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You showed up. That's already gutsy. Now here's how to turn the person next to you into someone you'll remember.
For solo traveller meetups, everywhere in the world
The real problem
It's that most questions are boring. Not because you're boring, but because we were never taught which questions actually open a conversation, and which ones just close it politely.
You know the feeling. Someone asks "what do you do?" and within 30 seconds you're both nodding at each other with nothing left to say. That's not chemistry, that's a bad question.
The good news? One better question changes everything. Here's how to find it.
The framework
Think of every question as either static or signal. Static gives you facts. Signal gives you stories, and stories are where real connection lives.
Static, closes fast
Signal, opens everything
You don't need to overhaul how you talk. You just need to swap two or three static questions for signal ones. That's it.
The swaps
Here are the three most common conversation-killers, and the Just Gutsy version that actually goes somewhere.
Swap 1
"Where are you from" gets you a country. This question gets you a story about a place, a feeling, maybe a whole chapter of someone's life. It also works just as well for people who've never left their city as for nomads who haven't had a fixed address in years.
Swap 2
Job titles are costumes. What someone is obsessed with, whether it's fermentation, open-water swimming, or figuring out how to speak to their mother, tells you who they actually are. Fair warning: this one gets deep fast.
Swap 3
Duration is logistics. The "why right now" is always a story. Sometimes it's a breakup. Sometimes it's a promotion. Sometimes it's "I just needed to go somewhere." Every answer is a door, walk through it.
The rhythm
You don't need to go deep immediately. Good conversations move the way good travel does, you start at the airport, you get to the neighbourhood, then you find the hidden spot no guidebook mentions. Same thing here.
The Landing, easy in, no pressure
Start light. Shared context, light observations, anything that says "I'm here, I'm friendly, I'm curious." You're both standing in the same city, probably lost in the same beautiful way. Use it.
"What's the first thing you did when you arrived here?"The Turn, shift from info to story
This is where most conversations stay forever. The Turn is simple: stop asking for facts, start asking for moments. One word swap changes everything: "what" → "what surprised you about..."
"What's something about this trip you didn't expect?"The Depth, where it gets real
Only go here once there's some warmth. And when you do, don't rush to fill the silence. The best answers take a second to arrive. Let them.
"What do you think you're really looking for on this trip?"The Just Gutsy game
21 questions. Three levels. No rules except one: if you answer, you have to mean it. Pick a level, pick a question, and see where it goes. The best conversations at solo traveller meetups have started with one of these.
Tap a level to reveal the questions, use them in any order, mix and match, or just let them inspire your own.
Taking these to a meetup?
Just Gutsy 🌍
A global community for solo travelers who believe that real connections make the best memories.
Now on iOS & Android
Free to download. Meetups around the world. Real people, real trips.
For anyone ready to take the leap.