Stranger Encounters – How to Meet People

“Stranger Encounters” is a segment on how I met someone  new recently. Take what you like from my experience to learn how to meet people, in real life. 



April 13, 2023

While preparing to start our hike of Ha Ling Peak in Canmore, Alberta, a man approached us and asked if we were about to hike it. We told him that “yes”, we were. He asked if we had done it before, to which we replied, “yes” again. 

And then to my surprise, he asked, “Can we hike with you?” Again, we said, “yes”. This was a real pleasure for me, as I am typically the person who goes up and meets new people. It was neat to be on the receiving end. I must admit, that when Chris first approached us, I was a little hesitant. A thought went through my mind of, “What does this person want from me?” Thankfully that concern lasted less than two seconds, so I was prepared to say “yes” immediately when he asked if we could hike together. But this reminded me of how many people get stuck in that negative mindset. And that’s a shame as almost everyone I meet are very pleasant people.

That’s how I met Chris and his cousin, Mark, and friend, Trevor. They were on a day off after a busy week of work in Calgary and are out on a work project from Ontario. 

We hiked the first 2/3 of the mountain with them, met them at the top and then saw them after the hike as I offered to drop off their rental equipment in the morning. While at our place, we shared more laughs and then there was a spontaneous glow in the dark juggling show. I tol

d them that this is the prize for being open to meeting strangers. 

Mike shared a great story of how he met another Rasta in a grocery store in Jamaica, and then before he knew it, they were having a meal together and he even scored a great place to stay.

It was a joy to meet these three people who were new to hiking on this beautiful, snowy April day. 

April 3, 2023

Vee and Nic from the travellers network, stayed in our home for two nights and we had a lovely time together sharing stories, food, time in nature and life. See the video below for a short interview. 

March 24, 2023

When I saw the bicycle with the trailer parked outside the Safeway, I suspected that I might bump into another cyclist. Once I came out of the store, I was not disappointed.

That’s when I met the very well known, local legend, Crazy Larry. I said hello by asking which direction he was going and he went right into a whole bunch of stories. We probably talked for about 15 minutes and it was really joyful.

One of the things that I love the most about our visit, was how many people said hello to him by name as we stood outside talking. He also told me that he is very well known locally and I see this as evidence of someone who has a very rich life. Feeling connected to people is one way we can literally extend our lives. Check out the research on the link in my bio if you are curious. 

Connect with people. It’s good for you and good for them.

March 23, 2023

While listening to the excellent music of Mr Bird, I overheard Chelsea and Andy talking about how to say something in Russian. As I lived in Russian speaking countries for about two years, I understand a bit of the language, so I used this as my excuse to say hello. I approached them by saying, “I just overheard you speaking about the Russian language?” And by saying that, I was very warmly invited into the conversation. I’m sure it didn’t hurt that they had likely already had a drink or two, and the interaction was fun and pleasant. 


Feb 14, 2023

As part of the “Human Connection Challenge” by Dr. Caroline Brookfield, I had to meet a stranger and the theme for today was, “Novelty”. Her suggestion was to read something that we would normally scroll past, and then to use that as a way to connect with someone else. 

So I went skating on the pond in Canmore. I noticed myself feeling a bit nervous at the idea of having to speak to a stranger, even though I love meeting people and have had almost entirely positive experiences from intentionally meeting over 3000 strangers (outside of my work) over the years. 

I decided to approach two skaters who had stopped skating but were still on the ice, and this is how I approach them. “Excuse me, have you heard of ChatGPT?” In French accents, they both replied, “No”. I explained that it’s AI technology that is very popular on the internet now to which the man replied, “I don’t really spend much time on computers.” And then I said, “That’s awesome!” I encourage people to meet people in the real world.

From here, we easily had a great conversation. I decided to invite them to an upcoming in-person gathering that I’ll host on March 2nd and he gave me his email address as we live in the same part of Canmore. 

This was really uplifting for me and I hope to see Gwen again soon. Thanks for the challenge.

Day 2 Complete.

February 13, 2023 

I was in my hometown of London, Ontario, Canada, waiting to board my flight. As I listened to a captivating webinar about AI, I overheard the people in front of me discussing the ease of flying out of London compared to Toronto’s Pearson Airport. I joined the conversation since I could relate to their experience and shared my own thoughts about flying out of London. This led to a pleasant conversation with one of the men, as we boarded the plane. He shared his recent flight cancellation experience, and I listened attentively. This experience of starting a conversation with a stranger came naturally and didn’t take up any extra time. It happened because I was being present. 

If you have a structured and predictable life, it may be helpful to consider adding something new, such as a new activity or sport, or letting go of something that doesn’t fulfill you. Additionally, consider the opportunities around you to practice Talk2MorePeople Listening. This intentional and respectful overhearing of conversations can lead to chances to join and contribute to them. Remember, such opportunities require intention rather than time. (For more information, see page 17 of the T2MP book.)

