From a reader:
Perhaps I am being overly scrupulous, but I have a difficult time giving gifts to my Priest, much as he deserves them. I do not want him to think that I am currying favor and want to avoid even the appearance of simony. More importantly (and I recognize that I am likely “projecting”) I do not want him to sub-consciously attempt to return the favor. I know that when people give me gifts, I tend to give them a pass on behavior and I do not want my Priest to do that, especially in the confessional.
So, is it appropriate to give him gifts, say at Easter and Christmas anonymously, or should I just suck it up and sign the thing?
I don’t think you have much to worry about on this score, but it is perfectly acceptable to give the priest a gift anonymously especially if he is your regular confessor.
At the same time, if you are inclined to be scrupulous, I would caution that in doing so against then having subtle expectations – leading to not so subtle disappointments – if he thereafter doesn’t conform or respond to something in a way you hope for.
If you are troubled by this, you might think carefully before you give him anything, anonymously or not. There are ways to show your support, perhaps around the parish, that might not involve a personal gift.