Thank you for weighing in everyone (and nice to see you Wwanderer!). Human relationships are always complex—there's almost no one in the world whose company doesn't offer me happiness in some ways, and also no relationship is perfect. If the lady in question point-blank
hated the gentleman in question, it wouldn't be much of a question at all.
The perfect courtesan is supposed to be able to intelligently and diplomatically converse on a wide array of topics (on how many websites have we seen this phrase?). The advice/experience I was looking for was more along the lines of—is it worth it to engage with someone at all when you find yourself in the position of my friend? Is it reasonable to ask that certain topics not be mentioned? How does one balance being a paid companion and a real person with opinions, and what are you actually being paid for (your true self/mind/personality, or who someone wants to believe you are, particularly when this is antithetical to your own values)?
Anyway, my questions have been more than answered and I appreciate everyone's advice. I'll spend the rest of the day mourning the loss of WTF's admiration, if I ever had it in the first place.