You can get your free copy of the Talk2MorePeople book at

Feb 12, 2023

It was such a treat to have met Rich on this day. At the time, I was traveling with another stranger, Caleb, whom I met through the ride-sharing app, “Poparide” Rich approached the vehicle and held up a card explaining that he was deaf. I read this, and we gave him $5. This was followed by a really enjoyable interaction. I also greatly enjoyed the conversation that I had with my ride-share guest, Caleb. Connecting with strangers is so important. Below is a link to a recent podcast on what the research currently says about how these small interactions with strangers can actually help you with your mental AND physical health! This is the podcast where the researcher who I cite in the Talk2MorePeople book, Dr. Gillian Sandstrom, speaks with the founder of the GEN Well Project, Pete Bombaci. They discuss the mental and physical health benefits from connecting with people and also touch on the national social connection guidelines that are being developed in Canada. Exciting stuff! The Current on CBC:…


February 25, 2023 at the Emerald Lake Lodge

My partner and I recently stayed at the Emerald Lake Lodge to celebrate both of our birthdays. While on the shuttle to the cabins, we met Rob and Terry. They were on their way to visit family in Calgary and stopped to spend a couple of nights here. Rob had photography equipment so I asked him about it. He told me that he’s been a professional photographer for much of his life. He kindly gave me his card and invited me to check out his website.

I’m sure glad that I did! Based in Nelson, BC, Rob’s photography is simply stunning. You can see it HERE. (and see one of his photos above).

We also got to visit with them as well all walked to our cabins together down a beautiful, snowy small road. This place is magical in the winter time. You can check out my 360 video playlist from that day HERE.

We’ve been in touch by email since meeting then. I don’t know if I’ll see these kind people again or not at this time, but I remember feeling warmed at the opportunity to check out his work and to stay in touch. This was a reminder to me of what the research says about the importance of connecting with people – it’s good for our moods. It’s good for us.

And, you never know. Maybe we will meet again one day.

It was lovely to have met you Rob and Terry!

The photo below was sent to me by Rob.

February 8, 2023 at Gibbons Park, London, Ontario

Today, met Gary bishop in Gibbons Park. He had a huge lens on one of the two cameras that were wrapped around his neck and I met him by asking, “What are you shooting today?”

I was just curious.

This lead us into a really enjoyable conversation for about 10 minutes about the animals in this park. He let us know about a family of owls. I was there with my mother and she was so happy to have met someone new. Check out our experience in the VIDEO below. Meeting people is good for you. Get out there and Talk2MorePeople.

July 20th, 2022 at Mt. Nelson Athletic Park, Invermere, BC

On this  morning in Invermere, British Columbia, I met David, his wife Jennie, and their children in the park pictured above. I enjoyed watching the family play a game of Ultimate Frisbee while having my morning coffee on a park bench. It was fun to witness this family play together and to hear the parents competitive sides come out. I used to play Ultimate Frisbee so that was the excuse that I used to say hello to them.

I approached them by saying, “Hello. I just wanted to say that I enjoyed seeing you play Ultimate Frisbee because I used to play Ultimate.”

Notice how I didn’t sit and try to scheme something clever to say, but rather, I pretty much just explained what I observed as my ice-breaker. I did consider that they might not want to hear from me – a total stranger – but I know from experience and from the research that I likely wouldn’t get rejected.

And this lead into a really enjoyable conversation.

They shared how as parents they are happy to play two-on-two Ultimate with two of their three children.

We also talked about van-camping as my partner and I had slept in our camperized van on a random street the night before. Their family is considering doing so in the future as well so David in particular had lots of questions for me. On this subject, we had what I call an “Information Gift-Exchange”. You can read about this concept in the Talk2MorePeople book.

I gave David a Talk2MorePeople sticker that has my contact information on the back. He told me a story about how he met one of his best friends eight years ago while walking with his young daughter. In that instance he invited the stranger over to his house for a barbeque and they have become lifelong friends.

Often when I meet new people, I invite them to remain in contact with me by giving them a sticker. When I do this, it’s always so enjoyable to hear how often people share their stories with me about how meeting a stranger once changed their lives.

I’m grateful for this enjoyable conversation and to have met them. It brightened up my already sunny morning. You can use your simple observations to connect with new people and you may very well be surprised just how well those conversations can go.


Tony Esteves is a virtual and in-person Business Coach for Artists, author, facilitator, and circus performer living in beautiful Canmore, Alberta, Canada. With over a decade of coaching experience, he has helped many individuals and businesses achieve their goals. Tony is a passionate adventurer and has traveled to 40 countries, believing that adventure is an essential aspect of living a full life.

In addition to coaching, Tony is also an experienced facilitator who has led in-person learning experiences in Canada, the USA, South Africa, South America, Europe, and Japan. His mission on this planet is to bring people together and create more human connections.

Tony is the author of “Talk2MorePeople: Change Your Life by Meeting People,” which teaches people to uncover opportunities and adventures by putting down their phones and connecting with real, live people face-to-face. By registering for Tony’s free “Talk2MorePeople Tips” at, you will receive a FREE Human Connection Starter Kit including more than 80 different ways to meet new people. Learn how to build more human connections into your life and business today!