Dear Jewish Fairy Godmother:

Don’t laugh at me. I am 67 and haven’t been on a date in years. I have been
happily single for a decade, and the few relationships I have been on emerged
very naturally from friendships and then ebbed back into same, after a lovely and
satisfying interlude. But now I said yes to an actual coffee date. It’s not just “out
of practice,” because I don’t think I ever was in practice. What does one talk
about? What should one not talk about? Are there unspoken rules of etiquette
that other people know but I somehow missed? Should I “just be myself” or is it
more important to create a good impression and let all my flaws come out later,
more naturally? Other than saying “No thanks, I changed my mind.” Do you have
any good advice?

New Again

 
Dear New Again:

This may sound silly or too simple, but here goes. Don’t think of this
as a date. Yes you want to get to know the other person, and the
other person wants to know you. You’re both in the “business” of
buying and selling. So that’s four personalities/observers sitting at the
table, all of them busy taking notes and listening for red flags like, All
my exes sponged off me. Or I don’t understand how anyone would be
married to someone who______.

 
It’s fine to display preferences and personality. Try to keep your
stories short and both informative and interesting. Don’t hog the
airtime and genuinely listen to what you are being told. See where
your interests converge or diverge. Don;t worry about remembering all
the names and dates but listen for big arcs of story, like cities lived in,
professions, marriages, home ownership, and children. You can always
go back and ask for details if you get to date number two. Most
importantly, believe what you are told. If a date expresses a history of
infidelity or bankruptcy, take note. Ditto for good works or personality
traits you seek.

 
Allocate two hours for this exercise, but ask a friend to call or text you
about an hour in, with an ostensible emergency. Then if you need to
flee, you can have an excuse. But use this only if it’s really really bad.
You’ll know if you want to get together again.