Another analysis of the infamous conversation in 2x06. I'm doing this in two parts. First from Felicity's perspective and the other from Oliver's perspective.
Isabel Rochev made perfect sense. Isabel was cold, calculating and everything that she did had an agenda. Maybe it was a woman thing. Maybe it was a high achiever thing. Felicity understood her and more specifically, she understood what Isabel could gain by sleeping with Oliver. Felicity knew that Isabel and a sizable amount of Queen Consolidated staff thought that she was sleeping with Oliver, even some of her old co-workers in I.T.
Isabel's not-so-subtle sizing up of Felicity had not gone unnoticed and, being that Isabel was a woman who was used to getting her way, it had to drive her crazy to see that Felicity seemed to get Oliver's attention when no one else could. To Isabel, this was a game, making Oliver almost inconsequential. Oliver was the prize. After everything that Felicity and Oliver had gone through, it was almost funny that Isabel thought she could destroy Oliver and Felicity's relationship by sleeping with him. If Isabel's goal was to still control Queen Consolidated and if she thought she could manipulate the CEO through sex, like she thought Felicity did, Felicity couldn't blame Isabel for trying. It made sense, in a cold, ruthless business bitch of the year kind of way, but it made sense.
Oliver, on the other hand... Oliver…It was like her mind was running on an internal feedback loop. Whenever her mind wasn't occupied with her work, the short film of Isabel Rochev sliding out of Oliver's hotel room like a snake kept playing back in her head. No matter how many times it played in her mind, his actions still didn't make sense. Oliver knew that Isabel Rochev was on the old "list" and while not everyone on the list deserved an arrow in the chest, that fact that she was on the list made her at minimum untrustworthy and at worst Lady Macbeth. She had been hell-bent on taking over Queen Consolidated, undermined Oliver at nearly every turn and was just a bitch to Felicity. She was the enemy and, in the office, just like in the Arrow Cave, she and Oliver were a team. So why, on G-d's green earth, would Oliver, knowing the danger she posed to his family, his livelihood and to his business, take her to bed? It didn't make sense.
Felicity wrestled with this question for days after they returned from Russia until, when Oliver asked her to deliver a set of papers to Isabel's office, she finally broke down and asked her burning question.
"Why her?" Felicity asked, stopping Oliver mid-stride. He turned to her with a slightly exaggerated turn, like he had been expecting and hoping to avoid this question. Still, he walked back to her desk and allowed her to finish, "I mean besides the obvious leggy model reason."
"It just kinda happened," Oliver replied almost automatically, "It didn't mean anything."
Felicity hung her head. That makes it worse, Oliver, reprimanded Felicity in her head. Sometimes, it was like Oliver forgot whom he was talking to. She was not Laurel. She wasn't Sara. She wasn't any of his girlfriends or flings that could be satisfied with a smile and superficial answers. She was Felicity, his friend, his colleague and most importantly see-through-er his bullshit. Oliver's words fell from him lips so automatically that Felicity couldn't help, but wonder how many times Laurel heard the same excuses. It was sad. She thought that by now, after everything they had gone through, that Oliver would know better than to lump her in with all of the other non-familial women in his life. She was special. Wasn't she?
"Hey," Oliver said suddenly in a softer tone.
It was the tone that caught her attention. Oliver had always been the master of multiple faces. He was the son, the playboy, the warrior, the brother, the lone wolf trying to be a leader, but every since Tommy died, he's tried something else. He's tried to be better friend to both her and Diggle. For all of the "sleeping with Isabel" crap, she was proud of him for taking the chance and helping out John when he needed it. She thought she heard "Oliver, the true friend" in that tone, and that's what made her look up.
His face was different. His expression was more open and raw. Felicity didn't know what she was about to hear, but she knew it would be something more than what "Playboy Oliver" had just offered her.
"Because of the life I lead…" he started, taking time with his words, "I just think that it's better to not…be with someone I could really care about."
Somehow, that was an arrow to the heart that she wasn't quite expecting. In that one, slowly crafted, carefully worded sentence, Oliver produced so many emotions that she literally didn't know how to process it all. She had to get away from him before she did something embarrassing. It seemed that her heart had installed a temporary verbal filter because somehow she managed to stay quiet as she gathered the things that need to deliver to Isabel's office. Stuffing her own feelings in a box so that she could organize, categorize and possibly cry them out later, she replayed the sentence in her head, analyzing it "Friend Felicity" as opposed to "Felicity, girl with a crush", as she walked by Oliver. As a friend, she heard something different in his sentence. She heard Oliver's loneliness, she heard his fear and she heard that he still believes that he deserves to be punished. With everything that has happened, he's still trying to achieve redemption in his own eyes.
Felicity turned her heel and wasn't surprised to see Oliver had turned to face her. "Friend Felicity" has something to say and even though Oliver didn't give her the answer she wanted, he had tried. He had tried to lay something bare on the table and "Friend Felicity" felt the need to honor that.
"Well, I think…I think you deserve better than her," Felicity said, giving voice to the dignity of their friendship instead of her personal pain. She turned and walked away, trying to leave Oliver behind in more ways than one.
Next up: The same scene, but from Oliver's perspective. Remember, Oliver is really good at pretending that he is an idiot, and sometimes he actually is.