Dear Jewish Fairy Godmother:

I just got asked to join a “meet up” group for single adults over 60.
One of my friends, actually an ex, is hoping to have new alternatives
for dinner and movie excursions etc. The idea is to post “I want to do
X, Y or X at a certain day/time. Does anyone else want to come?” I
very much prefer one-on-one to group activities and also value my
time and whom I spend it with. I mostly want to have friends but
would consider dating if there’s a click. Ironically the same person
caught both our eyes. What’s the etiquette here?

Single and Only Sort-of Looking

Dear Single/Looking:

As tempting (and childish) as it is to “call dibs” on the prospective
datee, that’s not how adults, especially those who’ve been around the
block for decades, conduct themselves. Agree upfront that you will be
honest with one another, and that you’ll stay friends regardless of the
outcome.

 
Like Solomon and the two mothers who covet the same baby, you’re
each going to have plead your case, not in so many words but by
being a charming date.. If the friendship is worth its salt it won’t
matter if the object of your affections chooses either or neither. Flip a
coin to see who invites her to dinner first. Be very clear on this quasi-
date that while you’re looking for friends, you definitely would like to
know this person better because if you “met the right person…..” Be
clear about your relationship history and see if that level and topic of
disclosure is reciprocated. It is critical that you speak only well of your
friend to the date. Don’t be sly or coy. End by offering your contact
info and say (assuming it’s true) that you’d like to connect again for
fun and food. Then the other friend does the same, leaving it up to the
date to decide which, if either of you, gets the next chance to connect.