A/N:This didn't fit into any of the categories for the other Arrow fic I have, which is the only reason I am doing this as a one shot and on its own. Now, I realize that timeline-wise, this is going to get a bit out of order. Also, I am highly aware that Felicity is seeing Billy for what is probably the majority of his [Oliver's] time in office. Regardless, this will be when he's mayor and not when he's still campaigning. Also, may I just point out that while I don't condone cheating in any way (which will be addressed), it's not like Oliver didn't try and face up to his mistakes; and yet all people do is criticize him. Sure, he screwed up, but he's been constantly trying to deal with it, and it's not like Felicity is the pure hearted angel that everyone wishes to constantly cast her as. If you Google stories, it's always 'Oliver hurts Felicity' or 'Oliver cheats on Felicity'. Excuse me? Am I wrong in remembering that she's lied to him on at least three separate occasions? At least. All right, rant over. I just had to get that off my chest after constantly hearing how awesome the pairing is. No. Just...no.

Spoilers ahead...obviously. x_x

The Breakup, AKA Oliver Takes Back His Spine

Oliver sighed as the day finally caught up with him. He was tired of people like the Damien Darhks of the world, who thought that they could dictate how things ran in his life and in his city. He wasn't going to put up with it any longer, and he knew that meant putting William at a distance. Rubbing his eyes tiredly, he thought back on all of the complete awkwardness, tension and hurt that had been in the atmosphere lately. It was his fault completely, there was no denying that. It all stemmed from his cheating on Laurel,and not just with Sara, but also Samantha. It was a wonder that the Lance family wanted anything to do with him after all he had done to them. He had just learned to withhold a flinch every time he saw one of them out of guilt and now all of this happens. Laughing bitterly in a somewhat bitter and humorless way, he recalled trying to adamantly persuade Captain Lance that he was a changed man now. Maybe he had changed, but the fact that he still hurt people hadn't changed at all. He knows that there are several people that have called him a monster and a murderer to his face and even behind his back. He wasn't so naive as to think that even those closest to him, including his fiance and friends, thought he was a killer. He might have at one time flinched at those remarks, but he'd been forced to become almost apathetic over the years. It wasn't until he'd decided to get closer to people and let her start to make so many changes in his life that things got so complicated. True, he had started to not kill after Tommy had died, but letting Felicity stay past Walter's return like their original agreement was a mistake. He saw that now.

He frowned at that, putting his now aching head on the table and closing his eyes for a moment. He wasn't about to fall asleep, but he needed to attempt a moment of meditation to think. He wasn't so stupid as to not have Felicity checked out before he had even been forced to get into her car that one fateful night after his mother had shot him. He knew that she always tended to act like she could do no wrong and he had foolishly just played along with it. He knew all about her lies and secrets, which admittedly sounded pretty hypocritical of him obviously. Things between them were starting to reach a boiling point, and couples that had all the secrets like they did weren't meant to last for long. Upon hearing Felicity's approach, he inwardly sighed and sat up. He knew what this was all about, and while a part of him dreaded the conversation; another slightly sadistic part was looking forward to it. He had no shortage of things to get off of his chest, and by the looks of it, neither did she. Their relationship was over and both of them knew it. He kept his face neutral, even if he knew that she hated it when she couldn't tell what he was feeling when he did that. She kept her distance, metaphorically and physically, obviously bracing herself for what she was about to do. He already knew what she was about to do, although her leg twitching was unexpected.

"Oliver, we need to talk." she started, keeping her distance as best she could.

"About a number of things, I would guess." Oliver casually responded, not expanding on his previous thoughts. He watched in slight detachment as she came a little closer and took off her engagement ring. He couldn't say that he was necessarily surprised, but watched nonetheless as she put it on the table and backed up slightly.

"I know the position that Samantha put you in, and I understand that it was an impossible decision. You should have told me." Pausing for what he suspected was dramatic effect, she continued her assault. "And now, you're sending William away; but once again, you have left me out of the decision." Oliver started counting in his head to calm down, because inside his head he was not happy at all. Things had gone from a simmer to a boiling point, which was almost funny considering the person in front of him had almost no cooking skills whatsoever.

