DEAR MISS MANNERS: I have three children who grew up as close friends to a neighbor of their age. She was (and is) treated as my third daughter, included in trips, etc. At the time, we were not well off financially, but she shared in what we had.
Many years have passed, and she is married with two children. She and her husband both work, but they are not as prosperous as one or two of my children. She and her family are still included in our family vacations, some of which are chosen based on the financial strain it will put on them to travel.
In the past, I have paid their hotel bill, but it led to an almost knock-down-drag-out fight with her husband, who looked on my gesture as charity.
As I explained to him, some of us are more fortunate than others in the financial area, through no fault or skill of either. What is the point of having money if I can’t spend it (in reasonable amounts) so that I can enjoy things with friends and family?
Her son is graduating high school and will be going away to college, primarily on scholarship. I want to send him more than a token cash gift. How do I do that without entering into a discussion that will cause hurt feelings? Can I gift him directly and ask him not to tell his parents? Seems rather underhanded and deceitful.
Do I have a frank discussion with the parents before sending him something? Any suggestions?
GENTLE READER: Assuring his father that it was not his fault that he is poor does not appear to have gone over well.
Putting aside the question of whether or not this should have come as a surprise, it should have been a warning. That you have money, and are willing to share it, does not exempt you from considering others’ feelings. If being the recipient of your generosity makes them uncomfortable, Miss Manners urges you to moderate your giving -- not find better ways to push your generosity on them. And do not send cash as a present to their son.