Tales of Jewish Dating, Part II: Vital Lessons Learned

In my last post, I told many stories about the less-than-perfect experience I had with shadchanim and Jewish dating. I’d like to speak about some things I learned from these experiences.

Not All Shadchanim are Created Equal

First, not all shadchanim are made equal. Some really take the time to get to know you. It doesn’t feel like a matchmaking factory, where they’re sending you out constantly, hoping if you go out enough times you’ll hit pay dirt. They actually want to connect people for whom they perceive a logical connection. And their heart is in the right place. Your long-term tranquility and happiness is the center of their concern.

Others… not so much. It’s a numbers game. They toss people out, knowing full well that if you shoot enough times at the target, you’re bound to graze the bullseye a few times. The elephant in the room is that this type of dating is horrendous, with potentially disastrous long-term results. Dating can get very expensive, and it’s really difficult emotionally. Jewish dating in my crazy city is not fun. It’s often a highly pragmatic marriage interrogation. If it works out, great. If not, you have nothing to show for it. Just lost time and money. No new friend or connection. No amazing experience. Just another failed attempt to find “the one”.

And what happens when it does work? What happens when you toss people together enough times and at some point they do get married? Are you creating healthy, long-lasting relationships based on trust, shared values, and quality communication? Or are you just tossing people in the same room and letting the chips fall where they may? And then abandoning these young, ill-fated couples to figure it all out on their own?

I’m sure there are shadchanim out there who are skilled and thorough. And I’m sure there are those who just have a knack for what they do. The others should stop. They’re doing more harm than good, all positive intentions aside.

Interpretation

Another lesson I gained is about terminology. There are phrases I would use to describe myself that I would never use again in front of a shadchan. I consider myself to be extremely open-minded, especially relative to a lot of folk in my immediate vicinity. However, I quickly learned that whereas I mean that I am open to all sorts of different thoughts and ideas, and I’m willing to try many things in life even way outside my comfort zone, the term seem to get misconstrued by shadchanim as “has no standards”.

So, if you want a shadchan who goes through a list of those who as of yet no one wants to date, by all means tell them you’re open-minded. Please be aware: The damage to your self-esteem upon seeing the type of people you get set up with could crush your soul.

If you want a shadchan who goes through a list of those who as of yet no one wants to date, by all means tell them you're open-minded. Share on X

Jewish Dating, a Bit Too Serious

A final lesson I culled from the Jewish dating process is it saps your will. It could certainly be expensive. It is most definitely time consuming. But more than any of that, the emotional drain is severe. Keep in mind, this is a very serious form of dating. You’ve got two people interacting, both who wanted to be married yesterday. Hell, they want to have three kids by now! There’s no time for letting go and just enjoying the moment.

In fact, the best date I ever went on was, by Jewish dating standards, an absolute failure. We learned very quickly that we had certain values and lifestyle choices that didn’t mesh correctly. Marriage was out of the question, therefore so was continuing to date. However, we were already there and enjoying each other’s company.

I recall very little about this young lady. I don’t even remember her name or what she looks like. But I will never forget the hour and a half we sat just chitchatting on a bench in Jerusalem, eating sunflower seeds and spitting shells all over the place (Israel’s simultaneously most revolting and most amazing custom). The conversation was fantastic. All pressure was 100% gone. And we sat there with the ability to enjoy ourselves, without a care in the world.

It’s actually funny. When going on a date in any capacity, the advice everyone always gives you is to be yourself. And yet with this style of dating, it’s so rigid and uncomfortable that being yourself ceases to be a viable option.

What’s next?

And when all the smoke clears, the date usually ends one of two ways: You either continue on the marriage trajectory, zooming your way to a new apartment filled with wall-to-wall children. Or you have nothing. Nothing at all. No friendship has been created, nor do you have a long-term, meaningful connection. No adventurous story has been added to your life. You just move on to the next uncomfortable moment, hoping that this one will be different. And you try to forget this lousy moment, and the time from your life you will never be able to get back.

Again, I’m sure there are those who try and set people up with the finest of intentions, and who are thoughtful and caring about really trying to put two people in the same room who actually should be. And thus quality dates and marriages might result.

That was not my experience.

Nope. I met my wife on a bus. And sure, it didn’t work out in the end. But we hacked 13 years together. Seems better than most this day and age.

And I’d still take a bus over a shadchan any day of the week.

In my next post I’ll talk about some more important lessons I culled from these last insane 20 years.

Anything you learned from your experiences?