"Felicity-" he broke himself off in shock, as he saw her legs twitch a bit. Obviously the chip was starting to work, which meant he had precious little time to work with before she got up and left. Sure, he'd be happy she could walk, but he needed her to wake up. He saw her try to move her legs and moved in front of her to stop her from attempting to leave. As...grateful as he would be for this toxic relationship to finally be at its end, he needed to make his own thoughts known. She looked up at him, with an expression stuck somewhere between shock and indignant. She always did like having the last word, but he wasn't about to let her having it this time.

"Oliver, let go." she told him, scowling at him. He backed up a bit, just to see her try again and gave her a flat look that said 'sit down and shut up for once in your life'. She acquiesced, and reluctantly sat there.

"No, you don't get to throw a fit like that and then storm out of here like a five year old child, Felicity." he told her flatly, emphasizing her name and making her flinch at the obvious slight.

She opened her mouth, but quickly closed it, knowing that it would make little difference anyway. Besides, she'd spoken her mind. He should be allowed the same, although she'd heard him let loose before and she was not looking forward to the diatribe she was about to face. She swallowed as she looked at the expression that he usually gave people that he tried to distance himself from. She tried not to avert her eyes and was only partially successful.

"Felicity, I will grant you the fact that my past has come back to haunt me several times. I've tried my best to overcome it and deal with it; but to be honest, its none of your business. Yes, I had a deal with Samantha that had nothing to do with you. At first, I felt sort of guilty for not telling you. But now that I've thought about it, I have come to realize that it was my son and my deal I made with her. You should have never done what you did, putting Barry in such a hard place when we already had so much to deal with. While I understand that you wanted to know what was going on with me, it was personal and confidential and you had no place cornering him like that. You used his weakness, his inability to come in between people and grabbed the test from him. And while I probably would have sent them both away regardless, you had no right not only interfering, but using him like he was just a some...tool to be used and thrown away. I know he's too nice to be angry with you and has already forgiven you, but that doesn't mean I've forgotten.

Oliver sighed, taking a breath. The next few things he had to say probably frustrated him the most.

You have been acting like you have some sort of moral high ground when it comes to how I deal with things, especially regarding William. Well, I'm sorry if I didn't tell you that I was sending my own son into hiding and making sure that he was safe from psychos like Darhk. I wasn't about to waste time asking for your opinion when I have had to deal with making sure that he was safe again. So, yes, I did it without asking and I'd do it again."

"Oliver, you can't possibly-" Felicity started, but was stopped when he raised his hand.

"I'm not done, Felicity." he interrupted, halting her mid sentence. "I have to wonder, just how many lies of your own you've told me?" At her indignant expression, which was an obvious state of denial, he gave her an 'oh really?' look.

"I've never lied to-"

"But you have, and it wasn't even only me that you lied to!" he yelled, turning to the table and slamming one of his hands down on it, making her flinch. "You lied to me when we were in Ivy Town, and several other places. And do you think I'm blind, not noticing you flirting with Billy Malone when you think I'm not looking?

She looked alarmed, not expecting him to notice, let alone know who he was.

Yes, I know who he is, which means that I had Thea do a background check on him. I won't ruin his career for your misdeeds, even if he shouldn't be messing with people that are in an established relationship."

At this, she gave him what seemed to be a distinctly sarcastic look, which he knew the clear meaning of. You're one to talk.

"Yeah, I know I'm not exactly the best example of someone who has had the best past or even current ability to hold relationships. I don't think I can, and maybe Laurel knew that; maybe she didn't." he thought out loud. "Anyway, aside from that, exactly how long after I went to Ra's did you run into the safety of another billionaire? You sure seem to like to try and "fix" people and then leave when it's convenient."

Felicity looked at him like she had just been slapped, not quite believing what she had just heard.

"That's not fair. I spent weeks believing that you were dead."

"And yet you kept it a secret until I walked in on you two. Obviously you weren't that broken up about it." Oliver kept his tirade going before she could say anything. "I won't deal with it anymore. I've put up with you not trusting me and following my orders when we're doing Arrow business. You've only made things worse and it can't go on any longer. From now on, unless I need your help, I don't want to see you. Period."

