Lessons From a 1997 Chatroom: What Online Weirdos Always Knew About Emotional Marketing

It was 1997.

I was in a Yahoo! chatroom - wearing platform sandals, drinking a Clearly Canadian, probably quoting Charmed...when I met a boy.

Not on Bumble. Not with filters. In a chatroom. A glitchy, dial-up, /follow type of chatroom.

That boy? Now my husband. (Hi, Drew Barbee .)

Back then, telling people you met someone online was enough to make them gasp. Or judge. Or tell you to “be careful” because “that could be a serial killer.”

Now? That’s just called Tuesday.

But even in that ancient corner of the internet, something powerful was happening. And it’s something every modern marketer still forgets:

Real connection doesn’t require perfect lighting. It requires emotional presence.

Which means? A lot of the old-school internet weirdos like me were learning brand loyalty skills before we ever had a business card.

Here’s what I learned in that digital time capsule—and why it still works now.

💬 1. Curiosity Is Still the Entry Point

In the ‘90s, nobody joined a chatroom hoping to be pitched a product. We logged in because we were curious. Bored. Lonely. Looking to feel seen.

Guess what your audience is doing today?

They’re not doom-scrolling LinkedIn to find your CTA. They’re hoping something resonates.

If your brand doesn’t spark curiosity—if you’re not giving people a reason to lean in, explore, or feel something—you’re just static in the feed.

TIP: Start conversations your audience actually wants to finish. Don’t lead with what you sell. Lead with what you see. Talk about them before you talk about you.

🧠 2. Vibe > Visuals

In that early chatroom, we didn’t have photos or videos. Just usernames, awkward fonts, and raw emotion typed out in real time.

Which meant every sentence mattered.

There were no filters. No carousels. No content calendars. It was just… vibe. You had to mean it.

And that’s exactly what makes today’s best brands magnetic. They don’t just broadcast. They feel like someone you’d want to stay up late chatting with.

TIP: Audit your captions and emails. Would you read them if you weren’t being paid to? Does your copy sound like a pitch, or a person? Ditch the robotic marketing voice. Embrace emotional clarity.

❤️ 3. Relationships Are Built in the DMs, Not the Launch

When Drew and I started talking online, we weren’t trying to get somewhere. We were building trust in small moments—jokes, confessions, late-night chats.

That’s how loyalty is built in tourism, too. Not in your shiny launch. Not in your glossy video.

In the micro-moments.

In the hidden touchpoints that see the guest—even when they’re not buying yet. The Lyft ride, the Airbnb coffee table, the Instagram comment you actually responded to. That’s what they remember.

TIP: Map your “unseen” touchpoints. What’s the emotional experience of arriving at your destination? What do your comments, autoresponders, or STR hosts say when no one's watching? You’re either earning trust—or proving indifference.

Let’s Stop Acting Like Connection is a Trend

The best campaigns don’t need the algorithm’s permission. They just need to make people feel like they matter.

That’s what a 1997 chatroom taught me. That’s what ICQ, AIM, LiveJournal, and every other digital love note was really about.

So yeah, I may have met my husband in a way that once made people cringe. But that “cringe” was just early access to the emotional economy.

And if your brand still thinks connection is optional? You're being outplayed by teenagers with dial-up.

See ya on the flip side,

Jenn

P.S. Let’s bring back Clearly Canadian, dial-up patience, and chatrooms that didn’t spy on us.

P.P.S. The original “DM me” was an ICQ uh-oh! at 2 a.m.