There are a few things you can count on in life: death, taxes, and a Jewish person turning any conversation into a connection within three minutes. It always starts innocently enough. You meet someone new at a soccer game, a school event, a bar mitzvah out of town, where you only know the host, and within seconds, it begins.

“Where are you from?”
“Chicago”
“Wait. What part?”
“North Shore.”
“Stop. Do you know the Goldsteins?”

And just like that, we are off.

There is a running joke among my friends that while the world operates on six degrees of Kevin Bacon, Jewish life runs on two, maybe three of Ali Cantor. I wish I could say that’s an exaggeration, but honestly, it’s not far off. Somehow, somehow, I’m always one or two connections away from whoever comes up in conversation. And if it’s not me, it’s my cousin, my daughter, or someone from camp or college.

Jewish Geography may not be an official Olympic sport, but it absolutely should be, and for once,  I would have a real shot at earning a medal. Back in law school, my friend Russell used to test me; he would randomly throw out a name from my social media and challenge me to come up with five fun facts about them. Five facts meant I actually knew the person. Twenty-five years later, he doesn’t even bother asking. He already knows I’ll win.

Jewish Geography is a skill set, honestly, with speed, precision, and a deep bench of connections. There is no warm-up, no small talk. We skip straight to “Wait, how do you know them?” like it’s a professional obligation.

Social media has only taken the game to another level. Even when I don’t really know someone, I somehow know them, through tagged photos, mutual friends, or that one person who mysteriously appears in everyone’s pictures. The web just keeps growing, making the game faster, sharper, and nearly impossible to lose. Of course, a great memory gives you a leg up in the game.  

Here’s the thing: it almost always works.

Somehow, you do know the Goldsteins. Or your cousin dated their neighbor. Or your daughter goes to camp with their niece. The degrees of separation collapse at an alarming rate, and suddenly, you are not strangers anymore, you are practically mishpacha.

I’ve watched this happen everywhere, at theater rehearsals, at cheer competitions, in line at coffee shops, but especially on vacation. Honestly, especially on vacation. Anywhere in the U.S., even across the world, at any time.

You could be standing in the middle of a resort over winter break, fully convinced you’ve escaped your everyday bubble, when suddenly you hear “Ali?” Maybe this only happens to me, but I’m pretty sure it doesn’t. There is always someone who knows someone who knows you. It is instant, it’s inevitable, and it’s actually kind of amazing.

Take it from me, Aruba at Christmas time isn’t just a getaway; it’s basically a pop-up community.

And the funny thing is, it doesn’t stop at the conversation. Some of those quick connections have turned into real friendships. We visit each other when we are in different cities, show up for their kids’ mitzvahs and weddings, and stay in touch long after the vacation ends. My Aruba friends? They are the real deal.

There is something both hilarious and comforting about it. Jewish Geography is less about showing off who you know and more about finding your people, fast. It is like we are all walking around with invisible threads, just waiting for someone to connect them. And once they do, everything shifts. The conversation relaxes, the distance disappears. You are no longer making polite small talk. You are swapping stories, comparing notes, filling in the gaps, and adding friends on Insta.

And while it can feel a little intense, maybe even mildly invasive if you’re not in the mood, it is also kind of beautiful. 

In a world that often feels huge and disconnected, something grounding happens when we realize how small and intertwined our community really is.

Especially now, with everything going on, there’s comfort in that closeness—a reminder to hold onto each other a little tighter.

Because at its core, Jewish Geography isn’t just a game. It’s a quiet way of saying: you’re not alone here—a way of turning strangers into something closer, something familiar.

It’s not about the Goldsteins. It never was. It’s about belonging.