Would my intended actions with Catie fall more under Influence (using social skills and misdirection to hide true intent in the expected event that the bodyguard will be present) or Covert (assuming it's going to be a bit more sleight of hand to get a potential note exchange)?
Notes on the insides of paper cranes perhaps, always leaving one on a serving tray

maybe
Or maybe I'm over thinking it. I know I have a tendency to do that.