Dear Jewish Fairy Godmother:

This is a long distance Nana question. When I last visited the
grandkids (who live across the country and whom I sadly see only
once or twice a year) a few months ago, the eldest and I played chess
together for the first time. He’s smart and very used to screen games,
but relatively unfamiliar with longer, slower, hands-on strategy games.
He has access to online classes and a chess club at school. I’m not
that great, just an old fart who was taught by my father fifty years
ago. I play rarely. But I am still better than he is. We played a handful
of games together and now he wants to play with me through a phone
app. So far, so good. But his mother thanks I should let him win. I
think he should learn to get better. We’ve agreed to do what you say.

The Queen Nana

Dear Queen Nana:

I’m missing a vital piece of information which might impact my
answer: primarily, how old is this kid? If he’s five, my answer would be
different than if he’s ten. If he’s young, go easy on him now and get
tougher the more you play. You might even play while you are on the
phone or skype, so that while you’re playing you might give him tips
or say cautionary things like, Are you sure you want to do that? Or
Look around. Is anything threatening that piece?

If he’s older I would also have an explicit conversation with him about
not just letting him win. Tell him about how you learned from your dad
and how fabulous you felt the first time you beat him fair and square.
Encourage him to get a tutorial app that gives him exercises and
practice problems to solve. Chess is a marvelous brain training game.
Promise him the day he wins is not as far off as he thinks. The queen
will be dethroned.