Oliver wished he had been imaging the kid following him around Star City. Felicity had mentioned it off-handedly (but really handedly) but he figured it would go away. This city was dangerous and he was the one running towards it, not from it. He figured you would understand that soon enough.
Unfortunately for Oliver, you didn’t. Instead you got bolder, sticking around after the problem was taken care of to call after him. He never stayed back though. Eventually, you got downright shameless (in his opinion) and turned up at the club, asking where the Green Arrow was.
That was why he sat here on this rooftop, listening to your proposal to make you his sidekick. His new speedy. He would laugh if he wasn’t concerned about how far you would take this. He didn’t need you to be involved in this, not with what happened to Roy and Thea and not without knowing anything about you. “This is my crusade. I’m not putting a kid in the middle of that” His voice was firm and gravelly as he walked away, preparing his arrow.