skepticism dripped off of Tommy's voice as he picked up his manhattan and took a long drink.

"Oh, come on. You've had lunch with us before. Tell me if you've ever seen anything there other than just friendship?"

"Oliver, I saw a very beautiful, very smart young woman who clearly cared about you. What's more, I saw my best friend who clearly cared about her as well. I think this whole plan of yours is a disaster waiting to happen. You're going to hurt her and you're going to hurt yourself."

Oliver scoffed. Of course they cared about one another; they were friends. What Tommy was suggesting was that he had feelings for her and she had feelings for him and… no. That was not happening.

"I disagree. I think this is the only way I can get through this holiday with my family without having to shackle myself to Helena Bertinelli."

"Well, I can appreciate the need to do that," Tommy agreed. He knew as well as Oliver did that Helena was a ticking time bomb of crazy. "I just wish I could witness the fallout of this terrible plan of yours because I'm sure it'll be the show of the season."

Oliver hummed as he took another drink of his Scotch. "Why don't you join us? You know we'd all love to have you and it'd get you away from your dad."

Tommy's eyebrows flew up. "What? Seriously, Ollie?"

"Yeah, why not? I'd love to have you there and you can keep me honest. I know Thea would be happy to have you too and my mom is so used to you hanging around I'm surprised she doesn't count you as one of her own children by now."

Tommy considered. He nodded slowly. "All right. I'll do it. Sure would beat hanging around Merlyn Manor, waiting for my father to find some new and interesting way to emotionally manipulate me." He barked out a humorless laugh and Oliver's heart went out for his best friend. He knew that Malcolm's treatment of Tommy and their relationship hurt his friend. He'd never been the best father but after Tommy's mother had been murdered by street thugs, it'd gotten so much worse. The two barely spoke anymore and when they did, there was always a confrontation.

"And you know we've got plenty of room at the cabin," Oliver mentioned, hoping to shift the subject away from Mr. Merlyn.

"I do remember all the raging parties we used to throw up there back in high school. Plenty of bedrooms for… well, I'm sure you recall."

A series of vivid images played back through Oliver's memory. Oh yes, he definitely did remember. In fact, there were a few times where Tommy and he had shared a woman at that cabin. The details were hazy in his memory, but he could recall everyone having a very good time. He chuckled.

"How could I ever forget?"

Just then, his cell phone buzzed in his pocket. He pulled it out and saw Felicity's picture on the screen. He hadn't expected to hear from her until tomorrow. He hoped the early response didn't mean she'd decided against helping him out. "Hang on, its Felicity. I have to take this."

"Go ahead, my friend." Tommy sat back, sipping at his drink and watching him.

Oliver answered the call. "Felicity?"

"Hey, Oliver." He couldn't read anything off her voice which drove him mad.

"Are you calling because—"

"Because I made a decision? Yes, I am."

He held his breath. "And?"

"Well, I've thought about it. Actually, it's all I've thought about. All day. Ever since you left my office, I've hardly been able to think about anything else. And I keep weighing the reasons to do it, which is chiefly to help you out, against all the reasons not to do it which is such a long list— Oliver, are you sure? Because I know you say this isn't a big deal and its just a little ruse but its also your family and I don't know how I feel about lying to your family even if you're okay with it and—"

"Felicity. Land your plane."

She blew out a breath, gusting in his ear. "I'll do it. I know I probably shouldn't and I'll almost surely regret this but… I'll do it."

Relief coursed through him and he couldn't fight the grin that stretched his lips. "Oh, thank god. Felicity, thank you. You have no idea how grateful I am."

"Oh, I think I do. You owe me that wine, mister. And pretty much anything else I can think up for the foreseeable future."

"How about we start with a little shopping spree?" he suggested.

"What?"

"We need to get you some clothes. You pointed out yourself that my mother might not buy our relationship with your current wardrobe."

"So… you're going to take me shopping?"

"Unless you'd rather go by yourself."

"And pay for this new wardrobe myself? Not likely," she scoffed. Oliver huffed a laugh. That was the Felicity he knew.

"That's what I thought. I'll pick you up tomorrow. Just text me your address."

"That's it? You're not asking if I have plans already for tomorrow?"

"Do you have plans tomorrow?" he asked.

"No, as a matter of fact, I don't," she replied primly.

"Great. I'll pick you up around 1pm then."

"Are you going to act this way on our cozy romantic Christmas vacation? Because I feel that's something I should know ahead of time."

"Goodbye, Felicity."

"Bye, Oliver."

He hung up, grin still plastered on his face. Tommy met his eye from across the table and shook his head knowingly.

"You are in such big trouble, my friend."