As much as Team Arrow was Oliver found family, his biological and extended family, his biological and extended family was also involved in many aspects of his life. This is including his relationship with Felicity.
Walter Steele had the honor of being the one who first connected the two. Oliver's stepfather was the very catalyst for their first meeting. Walter, having met the blonde before, was able to see beyond her constant rambling through to her endearing intelligence and trustworthiness. He had entrusted her with a vital task of his own and she pulled through for him and more efficiently than he could have ever imagined. So when Oliver mentioned needing tech help, Walter did not hesitate to direct him to a Miss Felicity Smoak.
It had been a pleasant surprise to see her after he had been saved from his captors. Despite Felicity's unexpected presence, Oliver announced her as his friend. Walter quickly seconded his introduction He was touched by her visit, even though she made herself scarce, politely not wanting to intrude. Walter was a happy man to be back with his family and the chance to see friends once again.
It was just as pleasant, less of a surprise, when he saw her again at Oliver's side when he visited Queen Consolidated. Oliver had come to him personally and he was more than happy to make the trip to help, it was a smart enough move for the business he now heads up. Oliver had spoken to him beforehand about his plans for a slight restructuring in terms of positions, Walter however had debated that Felicity had shown more skill and talent than any EA could dream of. Still he was happy that when he saw that she was still be Oliver's side, the man needed someone to trust and her she was, stepping up to the plate. He couldn't have recommended a better woman for the job.
Of course his little blonde secretary was a step behind him everywhere; Moira thought she could see straight past her naive innocence into the heart of her 'opportunistic' ways. It was a surprise when she even followed Oliver before she held her position as a glorified secretary; she followed him right into Walter's recovery room. She was out of place but Moira held her peace when Oliver stepped up to her elbow, she watched the blonde intently after that.
She'd latched on to Oliver and by the looks of the ever rare but dazzling smile he mostly reserved for the secretary it seemed like her son was falling for it. Whether it was with or without his knowledge. She saw the looks the secretary would throw Oliver's way too, again whether anyone was watching or not. Longing stares and childlike moon eyes.
Felicity was intelligent however, sharp and shrewd enough to work out her secret. It only threw Moira for a moment when the young woman offered her a chance to come clean. However in the long run Moira, rather than see the appeal of honesty, was much easier to let anyone know she wasn't only keeping her own secrets but that she kept other's secrets also and especially when her relationships to her children were being threatened. The fact that she knew her son well enough to understand his pattern of eventually destroying his relationship with Felicity gave Moira the power that she needed to have the last word in that discussion. Things were cold between the two women after that. To her predicted outcome, her secret tore her and her son's relationship to shreds. Unpredictably, as she watched as an outsider, it seemed like he trusted Felicity even more now.
They visit Tommy's grave together when they get back from the island, after Slade has been dealt with. They stand silently side by side. They hold hands in a rare moment. Felicity brings flowers, she walks forward and places them by his tombstone and then returns. Oliver grasps her hand again. She says she never met Tommy but from Oliver's description he sounded like a great man and a good brother. She guesses that Tommy would be pretty proud. Oliver nods, swallows hard and remembers the words Tommy never said.
He's not a murder, he'll strive to be the hero and he's always going to try to fight back.
The decides she likes Felicity. She sees her coming and going through her club constantly. The woman is beautiful and stylish, perhaps falling a little short of graceful. A judgement she quickly reversed the first time she watches Felicity with a computer. She's different to the rest of the women who fling themselves toward her brother as he crosses the dance floor and past the bar. She walks in the skirting shadows of the bottom level of the club and heads directly for the exit. She's quite caring and thoughtful, it shows when she comes to Walter's bedside to welcome him back and Thea's happy that Oliver also recognises this as he gravitates to Felicity's side.
However the woman isn't afraid to stick it to Thea's brother. Thea loves it. Felicity Smoak is a force to contend with, Thea can tell from the way she raises her chin into an argument, despite the height difference Oliver has on her. She pokes him in the chest and throws up her hands in an exasperated gesture. Thea likes Felicity's fire. Meanwhile Oliver usually stands there and anyone that can make her brother look that deservedly sorry gets points in Thea's books.
Thea sees her talking to Roy a few times. But Thea's boyfriend refuses to say a word beyond "we've met before, she's around, she's really kind of nice". Though when she asks about Oliver and Felicity, a smirk creeps across her boyfriend's face and he says, "they're just playing catch up to what everybody else already knows". The he asks her "you know your brother pretty well, how long do you think it'll take him to make a move?"
When Thea asks why, she gets her answer and the promptly makes a deal with Roy. If he bets on her answer and wins, they split the winnings between them.
She didn't win that, but when she finally gets to know Felicity personally, after what feels like a lifetime in-between, Thea realises she didn't really lose either.
This took ages to figure out how to write, it's also probably the last one, till we get new characters I suppose. Cheers for reading.