Dear Jewish Fairy Godmother:

I’ve been single ten years. I had a relationship that most people knew
about, though we mutually decided we were better as friends than
romantic partners. I also had an affair that almost no one knew about,
for complicated reasons, but my privacy was paramount among them.
It’s now over. I’ve mourned and I’m ready to look seriously for
someone new. I have a friend whom I see socially for theatre. We go
to the local indie theatre group after a good meal. She often spends
most of dinner interrogating me about my social life. I think she got wind
of my second relationship, that I had never discussed with her, though
I’m not sure how. Her questions are pointed and almost invasively
intimate. I like her other than this, but want to compromise neither
my privacy nor integrity. How shall I answer?

Gates Up

 
Dear Gates Up:

You should answer sincerely and clearly: You know, [hername], I’ve
decided that in the spirit of l’shon hara, I’m going to stop gossiping
about myself. I’ve been single long enough to realize how hard it is to
find someone I’d want to be in relationship with. I don’t want to put a
jinx on the possibilities before they have a chance to manifest. I
promise that if I get serious with anyone, I’ll be sure to tell you. I’ll
even ask if there’s a friend in the wings who might be interested in
you. But until I volunteer something on that topic, let’s talk about
other things, like work, kids, culture, and world peace.
You can expect that she’ll get a little huffy and try to test your
boundaries. But smile, deflect, and stick to your guns. If you do get
into a relationship, there’ll be plenty of time for exultation and sharing,
as much or little as you please.