Dear Jewish Fairy Godmother:
I’m a middle-aged professional. My wife’s a CPA. Neither of us is a
partner yet, but we’re both trying, in our early 40’s, and second
careers. We work a lot and our two daughters, 11 and 5 are in school
or preschool while we do. We want them to have an old-fashioned
summer. The kind we had when we were kids: playing in the park,
some camp classes, but mostly free and unobstructed time, not having
to be shuttled from camp to classes, just because we’re at work all
day. We’ve interviewed three young gals from the local college, all of
whom work as nannies in the summer to earn tuition money. One
plays and teaches piano, which the older one does too. One is just
plain nice and seems ultra responsible. The third has no special skills
but the girls seem to like her a lot. How can we decide?
Epic Summer

 
Dear Summer:
On the one hand you cannot go wrong with any of the choices. On the
other, why not optimize the choice and us it as a teaching opportunity.
You can tell them you want their help in deciding, but that you’ll make
the final decision after talking to their references. That gives you the
final say and a reason to hang it on.
Have a family sit down and talk about needs, values, and priorities.
Set up a matrix of ranked items and then give everyone a sheet to fill
out. You or your wife may need to help the little one. Then compare
notes. Talk about why they liked one more or not, and what they really
want from the summer. Then check the references and talk to the gals
for a final interview, also discussing fees and flexibility of timing, which
may move you to one or the other. Whichever one you pick, keep on
good terms with the others as future baby-sitters, house-sitters, or
alternates in case number one says no.