Life & Culture

My first date rules as a Jewish matchmaker

For a start, I've learned moving too slowly can kill any connection


Man and woman, sitting outdoors in cafe together.

Of late I have had a string of fine first dates with some nice guys who have respected my 90-minute first-date rule.

Some led to second dates that were also, just fine. However, I’m looking for more than “fine” when I am thinking about the prospect of a relationship. I’m a sparky person, a hopeless romantic and fine will never be enough for me. And nor should it be for you.

We shouldn’t just settle for things in life, and especially not in our dating lives.

My series of fine first dates was followed by a rare gem of a first date. It was up there with one of the best first dates I’ve ever had.

And that’s a bold statement for anyone to make, let alone a matchmaker who’s already been on more than 30 first dates this year.

Let’s call this man Gary. I had an inkling he was going to be a decent date because Gary’s pre-date chat had been light, fun and, most important, consistent.

That said, anyone can perform well behind a keyboard, right?

But lo and behold, Gary delivered on the date. He was funny (which is a top-tier pull for me), charismatic (in other words, can talk the talk) and had gentle-mensch (a gentlemen and mensch) qualities.

I broke my 90-minute first-date rule and gave Gary circa six hours of my time, something I have only done on a few occasions in my dating career thus far.

Now, Gary was confident on our date that we would be going on a second. In my head, I was thinking, yep, we probably will but I didn’t give too much away because let’s remember, I don’t actually know this guy.

While we have to be vulnerable when we’re dating we should also always proceed with caution. Is he going to put his money where his mouth is and lock in this second date?

I left the date intrigued and excited by Gary, but here’s the thing: his post-date communication wasn’t so exciting. We kind of arranged a second date but it felt non-committal and it never happened.

Gary is what I like to call inconclusive. Not ballsy enough to call it quits or to get us to a second date.

He didn’t ghost (Mazel tov, Gary) but we’re not into guys who promise the world and deliver nothing.

He could have been one of those guys that gives every girl they date a great first date, but they actually fancy only themselves and aren’t interested in, well, anyone. But something tells me Gary wasn’t that.

Moving too slowly can kill any connection you have with someone. A part of me would have preferred he had gone Casper on me because I am just as baffled as you are.

Sometimes you meet someone and it begins and ends with a great first date.

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