It means that you need to have talked with Lady Akira in Witton at least once before you enter the room again to speak with her about the new events. It's just a hint that if you got all requirements for the next event steps before ever talking to her in that location, the dialog of her first encounter will trigger first, and you need to go out and back in to trigger the next dialog.
I'm happy to hear that you enjoy my game, and hope that this solves your confusion. :)