If there was a list of things that Roy absolutely despised in this world, the first place would be being compared to Oliver. Not that he didn't love the man, also not that he wasn't aware of the fact that he had subconsciously picked up various (bad) habits and behaviors from his mentor ever since his teenage years, there were simply way too much unresolved feelings and unsaid words between the two of them. At this point the red haired archer didn't really wanna be around Oliver that much, if it wasn't for Dinah and the sake of his daughter, he'd probably have never even considered reconciliation.
However, there was still one thing that he'd tolerate, it was whenever someone said that the dynamic between you and him was the same as that of Ollie and Dinah.
Coincidentally enough, he started out as Green Arrow's sidekick, and a few years after that, you showed up as Black Canary's. You were Dinah's only protégé, and just like your teacher, you were brave, independent, good at martial art, super reliable and of course, attractive as hell.
The two of you had been crime-fighting partners ever since. If Roy was seen as a mini Oliver, then you was definitely a mini Dinah, the banters, the teasing, his shameless flirting and your no-nonsense attitude towards him, everything was basically so 'Ollie and Dinah' coded. And so of course, the archer couldn't help wanting a happy ending just like them for the pair of you as well, even if the feeling was just one sided.
"Careful!" Roy shouted as he shot an arrow towards a crook who was about to attack you from behind. "What? Not even a 'thank you'?" He said, cracking a smirk when you scowled at him, definitely with mild annoyance. He knew you could protect yourself just fine. Hell, you could probably kick all these idiots' asses without breaking a sweat, but still, the hero didn't want any of them to lay even a finger on you, and he also had to flex his talent a bit to impress you, okay? How else could he prove that he was deserving to become the Ollie to your Dinah?