Dear Jewish Fairy Godmother:

My question is pretty simple: Is it okay to try and date someone whom
you know is already in a relationship? I recently went to a Halloween
party. I know that Halloween is a time when people are not showing
their real selves, as in their I-am- an-accountant- M/F-9/5, but instead
dress up in some kind of alter ego version of who they might be in a
different or fantasy life. Many of the people at this party had elaborate
rented costumes. I went for the Middle-eastern mystery man in black
with a very elaborate facemask, the kind that left only my eyes
exposed. That allowed me to cruise a party where I knew very few
people without feeling like I had to interact in any particular way. I
saw a woman I was very attracted to, but it was clear from the
costume that she and her date were wearing that they were coupled
(think 50 shades of Halloween). But I have a very strong desire to ask
her out. What’s in or out of bounds?

Roped In

 
Dear Roped In:

Assuming you didn’t wander off the street, ask the person who invited
you to the party if s/he knows anything about the woman in question
and her relationship. Short of a ring on her finger or a definitive I’m in
a monogamous relationship and not looking to date other people, I
think you are in all’s fair in love territory. Unless you learn that an
engagement is imminent, do your best to acquire her phone number
and email. If this case I would opt for a soft approach, an email that
starts out I’m the mystery man in black from ____’s Halloween party.
It’s rare for me to approach someone who’s clearly in a relationship,
but I was very drawn to you. Would you consider having dinner with
me sometime? We can be spontaneous or plan ahead. Assume this
invitation is good for a while, though I would hope you would accept
soon.

 
Very few of us are immune to flattery. And a dinner invitation is not
officially a “date” though clearly that’s what you are implying, even
while acknowledging the relationship. Most women will at least file you
in their “options” file; some will accept your invitation, if only to
compare you to their current beau. If she says Yes, hooray. If she
doesn’t answer you will have to decide among dialing, resending the
email, or asking your mutual friend to place a delicate probe. You
could start there and ask about the history and health of the
relationship. If you do and get warned off from doing anything, you
can hide behind It’s too late. But in the meantime, date some single
people. There’s plenty to go around and those who will cheat on their
current beau are also more likely to cheat on you. Stick with folks who
have been single for a while.