Substack is not a dating site

But it could be

I spent most of my 30s on dating sites — not because I couldn’t date IRL — but because I preferred it.

Online dating let me get to know someone without all the surface-level distractions. Such as what they wore, how they looked, or worse… how they smelled. (Let’s be real.)

It gave me a direct line into their brain. It let me figure out if what was in mine would vibe with theirs.

Some of the best people I’ve met came from an online dating site.
People I never would have crossed paths with in real life.
We connected over things that went deeper than looks — politics, weird hobbies, obscure obsessions like dive museums (yes, that’s a thing).

Could I have met them offline? Maybe. But how much time would that have taken?

Most of those connections never turned romantic. But they still left a mark. Some of them are still in my life today.

OkCupid was my favorite

Back then, OKCupid was the place to be. I’m not talking about today’s OKCupid — I mean the original, pre-acquisition OKC (2010) until it finally died around 2018.

Before Match.com bought it and turned it into a waste of time.

Unlike Tinder, which banked on immediate attraction, OKCupid had… questions.

Lots of them.

It was kind of like eHarmony but without the matchmaking nanny hovering over your results. You got a match percentage based on your answers, but it was up to you whether 89% was good or if 31% chaos energy was more your thing.

For me, the sweet spot was around 80%. Enough in common to connect, with just enough difference to keep it interesting.

Some questions I remember:

• political beliefs

• sexual preferences

• lifestyle stuff

• relationship goals

If you’re interested in seeing specific questions, here’s a list of some of the questions (thanks to a wonderful netizen who posted it to Reddit years ago).

Some people said the questions were invasive. I thought they were gold.

At one point, I tried to answer every single one. I think I got through several hundred. Then the acquisition hit, and the questions got weirdly biased and off-topic. So I stopped. But I still answered a lot.

Here’s what made it work for me:
It connected people based on ideas. Not just looks.

If that’s what you were looking for, it was magical.

Now, here’s the weird part

Substack is giving me the same feeling.

It’s not a dating site.
But it could be.

Substack Notes, in particular, are low-key recreating that original OKCupid energy.

They connect people based on content. Not photos. Not filters. Not flashy bios.

From what I’ve seen in just a week of using it, Substack Notes shows you things written by people who care about the same stuff you care about. Even if you don’t follow them yet.

What kind of stuff? Not just political leanings or lifestyle takes.
Deeper stuff.

The kind of stuff you write when you’re being honest. When you’re not trying to brand yourself, you’re just trying to understand the world out loud.

That’s the kind of content that draws people in.

People like you.

Why it feels like dating

When I say “Substack feels like a dating site,” this is what I mean:

• It’s a feed of short-form content, just like OKCupid profiles.

• You engage by clicking on something that grabs your attention.

• The more you engage, the more you train the algorithm to show you your people.

• You get to follow, comment, and restack. It’s low-pressure. Like messaging a maybe-crush.

• If you like someone’s vibe? You follow them. Maybe even DM them. That’s how friendships start.

It’s kind of wild.

On OKCupid, your content was a bunch of profile Q&As.
On Substack, your content is your writing. But it’s still doing the same thing.

It’s showing the world how your brain works.

And when someone else’s brain feels like a mirror — or a perfect contrast — the connection happens.

---

What about blogrolls?

You could argue that this isn’t anything new.
Blogrolls did this in the early 2000s.

A blogroll was basically a curated list of “blogs I think you’d like.”
Comments connected creators.

But blogrolls were static.
Notes are alive.

Blogrolls were curated manually. Notes are algorithmically surfacing content based on signals.

Blogrolls were polite. Notes have flirt energy.

And now? A simple restack can expose your work to 10,000 new readers. Or your next collaborator. Or your next best friend.

Here’s what I realized

Platforms that surface ideas instead of images build different kinds of relationships.

That’s what Substack is doing — on purpose or not.

People show up raw here. Unfiltered. Messy. Curious.

And that means the people who resonate with your words?
They might be your people.

Not your “content niche.”
Not your “target audience.”
Your people.

So no — Substack isn’t a dating site.
But if you’re open? It could connect you to the kind of people you actually want in your life.

And honestly? That might be even better than a date.

---

We don’t need more platforms to scroll.
We need more places to connect.

Substack Notes might just be the unexpected matchmaker you didn’t know you were looking for.

Hit follow. Send a note. Restack something.
You never know who you’ll meet.