Jewish Middle Aged Dating

Ah, being a single middle-aged Jewish man and trying to understand Jewish women, now that’s a tale as old as The Torah.

So there I am, minding my own business, trying to navigate this minefield called dating. I swear, trying to understand a Jewish woman is like trying to read the Talmud without a commentary. You think you get it, but then she hits you with something and you’re back to square one, like a dreidel that never lands on the side you want.

Take my mother, for instance. She says, “Why don’t you move to New York City or Boca to meet a nice Jewish girl?” I say, “Ma, I do meet them! But then I meet them, and suddenly I’m trapped in an episode of Curb Your Enthusiasm.”

One date I went on, she spent the entire time talking about her favorite recipes. I mean, how can I compete with her grandmother’s rugelach? And when I finally brought up the courage to ask about her hobbies, she looked at me like I asked if she enjoys bobsledding. “Hobbies? Who has time for hobbies? Between work, my mother, and preparing for Shabbat, I barely have time to breathe!”

And then there’s the constant mystery of whether she’s interested in me romantically or just wants to feed me. Is she flirting when she insists I try her homemade challah, or is she just worried I’m not eating enough? I can’t tell if I’m on a date or being prepped for a second dinner. It’s like navigating a kosher buffet without knowing which dishes are for sampling and which ones are for serious eating.

Every date feels like a pop quiz where I don’t know any of the answers.

“Do you keep kosher?” she asks.

“Only when my mother visits,” I reply. Wrong answer.

“How often do you go to synagogue?” she inquires.

“Depends on if there’s a good kiddush,” I joke. Dead silence.

And don’t get me started on Passover. I mentioned once that I’ve only been to seders that end before 10pm, and the look she gave me! I’ve never felt more like a piece of leavened bread in my life. “You do know the story of Passover, right?” she asked. Of course, I do! I just also know the story of wanting to get a good night’s sleep.

In the end, I’ve learned one thing: Jewish women are a mystery wrapped in a conundrum wrapped in a brisket. And as much as I joke, I wouldn’t have it any other way. Because if there’s one thing that Jewish humor has taught me, it’s that if you can laugh at yourself, you can survive anything, including dating.

Of course most of this is my imagination because I just may have to move to Boca or Israel.