Dear Jewish Fairy Godmother:

I’m 55 and I’ve been single for six years. During that time I had one
extended “friends with benefits” scenario that ended when it got too
emotionally messy. We are finally back to friends again. Then two
crushes with highly inappropriate people that backfired and cost me
some emotional health. And one affair with a married guy who claimed
his wife knew that blew up very badly. I’m a year out of the last
scenario and have spent a lot of time working on my emotional issues
and history of bad choices. In fact, my life seems so harmonious and
calm without all the drama of relationships that I have become a little
scared of dating. A friend wants to fix me up with someone she thinks
I’ll click wit, though another fiend knows the guy in question and sees
nothing in common. Do I risk turning my peaceful life upside down
again, or just slide into old age on my own?


Dear Single:

Life expectancy suggests you have several decades in front of you.
That’s a long time to be alone if you are in fact the kind of person who
likes to be coupled. Your history suggests you do, though the
demographic tends in America are for increasing numbers of single
households. Many people who have been married for their whole life
find a new freedom in being single. They blossom into a new life after
a late life divorce or widow/widowerhood.

My vote: make the call. You’re unlikely to spend the rest of your life as
a hermit, and even if the connection doesn’t turn into something
romantic, no one can have too many friends for movies, dinner,
concerts, etc. And the truth about dating, as a wise person once said,
is that it’s a numbers game. The more people you meet and greet, the
more chances you have to find someone special. In addition, every
one of those people has friends who are also single. So if you conduct
yourself honorably, they may get points from the other people in their
lives if you get passed on to someone else in their social circle. There’s
a world of singles who don’t want to be. While your ambivalence is
understandable, it’s also ready to be tested by scenarios that are more
viable. You say you’ve worked through your issues. Prove it to yourself
by dating other eligible singles and change your patterns.