The Art of Asking Better Questions When Travelling (And Even When You’re Not)

Imagine if you had the exact same conversation with every single person you met for the next 6 months. Doesn’t that sound absolutely awful? It’s boring and repetitive and meaningless and it just drives you crazy.

The thing is, this actually happens when you go travelling. I mean, sure, I’m exaggerating a tiny bit – it’s not every single person you meet, and it’s not exactly the same conversation, but it does come very, very close:

Where are you from? How long have you been travelling? Where have you been? Where are you going next?

This might not sound too bad, but I know when I was travelling I would get asked this by almost everyone I came into contact with: shopkeepers, other travellers, taxi drivers, fellow passengers on various modes of public transport….. and I hated it.

There are so many reasons not to start a conversation with these questions, but the simplest one is this – whoever you’re asking has almost certainly been asked this about a million times before. I don’t know about everyone else, but I get small talk fatigue. Or I suppose more appropriately I should call it ‘shitty repetitive question’ fatigue.

I’m always tempted to just type out the answers to those questions and hand out my responses to anyone who asks. Sounds harsh? Maybe, but when you’re doing long term travel, you meet about 10 new people a day (at a very conservative estimate). If you’re travelling for 6 months, that’s something like 1800 times that you have to say pretty much the same thing!!!


That is not why people travel. One of the things I love most about travelling is those deep connections you forge with the people you meet, and the profound and meaningful conversations you get to have with them – conversations that challenge your opinions and broaden your perspective and that genuinely change and augment your experience. You want to cut the boring shit and get straight to the bits that will really tell you who the other person is.

This is a really easy way to differentiate between well-seasoned travellers and noobs – although I also use it to judge who’s interesting and worth talking to and who I’m going to ignore. I realise that sounds mean, but I hate wasting time, so I usually just smile and say I have to run off somewhere – or I go ahead and call them on it.

Is that really the best thing you can come up with? I’ve been asked that question so many times today and I’m sick of answering it. Isn’t there anything else more interesting that you’d like to talk about? I was a cheerleader for a little while, want me to tell you about what that was like?

Here’s the thing – it’s not hard to have a better conversation. Think about things that you miss talking about with your friends back home, about the books you’ve been reading while travelling, about the shoes the other person’s wearing that you think look great/awful/strange, about whether there’s any good Thai food in the city…. there’s an endless list of conversation starters that I can absolutely guarantee you will get a more enthusiastic response than those generic questions.


It’s not contrived either, it’s just being thoughtful, and it can lead to some wonderful shared experiences. I mean, imagine your conversation went like this:

Hey, I’m Des, I just got here and I’m super hungry – do you know if there’s any good Thai food around? Or a decent supermarket? I’m kind of thinking of cooking but I’m still trying to decide if I’m too lazy and impatient or if I should try to stave my cravings and save some moolah.

When I was in Serbia, I went up to this bunch of guys to ask them for food ideas and it turned out that they’d cooked up a huge heap of Mexican food – way more than they could eat – so I ended up sharing their (incredibly delicious) dinner instead and then chatting all night about jazz music and medicines and Eastern European animal sanctuaries that you could volunteer at.

And if you still want to know the answer to those generic questions, just slip them in topically. These things do naturally come out when you’ve been talking to someone for a while. Like in that conversation in Serbia, we all told each other where we were from when we compared health services in our home countries, and we told each other how long we’d been travelling when we were talking about health insurance.


So next time you pack your bags and run off – or come across someone else who’s travelling – think before you ask them obvious questions. Remember, here is someone from a completely different world with amazing stories to tell and experiences to share – someone who will probably be passionate and funny and abundantly interesting if you just give them the chance. Don’t ruin it by being a lazy bore.


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