This was something I planned to write before 3x19/3x20 when we found out what pushed Oliver to join the league, but I didn't get a chance to write this then. I also wanted to write this type of fic (I've also been writing more now so some of my ideas from previous seasons are finally materializing) I'm a bit late to the party so apologies if this was done before. I was also trying to get in Oliver's head space when he made some decisions.
Still don't own anything and this is not beta'd. Let me know what you think.
1
He would have chosen her during the night of the Undertaking, but the threat of a massive destruction was looming. He tried to get her out before everything went to hell, but she stood her ground. "If you're not leaving, I'm not leaving" is her response and in the end, he let her stay and help him save the city.
He thought it was over, but they find out there was another device. Damn Merlyn. He would have gone to her then, but the knowledge that the device is near CNRI kept him from doing so. He asked if she was okay and then rushed to the woman he thought still held his heart. The devastation was immense although nothing prepared him for the sight of his best friend impaled by a rebar, eventually succumbing to his injuries.
He would have chosen her after the fallout, but the feeling of fear, defeat, and desolation won over - so he fled. His time alone doesn't last long because as he will soon realize, she will always come for him. Her being his anchor and beacon of light will be a pattern.
2
He would have chosen her in Russia, but they were in hostile territory with unexpected and unfriendly company. They said keep your friends close and your enemies closer, and he did just that. Maybe more. What started as a simple conversation to perhaps gain a bit more insight on his cold brunette rival led to a moment of weakness.
Even in his transgression, he couldn't help but think of her. He hoped that it was something that could be swept under the rug and kept in Russia, but that flew out the window the moment he opened the door with her telling him "It's time". And of course, it was the exact moment that their rival slithers out of his room with her dress unzipped while giving her a look of pure condescension. He could tell it hurt her because of all the women he could choose to play around with, he had to pick the one who looked down on her and treated her miserably.
After the mission and a tense trip back home, they tried to act normally. Things were tense. Feelings have shifted. He had to put a kibosh on anything progressing by letting her know "Because of the life I lead, I just think that it's better to not be with someone I could really care about".
He would have chosen her then, but he believed he doesn't deserve her. She was quick to tell him that she thinks he deserved better, as she always will.
3
He would have chosen her after he confronted his Mother, but he was too raw with her revelation of yet another one of his Mother's secrets. He found a familiar face and body who was hurting too. He figured it made sense to try a relationship with someone from his past who already knew what he went through as well as his secret. Perhaps gain some closure in the process. What he didn't know was that his words from weeks ago would hunt her. It was a rejection and a hole in a dam of pain she hid very well. Had he known that his Mother threatened that she will lose him, he would have reconsidered his actions. Hindsight was never kind to him.
For a long time, he fought to rid himself of his Lance-related blind spot only for it to be replaced with another. The blind spot eventually disappeared though it didn't leave everything unscathed. If he knew his actions caused issues of hurt and insecurities to bubble up from within her, he would've done things differently - anything that would have prevented her from getting shot by the villain that got under her skin. He was amused that she didn't have scars, but now that she has one, it unsettled him. He vows that as long as he lives, the one on her shoulder will be the only scar she will bear - if only the heavens heard his vow.
He knew would have chosen her then, but he didn't want to tarnish the light inside her. He wasn't ready yet. Too bad that when he starts to think there is a chance, she was starting to realize that maybe they were unthinkable.
4
He would have chosen her beyond their first date, but fate had other plans. Their date would have been the beginning of something special, but they got blown up. Her bloody and unconscious form is something he doesn't want to see ever again. He is convinced this was his fault. If she was conscious, she would have backed Diggle up and let him know it wasn't. To him, this was his fault because his two personas cannot coexist, and probably will never coexist. It's cruel to come to this realization as you see the life you wish to have right in front of you – the woman you love gazing with pure adoration at a newborn; even crueler when this unraveled as he finally acknowledges that he loves her. They should be celebrating with their teammate on the new addition to their family, instead they both had their hearts broken.
The stakes were too high to put Oliver Queen before The Arrow. What he doesn't understand was that it didn't matter to her if he was Oliver Queen or The Arrow. She loves him full stop. His team would have helped him figure out how to be both, but he decided already. He would have chosen her then, but first he needed to really find and know himself. He watched her walk away, unable to hide her tears and broken heart.
