Single and Looking

Dear Jewish Fairy Godmother:

I have a big crush on the boss’s assistant and I’d like to ask her out.
Should I check in with the boss first — not that she’s his “property”
but just to make sure it wouldn’t be weird?
Single and Looking

Dear Single/Looking:
Crushes are almost always dangerous, at work or not. The big zap
usually has a big come down. But they’re also hard to shake without
another object of affection on the horizon. I am going to give you a
30,000-foot view first and then narrow into your circumstances. Some
of what I’m gonna say is true for everyone, no matter they work, from
a big-box warehouse store to a brokerage. Other parts will be specific
to your immediate circumstances, but only you’ll know what those are.
Think about what you do when you use a crate to train a puppy: you
make sure the dog won’t poop where it sleeps. Sure it’s hard to meet
people when you work full time; but it’s also silly to potentially
endanger your job by dating someone who may have the ear of the
person who controls your paycheck.


Check the company personnel
policies. See if there are specific policies that set guidelines on inter-
office dating, for example, not among people who supervise one
another. Then ask the Human Resources director if there are other
policies. A lot, btw, depends on whether your office is 200 people or
five. Either way the woman will have a network of gal pals with whom
she’ll share much of what you tell her (in early dating stories) and
perhaps even intimate details (if this progresses). Do you really lust
for zero privacy?

My vote, go out for coffee or something casual after work (Hey do you
want to grab a bite or a brew?), a casual could-be- friendship-and-
nothing-more, somewhere between collegial and a date. If, after not
during your hour/two together, you are genuinely interested, ask her
what she thinks about office romances. If she’s not completely
opposed to them (read that, if she likes you) go out for coffee again.
Agree on rules, saying it will protect you both. You have to assume it
will end badly, not because I am sure from here, but look at the odds
of romance and even marriage.


Also, be careful what you say in
emails. That’s not to say things cannot be misquoted/misattributed.
Remember she’s closer to the boss than you are, so handle that
communication carefully. You can say something casual to the boss, I
really like Sally; we’re going to start dating. Wish me luck. But mostly
it’ll make him watch you and her more carefully. My gut tells me                                  you’re walking too close to a land mine; isn’t there someone in the
mailroom you like? Sign me Cautious Cynic, or Seen This Show and It
Usually Ends Badly. Write me in six months if you’re dating and I’ll eat
this advice.