Dear Jewish Fairy Godmother:
I have a sister who is five years my junior. We were never very close
for reasons too numerous to explain. I married early (at 20); she
traveled extensively over the years. We are now closer than we’ve
ever been, at 66 and 61. I have been married living the good life for
many years. She is a clinical psychologist and I am sure that her
income is not nearly as high as mine. I would like to help her when
and if she need financial assistance. She has never asked me for help.
On a recent visit to my home, we walked and talked and had a good
visit. At breakfast I asked her about her yearly salary. She said it was
none of my business. I have never before asked anyone what their
salary is. I asked so I would be able to give her money from time to
time if I felt it was needed. She was upset. At that point I told her that
we could never be close. Was I wrong?
Big Sister

 
Dear Big Sister:
Your motivation wasn’t wrong but your execution seems to have been.
If you’ve never asked anyone else this question, there’s a reason. It’s
intrusive, sometimes more so among people who are close than
relatively new acquaintances or professional colleagues. It’d been
better to have asked in general, Do you ever feel tight for money?
Would you be able to accept money from me in those times? Or better
yet, to gift her without making it feel like charity in a way that might
make her feel shamed.
Best would be to treat her to things where you’d enjoy her company,
without making a big deal about it, or in a way she’d feel you were
lording your status over her. Invite her to join you at everything from
dinner and a concert to a vacation. Tell her that you enjoy her
company but don’t want to impose the costs on her. Say that if she
can make the time, you’d like to make up for the years you were not
as close. She may see through you. But time is getting shorter. Make
up and enjoy her while you’re both well enough to be together.