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!
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