There's a shadow behind Felicity's eyes when she shows up out of the blue after they haven't seen each other since he moved to Central City a year ago that Ray doesn't ask about. He doesn't pry when she asks where his first aid kit is and patches herself up, sewing a gash on her arm closed while sitting casually at his kitchen table like this sort of thing is an everyday occurrence. And maybe it is, for her. He doesn't ask why she's dressed from head to foot in dark purple and black, a hood shadowing her face, or about the black mask she holds dangling from her fingers when she walks in the door. He doesn't ask about the futuristic looking hovering devices that she refers to as "T spheres" with a strange sort of sorrow in her voice, or why her hair is black when the last time he saw her it had been blonde. He certainly never mentions the photograph of Oliver Queen she looks at whenever she thinks he won't see. A lot can change in a year. For Felicity, it seems a lot has.

The details come out on their own, eventually, after weeks of questions that Ray hasn't dared to ask have built up between them like a wall. Ray learns that Felicity is a vigilante- although, in truth, he could have figured that detail out on his own- but she tells him that she had actually been one for a while- almost five years, by her admission- just not in the traditional sense. He learns that Oliver Queen was the Green Arrow, another fact that should surprise him and yet feels right, somehow, and that he'd had a team that Felicity had been apart of, and that they'd all been picked off, one by one, by vigilante hunters employed by Damien Darhk, the mayor of Star City- someone named Sara Lance and her partner, whose name Felicity doesn't know- until only she remained. Ray can tell, from the tone of her voice when she talks about Oliver and her decision to honor his memory by carrying on his fight after he died, that Felicity was in love with him, but he doesn't ask her about that. Let her have that, he decides. Let that be the one thing she gets to keep hidden from this dark, cold world.

Sensing that a barrier has been lifted now, Ray asks her the questions he hadn't dared to before. He asks her what she calls herself, and she tells him, with that sorrow tinged smile that's become familiar, that it's Overwatch, and something about the way she says it leads Ray to suspect that she didn't give herself that codename. He asks her why she's in and out of his apartment at odd hours, and why she always enters and exits through the window instead of the door, and she explains that she needed somewhere to lie low between mission and patrols, a place to rest and recuperate and patch herself up if necessary, and she knew that Damien Darhk's vigilante hunters would never think to look for her in Central City, not when her home and her mission is Star City. He asks her, carefully because he suspects he already knows the answer, who it was that had trained her in more "traditional"(as she'd put it) vigilantism, and she tells him, again with that soft, sad smile, that it had been Oliver, at her own insistence, after Darhk's hired killers had whittled Team Arrow to just the two of them. She'd wanted to be out in the field beside him, to be able to fight back if something went wrong. She mentions, almost offhandedly, that she hadn't been with him when Sara Lance and her partner had finally caught up with him, that she'd been in the bunker, and though she never quite finishes that thought, it sounds like she blames herself for Oliver's demise. Ray's heart aches for her, but he doesn't know what sort of sympathy he can offer that would actually mean anything to her, so he stays silent.

Even with all the things that Ray learns about Felicity and her life, there's one thing he never quite manages to learn the details about. No matter how carefully he approaches it, now matter how gently he broaches the subject, Felicity refuses to talk about Oliver. Anytime Ray asks anything about him, she shuts down. She claims tiredness, or pretends not to hear him at all. On a few occasions, she even flees the apartment rather than answer his questions. It's clear that her memories of Oliver carry with them a lot of pain, and Ray feels bad for making her relive that pain, in any capacity. He stops asking about Oliver, stops asking anything at all about Felicity's life before the fall of Team Arrow. She's his friend, and he doesn't want to hurt her.

One day, Felicity stops coming to his apartment. It's weeks before Ray stops listening for the sound of his window sliding open and closed, or for the creak of her footsteps on the kitchen floor. He thinks at first that it's his fault that she doesn't come anymore, that maybe he probed a little too deep, or said the wrong thing, or asked one too many questions about Oliver, and drove her away. But then a month goes by without so much as a hint of her, without even one of the cursory messages she would send him from time to time, Ray comes to realize that she must have suffered the same fate as Oliver Queen and the rest of Team Arrow. Felicity Smoak, Overwatch, Ray's friend who had drifted in and out of his life recently like a Kevlar and leather clad ghost, had fallen to Damien Darhk's vigilante hunters. The thought fills Ray with sorrow. He hadn't realized how much he'd enjoyed seeing Felicity around, even as sparsely as he had, until the reality of never seeing his only friend again is staring him in the face. Ray doesn't know if he believes in an afterlife, and he'd never asked Felicity if she did, but if there is one, he hopes that in it Felicity is finally reunited with her friends and the man she loves.