Out of Shape

Dear Jewish Fairy Godmother:

I’m 62 and I need dating advice. I have been single for almost ten
years, not for lack of trying. I just don’t seem to meet anyone who
interests me and I think is attractive who feels the same about me. I
just met a potentially lovely person through new mutual friends. They
moved here and had a big housewarming party; many of their friends
from two hours away attended. One was Sarah, whom the wife of the
couple had confided previously, was single and looking. We had a very
brief conversation (tea not coffee) but she didn’t give me any negative
signals. I am going to her hometown for a birthday party very soon.
Should I: Call the mutual friends and see if she said anything about
meeting me? Ask them for her phone number? Look up her number
online? Find her email from the invitation list? Call or write? Ask her
for a date? For tea? And what tone should I take?

Out of Shape

Dear Out of Shape:

You sound more like a nervous teenager than a senior citizen. But I
agree, dating doesn’t get any easier with time. I would vote against
putting the mutual friends in the middle. It sets up a bad dynamic
early in the potential; relationship. If you do end up going out, they
will find out soon enough. If you ask her out and she accepts, you can
happily tell them after the fact.

I vote for a simple email. Hopefully you can find hers without having to
ask. Try to write the way you’d talk, simply and accessibly: [Name] –
Nice to have met you. It would be great to continue our conversation
(or start a new one). Coincidentally, I&'m coming to [town] this
weekend for a friend&'s birthday party, and then visiting other friends.
Let me know if you&'d be up for a teahouse connect, and when would
work for you. I&'d enjoy it – hope you would too. You can find me on
email or phone #. Give her a few days to respond. If you don’t hear
back, do nothing else. The next time you see the mutual friends, tell
them casually that you tried to connect. If there’s a message back you
need to hear, they’ll tell you.