The Honest Courtesan

I visit my regular lady about 6-8 times a year.  I recently told her that I’d be passing through her town soon, but wouldn’t be able to schedule a regular appointment.  She then said that we were going to meet for a drink or a meal.  I asked if the drink/meal would be a work occasion for her, or a purely non-work get together.  She replied, “Non work, just some nice time out of work”.  I don’t want to presume that she doesn’t expect to be compensated, but since she did not mention anything about compensation, I do not want to offend her by bluntly asking how much she would like.  What would be a good way to bring up the matter without insulting her?

I wouldn’t bring it up at all.  Most providers have a social rate, posted on their website; for example, mine is half of my regular rate.  What I would do if I were you is look up that rate on her site, put it in a greeting card telling her how much you appreciate her, and discreetly give it to her at dinner.  Even if she wasn’t expecting anything other than your treating her to a nice meal, it’s a generous gesture and she will appreciate it.  Also:  make the restaurant an especially nice one.  She’ll appreciate that too!

(Have a question of your own?  Please consult this page to see if I’ve answered it in a previous column, and if not just click here to ask me via email.)