Arrow 5x05 using that time to have Diggle bond with Rene is a good moment, and it's also totally in character for Oliver to feel like that is something Diggle is more capable of and to hand it off in that way. BUT. It would also have been a good chance to have Oliver-- the resident expert in being tortured-- get closer with Rene.
Or you could strike a balance. Have Diggle do most of the conversation with Rene. Then later have Oliver just drop to Rene the fact that he's been tortured multiple times, in that way that he has of just throwing out one stray bit of information about his past without context as if its a casual thing (i.e. "I've been an assassin" or "a week in cage will change your perspective on a lot of things. trust me.") but that is almost certainly both calculated and something he had to kind of work himself up toward because talking about what he's been through is so hard.
So later on in the episode Rene makes some further attempt to apologize to Oliver for outing him to Church, and Oliver says something about knowing what it's like, and definitely leaves Rene with that impression that he has been tortured more than once, and then he walks away. And it's calculated to show Rene that he's not mad at him, but also to end the conversation and to disrupt Rene's perception of "Pretty boy, rich kid Oliver".
Felicity Smoak Is One Brave Precious Badass Cupcake! #32
As we all know Felicity is a precious badass cupcake! I figure it can’t hurt to look at the many acts of bravery she has performed because let’s face it - our girl rocks!
Arrow 5x05 - So many feels for Felicity in this episode she clearly still loves Oliver, I think it hurt to hear Oliver encourage her to move on...the pain was never far from her face in 5a and these gifs show it so well!
Arrow 5x06 - The physical distance between Felicity and the man she loves when she needed him most, I know it was self-imposed but it still hurts
Arrow 5x08 - Not going to lie, did not love this episode but even the alternate reality Felicity was amazing
Arrow 5x09 - While awkward, Felicity held her own with Oliver’s date, poor woman never really stood a chance
Arrow 5x09 - Felicity’s sass was on clear display between the line below and asking why don’t guys listen?
Knowing what we know now, after 5x20, this scene in 5x05 gains much more depth. We learned that over the summer, Oliver and Felicity hooked up (made love) and then hit “pause” on the talk they desperately needed.
After licking his wounds, Oliver held onto hope that he and Felicity would work things out, eventually. She was open to talking it out when she was ready, and Oliver was going to wait for her. He’s a patient man, and Felicity is the love of his life, so he’d give her the space and time she needed.
When Christopher Chance called Oliver out on preferring the hood over “Oliver Queen,” he said:
“That’s not the reason.”
It’s because he’s waiting for Felicity. Because she’s the only woman in his life, the only woman he’s interested in romantically. Because she’s the love of his life and worth waiting for. The woman he made love to not long ago, allowing him to express the love that’s bursting out of his pores, a woman who basically promised to talk it out with him, at some point in the future. All those thoughts are running through his head as he negates Chance’s statement. And as Chance starts to say he’s the last person to give dating advice, Oliver has already started tuning him out, because Chance is well meaning, but wrong.
And then, Chance drops the bomb.
“Felicity moved on.”
Still thinking, pondering, hoping...
Wait for it...
That’s the moment his heart drops, his lungs seize, his gut churns. Wait, what?
It takes all of his will to keep a neutral expression, but on the inside, his chest is caving in. His hope for reconciliation is hanging by a thread. He’s shocked, and hurt, that Felicity didn’t tell him. He thought they were on the same page. And the only word that rings in his mind is, “Why?”
Felicity responds with an attempt at humor, but Oliver gives her his version of the head tilt. Then, (GROWTH!) he talks about his feelings.
Ugh. He swallows back his pain as his heartbreak knocks him back.
Felicity tries to explain, that every time she was going to tell him, she chickened out. Oliver clings to that thread of hope in his heart, and looks for any sign that his hope is justified.
She shuts it down, a little too quickly. Doth the lady protest too much?
The thread pulls taut. His heart clenches at her answer, so he breathes against the pain.
It hasn’t snapped yet. He’s hanging on by his fingernails. A question is burning in his throat, a question he’s afraid to ask, because he’s afraid of the answer. But he has to know, so he takes a deep breath and braces himself.
That tight feeling in his chest loosens as hope is...not quite restored, but not lost, either. Oliver’s a stubborn man, his best and worst quality, and he’ll cling to that little bit of hope for all he’s worth.
That little bit of hope was enough to sustain him in the ensuing months, tucked in a corner of his mind, steady enough to keep his head on (mostly) straight.
Stuff happened. Crazy stuff. Let’s just leave it at that.
Then, 5x20, present day, they finally, finally, have that talk they so needed. The air is cleared. Deep secrets are unearthed. Compassion and understanding heal the cracks in their relationship.
And then...
She opens a door that once was closed, and the hope that he clung to deepens and grows. His patience has been rewarded, and he’s overcome with emotion. There is now a clear path to reconciliation, a path that includes forgiving himself, loving himself, and finally becoming whole. The love of his life will be waiting for him at the end of this path, ready to join him on the next one.