5
He would have chosen her when he came back from what everyone believed was his death, but he became a pawn in a diabolical man's plan to overthrow The Demon's Head. Everything that could have gone wrong since their date went wrong – their friend died, his sister was used by her father to kill said friend, tensions and the distance rose between the two of them, and he left for a duel with the demon himself.
She tried moving on, but how could she when their pull is so strong. She wasn't asking for anything else – just him. Her belief in him was strong, as it always was. Her joy and relief at seeing him alive was short-lived. She was always one of his biggest, if not his biggest champion until he mentioned that he was working alongside the very man who put them in the circumstance they found themselves in – the one who orchestrated this mess, The Magician. Suddenly, her belief in him was fractured because he chose to trust the enemy than his team, the ones who always had his back. In hindsight, he should have gone to his team. He would have chosen her then, but he made a snap decision and his back was against the wall.
*the one time he does*
It took a while, but they eventually rebuild the trust that was shattered that night in the alley. They came to a truce. He had to accept that she must move on, even though she couldn't. She had to accept that they had to play the cards they were dealt with – even if it meant teaming up with a mass-murderer. Both hoped that this difficult road they are in would lead to each other in the end. Nothing worthwhile ever comes easy.
He thought his back was against the wall then, but he would later be a desperate man making a deal with the devil himself - for her.
They agreed to meet that night at The Foundry. It's not unusual for her to be the first one to arrive. What was unusual was a man dressed in dark clothing, slicked back hair standing in front of her – The Demon's Head. After she used her loud voice emphatically telling him that Oliver will never join him, he tells her that he will beg him after he gives him a motivation to join The League. What happened after was a blur to her and something that he later cannot bring himself to watch from The Foundry's security cameras. She fought back as much as she could but she was up against the leader of the League of Assassins. She was able to kick and punch and eventually get a few scratches in. She ended up getting stabbed in the abdomen, with a sword that was eerily similar to the one he used on Oliver, telling her a life for a life, and then he left.
He arrives and sees the mess from the stairs - glass everywhere, clear signs of a struggle and he leaps the last few steps. He calls for her, for Diggle. He is terrified and hoped none of his team mates are hurt. He hears her whimper and he felt his chest tighten. She's on her side, blood pooling around her. He tells her to stay with him. He isn't one to beg, but he would grovel and even burn the world down for her. She was always the exception.
He desperately stops the bleeding, asks her to keep her eyes open while he finds a way to call for help. He yells at the top of his lungs for somebody, anybody to help them. It's useless. Neither of their phones is in sight and he knows, they both know, that if he leaves her side it might be over – forever. So he makes his choice then and chooses her. He puts pressure on the wound as he says her name like a prayer "Felicity". He cannot wait for help to arrive. He apologizes for the pain that she will endure as he grabs a phone, carries her to the exit and calls for an ambulance. He pleads with her to hang on. She just needs to hang on and he'll fight whatever he needs to fight for both of them. He is done leaving her. He tells her that after this is over, he'll make their dreams come true. He tells her that they will drive into the sunset and leave anything behind as long as she holds on. He apologizes for those times he could have chosen her, but didn't.
Her shallow breaths and her assurance that everything will be alright didn't help. How could he be alright if she was fading away? She touches his cheek, says his name the way only she can "Oliver" and tells him she loves him and she doesn't regret anything and neither should he. He tells her that she isn't allowed to leave him and presses a kiss to her forehead. He hears the faint sounds of the ambulance and assures her that help is coming and that they will fix her. He yells at the paramedics as they come into view and he feels her hand go limp. If Felicity Smoak dies, Oliver Queen dies with her, because he chooses her.
As he watches the paramedics revive her from his corner in the ambulance, he thinks back to the perfect time at the lair after they decided to stick around and review meeting notes to get his family's company back. They were working on strategies over Italian takeout to reclaim Queen Consolidated and despite the seriousness of the matter at hand, they were smiling. They were teasing over a bed she bought him. He teased her about not bringing him coffee. He apologized numerous times for the employment situation she was in, but she waved him off with a smile, letting him know things will work out and that she'd be where she was needed. It was a night that made him feel that as long as they had each other, things will be okay. He should have chosen her then.