Disclaimer: Not mine. I wish.
This was inspired by Waiting for Superman by Daughtry, hence the title, and partially by the last episode, and is thus slightly spoilery.
Felicity Smoak is smart. She is better than smart and she knows it. She knows that she is good with computers. She knows that she is one of the very best at Queen Consolidated and that her skills are wasted as Oliver Queen's executive assistant. Regardless, she would not trade that for the world, nor her other position as part of Team Arrow. (She knew Oliver hated it when she called it that, but she did not care. He could use someone challenging him from time to time. It kept his ego from getting too big.)
There are times when she marvels at how her life has changed in the space of a year and change. She has gone from an underappreciated and underpaid computer tech at the depths of a huge company to being part of something bigger – something better.
Felicity's faith in Oliver never falters. Even when he makes poor choices. (One of the first that comes to mind is Isabel Rochev and the incident in Russia, as she has decided to term it.) Even when he lashes out. (The fiasco with Barry comes to mind then.) There is never a moment when she loses faith in him, regardless of how much it hurts.
When Oliver lashes out, it hurts. No matter how much she tells herself that he is not hers to keep, it still hurts. It hurts when she sees him going after other women, flitting from one to another like the (green) bumblebee he is. It hurts more when he tells her that he cannot be with someone he could truly care about. That makes her want to kick him.
Then her temper fades and she remembers that men like Oliver Queen do not date women like Felicity Smoak. They might be on the same team, but when the sun is up, Oliver Queen is the CEO of a multibillion dollar company. He is the son of Robert and Moira Queen. She is Felicity. Just Felicity. She is the tech who somehow managed to get a job that she was completely unqualified for. (She kicks butt at it anyway. Take that, Starling City tabloids. Felicity Smoak is good at her job. She did not get it because she was sleeping with her boss. She owns this job.)
She does not tell him that it hurts. It would be pointless. They have been dancing around each other for months and she knows it. She also knows that Oliver tries his hardest not to let anyone close. She might be his friend, but he will not tell her what sits in his chest and aches. She knows that he is probably more likely to say something to Diggle, even if he did acknowledge that they have been dancing around each other since they brought him back from the island after Tommy died. (They have probably been dancing around each other for longer than that, but she has been consciously doing it since he saved her from that land mine. The memory of a half-clothed Oliver swinging down from a tree on a vine to rescue her makes her cheeks heat and it is incredibly distracting. Though, perhaps, it might not be as distracting as his shoulders in his navy suit. Now that is distracting.)
Sometimes she imagines giving it all up and leaving Starling City, going off to Central City to be with Barry if he ever wakes up - like Oliver did after Tommy died. But that is all just a dream. No matter how much her heart aches, she could never leave. She loves Starling City. Oliver is making Starling a better place. He needs her – Felicity just has to keep reminding herself of that. (What Felicity cannot say is that she loves him. She is deeply, truly, irrevocably, and painfully in love with Oliver Queen and he does not even know.)
It kills her to see Oliver and Sara together. They have a history. She knows that. He also has a history with Laurel. He has a history with everyone. Everything is so ridiculously complicated that it makes Felicity's head spin when she tries to even think about Oliver's love life. (Sometimes she wonders if there will ever be someone in Oliver's life that does not have a ridiculously complicated connection to him. Somehow, that seems unlikely.) But it is not that Sara and Oliver are together that is bothering her. It is that suddenly, after being the brain behind the Arrow for so long, she is being replaced. She is jealous, though she will never admit it. (And part of her is jealous that he will rekindle his relationship with Sara when he told her that he could never be with someone he could truly care about and she can see incredibly clearly how much he cares about Sara.)
There is nothing Felicity can do. She cannot stem the pain; she cannot tear her feelings for him apart. (It's not love, she tells herself. She does not love Oliver Queen. That would be stupid and she is most definitely not stupid.)
(But if there is one thing she knows, it is that men like Oliver Queen do not date women like Felicity Smoak, and it kills her.)