The Villains Edition

Their friends weren't the only ones to witness Oliver and Felicity's connection. All were surprised by the petite blonde and her relationship with Oliver. In the villains case this meant that it was often not a pleasant surprise.

Helena was one of the first to personally encounter the pair in their early team days. The blonde she'd never seen before looked just as confused to see her in Verdant's basement as Helena was intrigued to see her. Oliver on the other hand was bluntly protective. He told the blonde, Felicity, to leave, so fast the poor woman probably got whiplash.
So she wasn't the only Girlfriend.
Helena thought Felicity be useful to her; Oliver probably manipulated her into sticking around to help him. Felicity was useful alright, Helena just didn't realise how much so.

She was set in her mission, she's lost Michael at the hands of her own father and she was going to make her father pay. Despite Oliver's high road rhetoric, she knew he wasn't on her side. She'd like to see what would happen if someone took his precious Laurel. But after he'd been so defensive over Felicity, Helena made her move. She was going to get her vengeance by any means necessary and that included taking prisoners. Felicity was most definitely useful to Helena. She was small and easily overcome but she made up for it, at arrow point in front of a computer. Felicity was a wiz and Helena now realised why Oliver kept her around. With Diggle and Felicity on his side, Oliver was able to end her crusade not to mentions the surprise added help from yet another vigilante girlfriend.
At least the guy was consistent.
After he had gotten his way and she was on her way to, she had a moment, they had a moment. He told her she wasn't alone. He didn't know she was already planning her escape. She was done with Starling, her mission finished for her. Maybe she would set up her own secret hideout. A vantage point somewhere high, she was The Huntress after all and maybe even with some IT support. She would never underestimate another techie again. Oliver didn't and his team was definitely better off with his. Helena could say she saw that first hand.

He didn't realise he was making the mistake of his life when he took her. The Count underestimated how much her life meant to Oliver. Everything clicked into place when he cornered her, Oliver Queen is The Hood and The Hood is Oliver Queen. Oliver was the one that locked him away, now The Count was going to get his own twisted justice. He toyed with her, strapped her to a chair in Oliver's office in the Queen Consolidated building and then circled her like a twitchy coyote. He called Oliver from her phone and relished in the shock that carried through in Oliver's silence. He cackled in delight as the vigilante's frustration increased by the second. He used Felicity as bait and Oliver didn't hesitate to bite. Ohh did he touch a nerve? Good.
While he waited, The Count had gotten acquainted with the lovely blonde shivering on the chair and his smile only grew with every shudder that ran through her as he twirled her hair around his finger. Her badge named her as Felicity; Felicity must have been something special to have Oliver running from his family. Running to her. She was unyielding, stubborn; she didn't speak a word aside from repeating that The Count had made a mistake and to let her go. Ha! Not likely. The Count had heard the tales of the less fatal tactics The Hood had been employing. If this was truly the case, The Count had nothing to fear. He'd already been imprisoned once and he'd break out just as easily if he found himself there again.
Oliver turned up quicker than The Count expected, but nonetheless he was ready for the vigilante. Still all menace even without his hood, like a typical bully. As a grand finale he cut Felicity's bonds and grabbed her to him. To see her pretty, pretty eyes glistening with pained tears and her beautiful skin raised, dotted with Goosebumps from the icy fear his drug created in her blood would be a beautiful sight.
The Count was wrong, The Hood wasn't using different tactics, he hadn't changed, he was just holding back. The last thing The Count ever did was threaten Felicity, Oliver made sure of it.

