How to Start a Conversation When Travelling Solo

by | May 15, 2020

how to start a conversation when travelling solo
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Last updated on April 30th, 2023

How to start a conversation and get curious  

by Amanda Burgess, Contributor

Think about the most colourful and meaningful conversations you’ve had on your travels. They likely started with a question based in curiosity versus polite small talk. To help you feel more comfortable when it comes to the age-old question of ‘how to start a conversation when travelling solo’? we’ve compiled some deep, interesting conversation starters that you can take with you on your next travel adventure – or use right now to deepen the existing relationships in your life.

These conversation starters are answered by our team, but feel free to share your answers to any of these or add to our list with your best get-to-know-you questions in the comments. There’s no shortage of interesting questions or ways to connect with people on a deeper level when we travel solo.

Eight questions to ask to start a conversation when travelling solo

1. What would be your first question after waking up from being cryogenically frozen for 100 years?

Answered by Melissa Fox, Webmistress

“Where’s the bathroom?”

Kidding – that’s a nod to one of my all-time favourite TV series, Futurama. The lead character, Fry, is accidentally frozen for 1,000 years, not 100, however.

If the rapid rate of change over the last 30-something years I’ve existed in this world is any indication, I expect life to be dramatically different in 100 years. Floating cars? Implanted devices that allow you to send and receive calls or emails with the mere blink of an eye? Virtual surgery? Robots in every home? Not outside the scope of reason, if you ask me.

Taking that into consideration, I think I’d be most curious about the state of my island home, Bermuda. Has it disappeared back into the Atlantic? What’s the political atmosphere? How much are flights and is it still prohibitively expensive to live and vacation there? Can I get a fish sandwich on raisin bread with coleslaw at Art Mel’s?

2. What chance encounter changed your life forever?

Answered by Tom Zara, Strategic Partnerships

Like so many of my circle of friends, we lived a privileged and sheltered adolescence until I ventured into the real world as a freshly minted college graduate. The globetrotting experience expanded by an understanding of art, history, architecture, diversity and cultures but it wasn’t until I entered the slums of Calcutta that my understanding of human resiliency and dignity revealed a profoundly altered meaning.

The accidental discovery of a vast expanse of urban Indian life was greeted with an affluent perception that teeming poverty meant squalor, disease, hunger and all forms of depravity. How utterly corrupt were my expectations. Instead, I was invited by the warm smiles of curious children, allowed to wander among the groups of women sharing stories, cooking communal meals and minding the care of restless children. Everywhere I looked men were busy managing all forms of commerce from selling vibrant coloured fabrics, to exotic fresh fruit, and sandals made from car tires. This was a safe, thriving community steeped in the ability to make the most of life even when blessed with the least.

Calcutta taught me a life lesson that humans can find hope under the most austere circumstances, seemingly grateful for the gift of life and the strength of community. While so many are void of basic necessities, I’ve grown to learn that perseverance, ingenuity, faith and family shield the vulnerable and are the strengths that invite optimism and slays despair.

3. What’s the most heartwarming thing you’ve ever seen?

Answered by Amanda Burgess, Contributor

Last spring, I challenged myself to slow down the breakneck pace of my life to play tourist in my own city of Toronto. Something I recommend for anyone in a city still under lockdown to try. I walked everywhere.

One day, while waiting at a crosswalk, my eye was drawn to a young boy of around 10 trying to get his little sister, around five or six, to move on from where she’d stopped at a flowering bush. I smiled, amused as only one who has a sibling or has raised some can be. When his sister refused to move on, pointing up at a pretty pink bud far beyond her reach, this young boy didn’t get annoyed or hurry her on. He stopped, turned, and walked over to stand beside her.

Watercolour illustration of cherry blossoms

He looked up at the bud. Looked down and smiled into her face as she stared up into his with hope colouring hers. I watched as he stretched up on his tippy toes, plucked the bud, and handed it to her. Watched her face bloom into delight. The entire exchange probably spanned about 40 seconds — one of those moments where time appears to slow down so you can appreciate what’s unfolding in front of you. But this act of love from a little boy — beautiful inside and out — and the happiness it inspired in me to have witnessed it stayed with me. Whether in your own city or on your travels, I invite you to slow down. Stay rooted in the moment. Keep your eyes open for the stories playing out around you. Write them down and retell them. Anything that warms your heart is meant to be shared.

4. How different was your life one year ago? 10 years ago?

Answered by Melissa Fox, Webmistress

Without the influence and opportunities provided to me by women like Evelyn, Erica and Carolyn, my life today would probably be quite similar to one year ago.

Then, my career was up in the air. I was still working remotely, but for a software start-up and only part-time. The rest of my time was dedicated to raising my soon-to-be-one-year-old and shuttling my just-turned-five-year-old back and forth to kindergarten. I was trying to figure out how to get through each day, the prospect of anything more was beyond my exhausted mind.

Ten years ago, I was even less ambitious, sharing a one-bedroom basement with my best friend, working a retail job I was woefully unhappy with, and living paycheque to paycheque. The concept of owning my own business not even a thought on the horizon. I did meet interesting and amazing people, and I had my fair share of experiences that I’ll never forget. While I’d never go back, it did lay the groundwork for my passion for content creation and development.

In 2013, I was introduced to Evelyn and, with no experience in what she required, she decided to take a chance on me. It has been the most incredible learning curve, with a huge boost since the equally inimitable Carolyn took the reins of JourneyWoman. At first, I was afraid (I was petrified). I have been involved in website takeovers, and they usually turn quite ugly. Carolyn has put all my fears to rest, and not only do I get to continue working on a project that is so near and dear to me, but it has also been the most empowering experience, and I can quite honestly say that I have changed more in the past 8 or 9 months working on this team then I have in the last decade.

