Still Shy After All These Years

Dear Jewish Fairy Godmother:

I’m not yet divorced. But my wife relocated 2,500 miles away and we
have not been intimate for years. She has started dating where she
now lives. I’ve been shyer about getting back out there, even though I
am employed and decent looking. I’m on several local volunteer
boards where I saw a woman I’d be at least interested in. She doesn’t
wear a wedding ring. We just got assigned to a subcommittee, along
with some other folks. Should I wait to get to know her better before I
ask her out or should I take this as a sign from the universe that the
time to dial is now?

Still Shy After All These Years

Dear Still Shy:

Be forewarned that’s there no dating cliché more well-worn than “My
wife and I are separated…..” But someone whose wife is thousands of
miles away has a decent case to make.

My vote is to catch her after a meeting and say something simple, in
person rather than by phone, text or email. Be casual, as in Would you
like to go get a cup of coffee?“ which has the immediacy of surprise
and casual. Or Would you like to catch a movie sometime?“ which is
potentially more ambiguous and casual; invitational but also betrays
shyness. Or Would you like to go out to dinner sometime?“ which is
more “date-y.” I’d vote for number three and sooner, if only to get you
back in the dating game. The upside is that she is free and says yes,
you can check her out and if it doesn’t feel right, just see her in
meetings. The downside is you might get uncomfortable if she says no.
But it’s early enough that you could switch committees if things go
terribly awry. Some people, btw, don’t wear rings, so if she says
something like, Sure, but I need to alert my husband/boyfriend/partner,
you’ll learn a lot quickly. No time like now. Don’t be surprised btw, if the
other committee members notice.