Felicity blinked, as if she was expecting some more and tried to get up again. She almost expected to see him stop her again, but he merely walked away and ignored her, She tried to avoid the stabbing feeling that accompanied not only all that he had said, but that he was acting that she wasn't even there. Trying to act like it didn't bother her, she slowly got up and left with the little dignity she had left. Little did she know, this nightmare wasn't exactly over.

Thea had intended on coming over to deal with what was going to a clear backlash, in one way or another. She hadn't been sure why her brother had wanted her to suddenly look into what had seemed to her like some everyday cop, but now that she knew, she was tempted to use him as arrow practice. It wasn't entirely his fault, seeing as her brother's thankfully former fiance had used her womanly wiles against him. She heard her opening the door and decided to hide in the shadows for now. She needed to deal with this possibly political mess before going after Felicity. She waited a few minutes before opening the door to the loft and looked at what seemed to be a brooding Ollie. She wasn't sure whether to question him or congratulate him, so she just waited for him to acknowledge her presence. While she could sometimes barely tolerate his overprotective ways, he was always happy to see her. Sometimes, that in itself irritated her. She wanted him to let his guard down and actually feel something around her for once. Maybe it was an older sibling thing. Finally, he went to the coffee maker and started it, getting two mugs. She'd never know how he did that. Even practicing so much at being wary of her surroundings as she had, she'd never been as good as he was. Without turning around, he set the mugs on the counter and got out some much needed comfort food and finally acknowledged her.

"Thea, what are you standing there for?" he asked, turning around with a small smile and a tired look on his face.

She knew that he hardly slept, especially with all of the stress lately, but he looked exhausted. She supposed that if she pretended not to notice and made him relax with her on the couch, he might at least take a nap for a while. The politics could wait until they were at the office tomorrow. She approached him casually and tried not to be too casual at the same time. Her brother could read emotions and body language incredibly well, especially hers. Leaning across from him against the counter, she tilted her head a bit a hummed.

"Well, I noticed that you seemed pretty deep in brooding mode and decided not to interrupt. Besides, spooking you would do me little good," she said, cringing and trying not to facepalm as she saw him flinch. Sometimes she just couldn't shut up. "Don't do that, Ollie. You know that I wouldn't care. I can fight back if something happens, you know."

As she saw him nod and avert his eyes, she could tell that he was about to return to his previous state and saw fit to stop it in its tracks. Biting her lip, she figured this would turn out pretty well or extremely bad for the both of them. Taking a deep breath and releasing it, she took a stab in the dark, metaphorically speaking. At his questioning gaze, she opened her mouth to say something and closed it. She wasn't exactly sure what to say. Oliver turned back to the coffee and poured both of them a mug, before walking over to the couch, She brought the cookies and they both sat down, enjoying the silence for a while before he gave her the patented big brother 'spill it' look she both loved and hated. Grabbing a cookie to stall, she thought about what to say and decided to be the sister she usually was.

"I was walking here and saw Felicity leaving, and walking no less. She looked less than her usual chipper self."

Oliver snorted, which for some reason sounded both bitter and sarcastic at once.

"Be honest, Thea. How long were you eavesdropping?"

"I wasn't-" Thea tried defending herself before looking at her brother's 'oh, really?' look. "Okay, fine. I was listening in, but I wasn't there for that long."

Her brother continued giving her the look and she pouted, crossing her arms. He rolled his eyes good naturedly.

"How old are you? Three?" he asked her, shaking his head.

She stopped pouting when she saw that he was smiling. She was fine with him thinking she was being a three year old if he would smile. She returned the smile and patted him on the cheek.

"Funny. I distinctly remember you admitting that you've never been that mature." she shot back, now giving him a smirk. He raised his hands in surrender, giving up and obviously now believing that she hadn't been there that long. "So, what's this mean? Are you back to being the city's most eligible bachelor?" she asked him, grabbing the blanket off the couch and covering the both of them.

Oliver raised his eyebrows at the action and rolled his eyes as his sister cuddled up to him. Sometimes Thea could be about as subtle as the quietest assassin. This was not one of those times. She had obviously noticed the toll the day had taken on him and his recent lack of sleep, but was letting him keep his pride intact. While he was thankful for this, she could be exasperating at times. Yeah, like he was any better when it came to her and being the overprotective big brother. He sighed and leaned back; letting her lean on him, while getting comfortable. She poked him, demanding an answer to her question. He looked at her, slightly amused. It was just like her to be the one demanding that he forget about his worries, at least temporarily.