5. What book has had the biggest impact on you?

Answered by Carolyn Ray, Editor

Books have always been my refuge. I’ve been a bookworm since I could hold a book, thanks to my grandmother, a former teacher who cultivated my imagination from a young age. In my teens, I was incredibly introverted, shy to a fault and the skinniest, nerdiest kid ever! Whenever I would visit her house, I would run upstairs to my bedroom and escape into a new hardcover book waiting for me: Jane Eyre, Jalna, Tess of the Ubervilles, Nancy Drew, Rebecca of Sunnybrook Farm and so many more. Looking back, I now see my nana was feeding me lovely stories of courageous young women at a time when I desperately needed to find some essence of bravery within myself.

When I separated from my husband at age 34, books again saved me. I was desperate to find women like me, women who were raising a child on their own, women who were trying to hold down full-time jobs and manage a household alone. I searched for inspiration everywhere and found it in Maya Angelou (everything she wrote), Leap of Faith by Queen Noor, The Red Tent by Anita Diamant and Marianne Williamson’s A Return to Love. Then, I discovered historical fiction and my travel journeys became deeper and more meaningful. Phillipa Gregory, Paula McLain, Karen Harper, Alison Weir, and so forth.

When my daughter became a teenager, I haunted bookstores looking for the hardcover books I’d loved as a child and eagerly bestowed them on her. There’s something about holding a worn, tattered book, and touching the crinkly pages that you just can’t get from a glossy reprint. As Anne Lamont wisely says: “For some of us, books are as important as almost anything else on earth. What a miracle it is that out of these small, flat, rigid squares of paper unfolds world after world after world, worlds that sing to you, comfort and quiet or excite you. Books help us understand who we are and how we are to behave. They show us what community and friendship mean; they show us how to live and die.

6. What’s something that took you out of your comfort zone?

Answered by Amanda Burgess, JourneyWoman Editor

The ones that ignite twin flames of fear and fascination in your belly. The ones where you hear the voice of your intuition whisper: “Do it. Go. Don’t think. Don’t analyze. Just do.” I felt that burn in 2013 when my late husband’s mother – a passionate teacher – passed away and left us a tidy sum to build a school in a developing country where girls, in particular, would benefit from education. We were plagued with fears and doubts at all the risks of an undertaking like this one. What if we chose the wrong organization to work with? What if instability in the chosen country led to the destruction or dismantling of the school, erasing her legacy? What if the people of the community didn’t want or appreciate our interference?

But the call to carry out a woman’s lifelong dream was strong, so we put those fears and real risks aside and let our hearts guide us to imagine1day (now part of WE) and the tiny village of Gobele, Ethiopia. And in 2014, when we attended the inauguration. We heard community elders explain just what the school meant for their village. We heard from a young mother in Grade 4 with a baby strapped to her back, who told us how inspired she was by Sharyn’s story before reading us a poem she hoped would inspire other married women with children to return to school.

By the time we visited again only two years later, so much had changed for girls and women in Gobele with our sustained fundraising and investment. We expanded the capacity of the school from 400 students to 750. Girls enrolment had increased from 60 to 182, closing the gender gap (boys enrolment sat at 302). 101 adult students were attending literacy classes, 91 of them women. Gobele became a hotbed for women’s rights, with signs around the grounds boldly making the community’s stance on several issues known.

Big risks should scare you. But pay attention when they also thrill you. With great risk often comes great reward.


7. What small gesture from a stranger made a big impact on you?

Answered by Tom Zara, Strategic Partnerships

Many years ago while backpacking across Asia I fund myself meandering the dusty and noisy streets of Tehran in search of the Mirror Hall in the Golestan Palace to marvel the Faberge Eggs collected by The Shah of Iran. As an American, I was keenly aware of the political fervour and did everything I could to mask my identity in favour of anonymity. That was until I met an 8-year-old boy who was relentless in his insistence that I follow his lead.

With some healthy apprehension, I obeyed his gestures of encouragement and soon arrived at a walled courtyard in the heart of the capitol. As I entered I was welcomed by a chorus of children eager to show me their school, proud that they were learning and practicing English and appreciating the joy of education. Their enthusiasm for learning and curiosity towards strangers has played again and again throughout my entire life. The universal innocence of children reminds us that we have the innate capacity to connect and to share what is common to us all.

8. What is your spirit animal?

Answered by Carolyn Ray, Editor

I was born in Toronto, but I grew up in Florida, so I tend to associate with all things water. I’d like to say that my spirit animal is something fierce like a tiger or a bear – but I’m a water girl, so I think it’s probably a turtle.

There’s nothing that brings me more joy than seeing a turtle gain speed and agility in the water, how they glide fearlessly through the sea, ignoring what evils may lie beneath. As I get older, I want to play more – and embrace the silly and ridiculous – and I think a turtle brings me closer to that. I would imagine that a turtle just goes with whatever way the current is moving, flitting among all the other species.

What other conversation starters do you use when you’re travelling solo? Share them in the comments below. 

sea turtle

Amanda Burgess is a Toronto-based writer and creative strategist whose bags are always packed for her next adventure. She is a Certified Cancer Journey Coach who creates a safe space for cancer patients and caregivers to design their dream lives – while living with cancer, and on the other side of it. Amanda freelanced for JourneyWoman until December 2021.


We always strive to use real photos from our own adventures, provided by the guest writer or from our personal travels. However, in some cases, due to photo quality, we must use stock photography. If you have any questions about the photography please let us know.

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