Isobel wanted QC, Oliver was a perk. He was around to save his worthless family name, but why was his glorified secretary so loyal to him and the company? All those short skirts, they sparked rumours around the office as to why Ms. Smoak all of a sudden jumped 18 floors from the computer basement to a desk in the CEO's office. They were vulgar and as a woman, Isobel almost took offence. Isobel had worked hard in a man's world to get to where she was and here was this woman being a complete stereotype. That's why she smirked the entire way through their exchange as she sauntered out of Oliver's hotel room that night in Russia. She proved Oliver's taste in women was much better that a simple secretary fling and the hurt she saw in Felicity's eyes only gave her that much more satisfaction.
Yet Felicity still stuck around. Even after Russia, she and Oliver seemed to only get closer. Felicity even attended his mother's funeral, Isobel knew there was no love lost between her and Moira but Felicity was crying. Huh, the tears were probably faked anyway. Isobel only realised their true connection when it literally hit her. In the form of Felicity hitting her with the van she was driving. Felicity had stepped up to save Diggle, clearly showing her dedication to the team Isobel had come to learn about. She's turned to Slade and relayed the high levels of trust she witnessed between Felicity and Oliver. He only waved her off, convinced that Laurel was the right target for his plan.
But Slade wasn't there that first day Oliver stepped into the board meeting at QC after the Glades' earthquake. The day masked gunmen burst into room threatening Oliver's life. Yet he did not save himself, he was held at gunpoint. Felicity was the one to save him. He returned the favour when he figured out there was only one means of escape. He sprinted over, caught her tightly around the middle and leapt straight out of a high rise window and saved the blonde. Himself.

"It's his fault I can't be with you. It's his fault I'm dead. It's all on him and yet you paid the price. Make him suffer!"
He went after Laurel, the woman in the picture his brother kept so close the nights they were together on the island. He would get his revenge. Oliver was the reason Shado was stolen from him. Now Slade was ready to return the same unkindness Oliver had once shown to him. She had been his plan till he saw Oliver with his Executive Assistant. She wasn't quite Oliver's type considering his history with Shado and the Canary. But Slade's belief that Laurel was truly who Oliver loved begun to waver. Instead evidence contrary to his belief had begun to mount in Felicity's favour. The Count was dead at Oliver's hand, despite the restraint Oliver had been showing previous targets because it was Felicity that was in danger. Isobel had been reporting the partner's inseparable trust. He even witnessed it himself when he set out to undermine Oliver's confidence by breaching the foundry setup. It was Felicity that Oliver immediately chose to protect. At the time he'd brushed it off as merely a reflex action on Oliver's behalf; because Felicity was closest to the danger, because Felicity couldn't physically defend herself, because the other two were more experienced when dealing with threats. Yet Oliver's actions had lodged themselves in Slade's side like a splinter. So he was glad that when Oliver walked straight into the Queen Mansion dragging a confused Felicity along that he had kept all his listening devices in place. It made sense that Oliver would love this woman, Slade saw the signs, and they had both learnt to keep emotion hidden on the island. Oliver had endangered Laurel and his family by showing affection, it would be logical to think that by the simple action of not showing her affection, he cared more for Felicity than many. Oliver was protecting her.

"Take one woman, take the other. It's all the same. It's his fault I'm dead. He is the reason we cannot be together. Why I cannot be there with you. Take them both. Destroy him."
Slade listens to her. He personally collects Felicity. She's small; he can barely feel her struggling. Later when Oliver stands before him, instead of the desperate reaction Slade was anticipating, he babbles about Slade not being able to truly see the strength in front of him.
Felicity is a surprise.
So is the needle that was sticking out of his neck.
Sara arrives to free Laurel and Oliver calls to the women, telling them to run. When Slade rids himself of the needle and looks to his brother he see's something different in his eyes. Felicity's success has given Oliver hope; Slade can see the fire burning larger and brighter in his eyes. Whatever feelings Oliver has for that woman, the most exposed are trust and pride. In that moment Slade realises he chosen the right woman to use as Oliver's pressure point but he'd made the wrong decision in thinking Oliver was protecting her. Felicity countered much of what Oliver was and in turn that made her perfect to play her role. Oliver was not protecting her; he had done the unthinkable. Yet Oliver had shown the ultimate amount of trust he had in Felicity and she had done the same for him.