Dear Jewish Fairy Godmother:
My best friend is in her late 40’s, an English major decades ago, and
recently got a master’s/teaching certificate to teach Spanish, English
as a second language, and to work with low-level students. She has
been very involved in the immigrant community and has lived for long
periods in Spanish-speaking countries. She’s an amazing teacher, good
with troubled students, and looks good for her age. She keeps coming
in second for jobs. She’s never lacked for substitute work and every
principal at every school where she’s worked has said, I wish you
worked here. But whenever there’s a real opening she is passed over.
I think she doesn’t present or sell herself well. She just missed job
number four. Do I commiserate with her complaining or tell her what I
really think?

Dear Friend:
Most best friendships have what I call a whining clause. That allows
either party to complain about work, spouse, kids/relatives, or other
friends with impunity, with two provisos. One: what’s said in the
friendship stays in the friendship. Two: either friend has the right to
ask, not tell, the other what she perceives about a situation, though
only after the complainer has vented interminably long and has started
to repeat herself at least three times (five is better). The second is
important because people generally cannot hear or think about a
situation differently until they’re a little sick of hearing themselves say
the same things ad nauseum.

Best is not to tell her what you think but to ask questions that will
elicit the same insights and observations from her. Things like, Did you
tell them about your years in X, or your volunteer hours in y? It’s
hard. In part because you’ll have been patient for what will seem like
an eternity and you’ll just want to say, Listen up. But the more she
can own the thoughts, the more likely they are to stick. Also, once you
have integrated this technique into your communications, she’ll learn                                    and start using it on you. The good news is that it should strengthen
your friendship. So be brave and help her.