Dear Jewish Fairy Godmother:

I met a woman I like at a dinner party of a mutual friend. My assets: I
am mid-fifty’s employed, a decent-looking nice guy with varied
interests. My liabilities: I am not yet divorced and I am 15 years older
than this woman, which our mutual friend says should not be a
problem. She did tell me that Sarah is recently divorced and not yet
ready for a steady. Should I just risk getting shot down and call and
ask her out. Is there a polite way to let her know I am interested
without her feeling put on the spot? I’d like her to say yes now, but I
don’t want her to be embarrassed if she wants to decline. I still want
invitations to the friend’s house to meet her again and maybe other
people. It’s been 30 years since I have dated so I am kind of rusty.

Would Be Suitor

 
Dear Suitor:

Nothing makes a person’s ego inflate more than knowing someone is
interested. That’s especially true if the would be suitor is decent-
looking, employed, and a nice person. But it’s equally true that turning
someone down face-to- face (or even by phone) can be awkward and
stressful.

 
I’d ask your mutual friend for Sarah’s email and snail mail address.
Then send a friendly invitational note that says roughly, I enjoyed
meeting you. I’d like to connect again, perhaps one on one, for any
activity you think might be interesting to do together. My range
includes going out for food and talking, a movie, going for a hike or a
concert, or taking dance lessons. Here’s my contact info. Please let me
know if any of this sounds like fun. By giving her time to think about if
and how she’d like to begin, you’ll be demonstrating your nice-guy-
ness. By including dance lessons in the range you’re demonstrating
interest in something intimate, but not in a sleazy way. A handwritten
note is more personal. But email is more modern and faster,
assuming you don’t land in her spam bin. One cautionary PS – don’t
say anything you wouldn’t want your mutual friend to read. Your note
is very likely going to be shared.