Dear Jewish Fairy Godmother:

I’m a year out of a nasty divorce and ready to date. By finally I mean
post divorce trauma and also my first date ever. My ex and I were
high school sweethearts who were married for thirty years. I have
never had to ask out a stranger and I am really unsure what to do. I
like to go walk on the beach and in the woods, and it seems to me that
a perfect first date would be to do that, and then go grab some food.
It would give me and the date a chance to do a lot of talking, but not
in the intense way of speed dating. My friends have people they’re
ready to fix me up with. Do you have any tips for how to look like a
great catch, assuming I want to get caught?

New At This

 
Dear New At This:

When you make plans, be considerate of your date’s preference. Ask
about locale, distance that would be comfortable, time of day, weather
contingencies, and all the things that can make an outing into nature
more fun than disaster. Equip your car with a set of walking poles and
offer your date one. Put a couple pairs of warm dry socks and some
dry footwear in too, as well as a thermos or two of coffee/tea and
treats for before/after. Bring along some trail mix or energy bars, and
water bottles. Try to look like a considerate host rather than a
paranoid Boy Scout.

 
The hard part of first dates is learning a lot about a person without
sounding like The Grand Inquisitor. Ask leading questions about what
your date likes to do for fun, about food, music, movie, and book
preferences, and work life. Avoid asking about or complaining about
exes, physical ailments, financial crises, or other subjects that will
make either of you seem like a whiney deadbeat loser. Listen carefully
but without jumping to conclusions. Try for a mix of companionable
humor, intelligent conversation, and just enough cool mystery that
your date will want to see more of you. Then hope it’s mutual.