Dear Prudence,
A friend of mine in my city used to ask me to cat-sit for her. The cat was very sweet and had a gravity feeder, so it initially started off as low-key check-ins every couple of days during a couple of annual trips. Over time, this evolved into checking in on the cat every day, with picture updates, during 5-6 trips per year, some of which lasted weeks. My friend also went from thanking me with a nice bottle of wine for helping out, to basically presuming I would always help her out without thanks. I was getting kind of sick of the amount of time and effort being asked of me, and was beginning to push back on cat sitting requests, when the cat died suddenly last year. My friend was devastated and took it hard, especially since she lives alone. Now she’s looking at getting another cat, and already openly discussing ways to lasso in free help from other people in watching the cat. She says she does not want to ever pay for pet sitting because she thinks it’s too pricey. I know I need to talk to her, so the question is: Do I have a chat with her BEFORE she gets the new cat, or wait until the requests start rolling in?
—Don’t Want to Resent a Cat That’s Not Here Yet