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10 Icebreaker Questions That Can Lead to Deeper Travel Relationships

Wellness Romance
by Georgina Guthrie Oct 29, 2019

Meeting fascinating people is one of the best things about traveling, but it takes time to develop a relationship — and that’s something you might not have a lot of if you’re on the road. The good thing about icebreakers is they can help you build rapport with strangers faster.

The best questions are original, or at least unusual. Greeting someone new with “how long have you been here” and “where next” is okay, but these openers can lead to some pretty repetitive conversation patterns because people use them all the time. It also leads the other person down an all-too-familiar route. Instead of using the same greetings as everyone else, take the plunge and offer a question that gives your new friend permission to open up in ways they haven’t done before. Asking something they aren’t expecting means you’ll get better thought-out answers, which keeps their energy level high and helps you work out if there’s chemistry.

So, next time you’re waiting for a late ferry or train, don’t let the opportunity pass you by. Strike up a conversation and try these 10 icebreaker questions for size. You might end up with a new friend for life.

1. What inspired you to visit [insert country]?

This is so much better than “how long are you here for?” which is what’s known as a closed-ended question (something that only has a one-word response and can’t go anywhere else). Instead, try asking your new friend what inspires them. This reveals more about their personality and it allows them to share their values or hobbies. It also gives you the opportunity to respond with your own personal details, which helps build closeness and trust.

2. How do you spend your time when you’re not traveling?

Asking someone about their day job could result in a fascinating response, but let’s be honest — the chances of you meeting a volcanologist versus an admin assistant are a million to one. Plus, if you get the latter (or similar), feigning interest will come across as disingenuous — and you’ll both know it. Some people don’t see their own jobs as particularly interesting and would much rather discuss what they do for fun, so instead, keep the question open-ended and let them decide what to share. That admin assistant might also be an amateur drag queen. If you’d focused on their job, you’d have missed out on this conversational gold.

3. What brought you here?

This is a no-pressure way to invite someone to discuss their personal life before they came traveling. Rather than diving straight in with “what did you do before you came here?” you’re leaving it up to them as to how much they share about their past. People travel for a multitude of different reasons — most of which are positive, but some not so (break-ups, redundancy, and a family bereavement are common stories you’ll encounter on the road). Keep your questions as open-ended as possible, and let the other person elaborate at their own speed.

4. What are you looking forward to next?

This is better than “where are you headed to next?” which usually results in a closed, one-answer reply. Asking about upcoming plans is a much broader question, and could include both a destination, as well as timeframes, activities, routes, and motivations. This keeps the conversation flowing and gives you a segue into sharing your own travel or activity tips with them. It’s also focused on anticipated joy, which instantly takes them to a happy place, keeping the talk high-energy and positive. And if they reply with “nothing,” then take it as a hint to move on.

5. If you could describe your week in a movie title, what would it be?

Asking “How’s your week been so far?” is okay, but the other person will usually respond with “pretty good” or something equally noncommittal. Why? Because this type of question, along with “how’s it going?” is considered more of a formality than a genuine request for information. Asking your new pal to describe their week with a movie title (or book, song title or emoji — your call) encourages them to really think about their week more specifically and have fun with their answer. They’ll also want to explain their choice, which opens the doors to more conversation.

6. If you could pick a day to relive, which one would you choose?

There are variations on this question, like “what’s been your favorite moment so far” or “what’s been your favorite place,” but phrasing it like this is more unusual, which encourages the other person to really consider their answer. It also means you get to hear more about what really matters to your new friend.

7. Where did you grow up?

This potent question packs way more punch than “where are you from” because it invites the other person to give you a mini autobiography and share as much or as little of their life with you as they want. People usually consider growing up a long process and will likely mention several places, milestones, and events — which is way more interesting than hearing (or talking) about a literal birth location.

8. Is there anything you need help with right now?

This is always a surprising and disarming question to be asked — especially if they’re not outwardly displaying any signs of distress or need. When questioned, people often realize there is something they could use a hand with after all, whether that’s you keeping an eye on their bags while they pop to the loo, some travel tips, or just someone to share a taxi with. When we help people out, we instantly build a level of trust — so asking this question is your shortcut to making that deeper connection.

9. What’s the strangest icebreaker question you’ve ever been asked?

This is a good one because you’re piggybacking off someone else’s work. You encourage the other person to share a weird event and you get to hear their response. It also means you get to answer the question yourself (if you want to) or upstage it with a weirder one.

10. What’s your favorite way to travel?

Once, I got into a conversation with a guy who told me all about a ten-hour train ride he went on in India. The long and short of it was, he took some opium (we don’t recommend this) then succumbed to an explosive bout of food poisoning, all while crammed into a tiny carriage. Needless to say, his anecdote was horrifying and hilarious in equal measures. I’ve also met someone who was held up at gunpoint on a bus and another person who’s been in a shipwreck. Some of the most entertaining, heartwarming, and fascinating travel stories involve transport — and this deceptively simple question is your ticket to potentially hearing one of these tales.

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