"I don't know, I guess I am. I suppose I'm just glad to be out of the relationship, you know? It was too toxic and it just couldn't go on." he said ruefully. He started a bit as his sister gave him a sympathetic look and rubbed his arm. They continued to talk for a while longer before eventually falling asleep together on the couch. She had watched him fall asleep first, which was almost surprising. Usually he would force himself to stay awake, so that he could make sure that she had fallen asleep and was safe. She supposed that what with mayor business, and then this whole thing with Felicity and William; he'd finally crashed. Eventually, she fell asleep, laying her head on top of his shoulder. She'd deal with his ex in the morning, no doubts about it.

Surprising her yet again, Oliver managed to sleep in for several hours afterward and not just a nap like she had expected. She was tempted to try and drug his coffee while he wasn't looking but not only would he probably sense it, he'd undoubtedly be pretty mad at her for a while. It didn't mean that she hadn't wanted to try it. A few people had succeeded, even his former fiance. She was getting ready to leave and probably later ask to move back in with him later when he'd actually rested. She was almost to the door when she heard a groggy Ollie call after her. She almost wanted to lie like she used to and tell him that she was going to meet a friend or something, but he had been lied to enough. She walked back over to him and made him lie back down, deaf to his protests that he'd slept plenty.

"You look like crap, Ollie. There's been a lot going on lately and you need to relax while things are slow. I don't care if you take the whole day off to sleep, but I'll keep coming over to make sure you're getting your sleep. At his sleepy and yet questioning look, she shook her head. "We'll talk about it later. Just go back to sleep."

Finally, he sighed and grabbed her hand to comfort her, but him as well. She wasn't going to leave him. Giving him a goodbye kiss on his forehead, she made sure he was comfortable and walked out the door before heading to her place to get ready for her day at the office.

It was really quite unfortunate for Felicity that she decided to go and try to get some things from Oliver's office. She had only been let in because she was typically around the mayor and had even been around during his campaign. Naturally, the news of the breaking of their engagement wasn't exactly public knowledge yet. She decided that she had to use this to her advantage while she still could. And while she really was quite shocked that Oliver wasn't here yet, she wasn't going to waste a moment. Her plan had been going brilliantly until she felt something sharp against her neck and heard one of the voices she dreaded the most. She had no doubt that Oliver had told his sister what had happened, if the ice cold tone that followed and knife against her neck said anything.

"What are you doing in my brother's office?" Thea asked, trying hard to sound civil with the woman. Felicity stupidly decided it was best to play dumb, just in case.

"It's just me, Thea. I'm here all of the time." she responded, trying to keep her own tone light and unafraid of her ex's sister.

"Do not play me for some fool. I know that you guys are no longer engaged, which means you are no longer allowed in here without his permission. You can no longer come and go as you please. He shouldn't have allowed you in the first place. It's good to see that my brother finally regained his backbone that you stole from him. Go back to Malone, just make sure it's not here. You're no longer allowed here unless you're escorted by security, and don't even think about hacking the system. Now leave before I force you, because you won't like how I do it." Thea said, narrowing her eyes. She took the knife away, just enough to let her stand and shoved her towards the nearest security guard. "Make sure she never returns without the Mayor's permission."

He looked confused for a moment, but escorted her out nonetheless. Thea saw them walk away and stopped them. Before you go, I want you to leave my brother alone or else Felicity."

In the meantime, Thea had some work to do. On her list was making sure that everyone knew to leave her brother alone to rest for once. She didn't care who she had to threaten or talk to. He needed some sleep and she was going to make sure he got it. He had always taken care of her as her big brother and now it was her turn.

A/N: Meh. I know I majorly came down on Felicity, but honestly, she should have remained at Queen Consolidated or some other IT job as a consultant for the team. As a friend or even confidant, she's fine for Oliver, but as a love interest? I say no. Too many things are wrong that are just shoved to the side for convenience's sake. It should have been Nyssa or Sara, maybe even Laurel as a last shot.