Hello stranger! The 30-day trial.

In May, I decided to dip a toe into the online dating world.
After what felt like hundreds of swipes, here’s the scoreboard:

36 likes.
7 messenger conversations.
2 text message exchanges.
2 dates planned.
1 actual date.

Not exactly a rom-com highlight reel.

A friend of mine, Kathy, once wrote in a blog post:
“Sometime between my life before marriage and my life after marriage, dating changed. Or men changed. Or maybe I changed. The playfulness of dating has been replaced by nice-to-meet-you goodbye.”

That line stuck with me. It felt true back when she wrote it and maybe even more true now. My time on the apps was brief, mostly because I still believe in face-to-face energy. I struggle with the idea that chemistry can be measured through curated photos and carefully worded bios. Profiles don’t make me feel anything. People do.

Online dating is a tool — nothing more. It can open a door, but it can’t replace the moment you sit across from someone and realize whether something real is there or not.

So how did the one real date go?
Simple. We met for dinner, talked easily, then wandered for shaved ice afterward. There was laughter, kindness, and that quiet understanding that sometimes two good people just don’t spark. No awkward promises, no forced “let’s do this again.” Just a genuine goodbye. And honestly, that felt respectful. I met someone kind, learned a little about her world, and that wouldn’t have happened if I hadn’t tried.

But the more entertaining story is the date that never happened.

I’ve heard plenty of women say “men are jerks,” and just as many men say “women are crazy.” Maybe neither side is right. Maybe both are. Maybe it’s just humans being humans, colliding awkwardly in the wild west of dating apps.

This almost-date started with the usual rapid-fire questions, a few photos, some playful banter — the normal early dance. The night before we were supposed to meet, she texted that she was feeling anxious, then quickly reassured me she had it under control. Fair enough. First dates are weird for everyone.

Then came the morning message: she couldn’t make it because she had a knot in her hair.
A knot.

I teased lightly, curious more than anything, and joked that I had to see this legendary knot. Moments later, I’m staring at a photo of the back of someone’s head that looked like it had survived a week-long hibernation without a brush. I half-jokingly suggested throwing on a hat and grabbing Chipotle anyway.

That didn’t land. I was called an asshole, accused somehow of being responsible for the knot, and just like that — curtain closed. I wished her well, blocked the number, and sat there wondering if dating had always been this strange or if I’d simply forgotten.

So which came first — the jerks or the chaos?
Maybe neither. Maybe it’s just two people missing each other’s tone through a screen.

Either way, the whole experience reminded me of something simple: every friend you have today was once a stranger. Some strangers stay. Some drift off after shaved ice. And some disappear over a hair knot before Chipotle even enters the picture.

But the point is to keep showing up, because connection — even the awkward, imperfect kind — is still worth the try.

(Not actual pic of her hair…)