Dear Jewish Fairy Godmother:

What’s the protocol when both you and a friend want to date the same
person? About a year ago I was told that a certain widow was
potentially ready for a relationship. I was a little cautious because she
has two pre-teen sons, one of whom was described as “a handful.” But
I made a point of attending adult ed classes she was in and
schmoozing her at onegs, generally seeing if there was any kind of
interest or if I was attracted enough to be willing to overcome a
potentially deal-killing pair of liabilities. Just as I was deciding to ask
her out, one of my closest friends said he was interested in her. He
said he’d been invited to a circle of giving at her house, and had been
impressed with various things about her. I mumbled something like,
Yeah I’ve been thinking the same, and we both glided away from the
topic. So now I’m not sure what to do. In reality they’re probably a
better fit, and he’s raised boys where I have not. But I’d like a chance
to find it if there’s any there there, plus she’s minus twenty pounds
lighter and more attractive.

Preempted?

 
Dear Preempted:

You’re not off the board, but I think your friend has the right to ask
her out before you do, simply by virtue of having spoken about her
aloud first. You do owe your friend an honest conversation. You can
say you’d been thinking about dating her also, but had wanted to give
her time to be ready to date. As in any negotiation, there’s no point
airing your concerns about her children, just in case your friend might
quote you (accurately or not) on their date.

 
After your convo, you should each call to ask her out, perhaps for
successive weekends. You can try to impress her with tickets for an
event, but I’ve generally favored the leisurely drinks and dinner with
sharing life stories as a great way to assess a potential relationship.
While you’re listening to her, keep a careful ear open to how she talks
about her kids. After you and our friend have each had a date with her,
go out for coffee and agree who’s more likely to give her a fair
shot at a real relationship. It sounds like she has enough on her hands
without being a trophy in some who can bed her first battle between
buddies, and is probably more worthy of someone who can see past
the superficials.