Whenever you want to start the date night with Roy, I'm game. I'm really open with what to do with it. Roy doesnt really have a secret identity as Arsenal. If Cat were to google him, though, she wouldnt see anything about him being Speedy or a Teen Titan when he was younger. She'd see that he was Ollie Queen's ward, had some time in a rehab facility after Ollie booted him for being on drugs, and afterward kind of dissapeared, and his official status was "Agent for the Central Intelligence Bureau". Cat strikes me as the kind who would want to know who she was going out with.
From there I'm thinking all kinds of fun stuff can happen on the date. Random super villain, random drug bust, random one night stand.... fun! Any ideas?
And, at some point, Dick and Roy need to run into each other. ;)