I'd want them to cement their friendship first. I think on-screen relationships (mostly) work better if there's something definitely there between the characters first, even if it's antagonistic. As it said in the article you just linked in another post, the audience needs something to build their expectations on, whether it's passionately adversarial or solid camaraderie.
I think I'd like to see Oliver make a genuine effort to get to know Felicity beyond their existing as work colleagues and partners in crime. He likes being around her; genuinely enjoying her company and being able to relax in a way he can't around other people, because she knows who he is and he doesn't have to make excuses all the time. He would serve as an audience surrogate for the viewers to get to know Felicity better - something we all want - with the added benefit of seeing a more open and vulnerable side of Oliver.
Diggle has other relationships in his life - his nephew, Lyla, old army buddies - but Felicity doesn't have any that we're aware of, so it would be perfectly natural for Dig to be off somewhere having a personal life, leaving the other two thirds of the team alone together. And they have to eat, right? I can easily imagine Felicity saying she'd like to try such and such type of cuisine, but she's never gotten around to it, and Oliver dragging her off to try it. It would be an easy habit for them to fall into, and Oliver would keep doing it because he enjoys her company and he gets a kick out of her reactions when she tries new things.
With the understanding of how little experience she has of the world, he'd start taking her to other places, and they'd just be two people enjoying their time together, but not! because they'd be acting under the assumption that there was nothing more than friendship between them until someone points out to Oliver that, um, technically? They're dating.
Which would cause Oliver to have a freak out and be all confused because he doesn't think of her that way (does he?) and besides, he made a choise not to put someone he cares about at risk by association. Except he's forced to think about everything and acknowledge that she's already at risk, but if he genuinely accepts her as his partner then he has to respect her choice to put herself in that position - which negates his argument for not being in a relationship. Then he'd have a moment of doubt and he'd question whether she'd even want to be in a relationship with him - she's seen his darkness, and he knows that's not something most people could deal with.
So he'd decide to up his game to test the waters, and start taking Felicity to nicer places and spending more time with her and acting like her date at work functions together - because he doesn't want to ruin what they already have if she's not interested, and he knows that she wouldn't hesitate to tell him if she had a problem with his increased attention. And eventually, she'd have her own moment of revelation about the nature of their relationship, which would send her storming into his office to confront him about it.
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timeasmymeasure
no subject
I think I'd like to see Oliver make a genuine effort to get to know Felicity beyond their existing as work colleagues and partners in crime. He likes being around her; genuinely enjoying her company and being able to relax in a way he can't around other people, because she knows who he is and he doesn't have to make excuses all the time. He would serve as an audience surrogate for the viewers to get to know Felicity better - something we all want - with the added benefit of seeing a more open and vulnerable side of Oliver.
Diggle has other relationships in his life - his nephew, Lyla, old army buddies - but Felicity doesn't have any that we're aware of, so it would be perfectly natural for Dig to be off somewhere having a personal life, leaving the other two thirds of the team alone together. And they have to eat, right? I can easily imagine Felicity saying she'd like to try such and such type of cuisine, but she's never gotten around to it, and Oliver dragging her off to try it. It would be an easy habit for them to fall into, and Oliver would keep doing it because he enjoys her company and he gets a kick out of her reactions when she tries new things.
With the understanding of how little experience she has of the world, he'd start taking her to other places, and they'd just be two people enjoying their time together, but not! because they'd be acting under the assumption that there was nothing more than friendship between them until someone points out to Oliver that, um, technically? They're dating.
Which would cause Oliver to have a freak out and be all confused because he doesn't think of her that way (does he?) and besides, he made a choise not to put someone he cares about at risk by association. Except he's forced to think about everything and acknowledge that she's already at risk, but if he genuinely accepts her as his partner then he has to respect her choice to put herself in that position - which negates his argument for not being in a relationship. Then he'd have a moment of doubt and he'd question whether she'd even want to be in a relationship with him - she's seen his darkness, and he knows that's not something most people could deal with.
So he'd decide to up his game to test the waters, and start taking Felicity to nicer places and spending more time with her and acting like her date at work functions together - because he doesn't want to ruin what they already have if she's not interested, and he knows that she wouldn't hesitate to tell him if she had a problem with his increased attention. And eventually, she'd have her own moment of revelation about the nature of their relationship, which would send her storming into his office to confront him about it.