There had been at least a dozen times since he willingly returned to the island that he could have told her how he really felt. Unfortunately, how he really felt varied drastically depending on the situation.
When he first met Felicity he was handing her a bullet ridden computer, fully prepared for the babbling blonde to pepper him with questions. Instead she looked him in the eyes and got to work. For weeks, she was his secret assistant in tracking down Starling City's criminals and she was none the wiser.
Then when he confronted his mother about her part in the Undertaking and she shot him, it was Felicity's car that he managed to reach. He could have called Diggle and honestly he had survived worse, but for some reason he sought out the assistance of the IT girl.
For countless operations afterwards he reprimanded himself for risking her safety, yet some part deep within him remained grateful for her continued presence. She was reluctant to join his mission, but when he brought Walter back alive he liked to think he gained her trust.
From that point forward he, Diggle, and Felicity operated smoothly as a team. Occasionally there were mishaps. Felicity worked best behind a computer and any time she ventured out it proved dangerous.
Until the night the Glades fell. As he tried to save the city, as he watched Tommy die, and as he prepared to face the accusations that would surely come from Laurel—he had to think about his favorite IT girl, huddled in front of her computer in the basement of a night club located in the heart of the Glades.
Days later he did what play-boy billionaire Oliver Queen does best—he ran. Back to the hell hole of an island he had tried so hard to escape for five years. He had failed his city, his best friend, and his family. The nightmares of the island were easier to handle than the burden of failure. Here, the only thought was survival.
Until, horror of all horrors, that blonde head came bobbing through the most dangerous island in the world. At first he thought he had been hallucinating. It wouldn't have been the first time. Her voice reached him in the trees and for just one moment he allowed himself to dream. Then he heard the click of the landmine and saw Diggle reach to disarm it.
From the exact moment his body lay carefully over hers—the closest proximity he had ever allowed himself to this delicate creature—he knew that when he went back things would be different. He vowed to be careful, to be diligent. He would protect her light and her goodness.
He would protect her.
Until he returned and realized that he couldn't lock her in a bubble. When the Dollmaker grabbed her off the streets, his first reaction was to rip the man limb from limb. His second reaction was to shout at Felicity until she understood how ridiculous he thought her part in this mission was in the first place.
Then when they went to Russia to retrieve Diggle's ex-wife and he watched Felicity's damaged expression as he walked out of Isabel's hotel room he nearly threw himself at her feet and begged her forgiveness. He hadn't realized that he had been actually expressing any of the thoughts that had been plaguing his dreams and his stomach fluttered with hope that possibly Felicity felt the same. Then later in his office when he tried to hint that she was the one he could truly care for, her one concern, as always, was for him and what he deserved. He locked any possible feelings away under the disguise of protecting her and with the knowledge that, although he wasn't sure exactly what he deserved, he knew it wasn't her.
All of those emotions surfaced though when her blue eyes stared crystal clear into his, begging him not to take another life for her sake. After Tommy's death, his first instinct was no longer kill or be killed. His survival, if he was honest with himself, was a matter of indifference. But when the Count held the dual vials to Felicity's throat, the matter of her survival was of first importance. Without thought and without regret three arrows found their target. He seriously considered telling her that night how he felt because it had come into such clear focus mere hours before. She was already at risk because of her association with him and he was selfish enough to want to benefit. Yet when he realized she felt guilty for his actions he crushed his feelings deeper inside once again.
He tried to stay away, to keep his distance, but the clear boundaries of friendship had, at some point, blurred, and he found himself touching her, reaching for her and reassuring himself that she was still there.
And then Barry Freaking Allen came bouncing into Queen's Applied Sciences lab and started talking Greek. Oliver knew that there was something off about his story and as if that wasn't bad enough, Felicity jumped right in as if she and Barry were old friends. And the way he looked at her…
Now Felicity was back from Central City and Oliver couldn't help but think that he had jinxed her. Barry made her happy. The light that Oliver had been slowly stealing from her eyes these last few months Barry had somehow replaced. Oliver couldn't begrudge her that. Except he had and now Barry lay in a coma and Felicity sat in the Arrow cave, stoically looking at her computer.
He would make this right.
"I'm sorry," he stated, afraid to look away from the weapons that gave him strength.
"Are you apologizing to me, or were you talking to your quiver?" Felicity snapped.
He smirked. She wasn't going to make this easy on him, she never did.