Do You Believe People Are Strange? Developing the skills for conversation with strangers

The skills and attitude that help foster more meaningful connections with strangers

I don’t know about you, but I’m saddened when I see people sitting at a restaurant table and everyone has their eyes on their phone. I’ve seen couples where both are glued to their phones. It even happens in group gatherings. When we’re walking down the street, one of the hazards of modern life is having to avoid a pedestrian who is reading his/her mobile. Of course, sometimes, it’s a bit more justifiable (i.e. checking directions). But more often than not, it’s watching some video or reading some message. In any event, it’s another instance of people retracting from the real world around them. I have to admit that I can be guilty of doing the same. It’s something I have to fight against. The other tragedy of our times is the lack of interaction in the streets with strangers. Pretty much all the time, as we err outside, we’re in our own bubbles, ignoring the lives, faces and emotions of passing people. Yet, when I’ve gone out of my way to engage, it’s virtually always rewarding. If we don’t practice speaking with those we don’t know, we’ll lose our ability to meet and, more saliently, lose a chance to learn and expand our horizons. My desire is to encourage you to go seek out a stranger and start up a conversation. Let’s re-engage with one another without the security of knowing what everyone thinks and feels. The more you do it, the easier it becomes.

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In the early days of the pandemic, after the first lockdowns had begun, I made a startling encounter. With claustrophobia setting in, I went for a walk in the communal garden. The sun was bright, but there was a nip in the air. As I walked by a park bench, I saw an elderly lady sitting alone with her walking sticks to the side. She was just looking up at the sky. Passing in front of her, I wished her a good day.

“What’s that you said?” she quickly fired back. “I’m hard of hearing.”

“I was just commenting on how lovely a day it was,” I replied, now standing in front of her.

“Crazy days,” she murmured.

“Ah, yes, that’s true,” I intoned.

“What did you say?” she asked again. “Won’t you please come closer?”

I was hesitant since this was an elderly lady and by all accounts frail. According to government policy and, following the news about who was truly vulnerable to Covid, I was supposed to keep my distance.

“Come and sit down here,” she continued, putting her hand out on the empty space on the bench.

And thus began a 15-minute first encounter with 96-year-old Doris. We very quickly started discussing the ongoing brouhaha. I had to make sure she was aware of the risks, which she promptly brushed aside with a phrase that has stuck with me, ever since: “You know, young man, I’d rather die living than live dead.” Putting aside the compliment (I’m nearly sixty years old), what Doris proceeded to describe was a reminder of what is true hardship, with an uncanny ability to put things into perspective. Doris told me about her experiences in WWII, where her husband went off to war while she worked humongous hours in the War Office, then her house was bombed and they had to live in the Underground, and then her beloved father died because his weak lungs couldn’t handle the dank and dusty living conditions. “Yes,” she reminisced, “those were difficult days.” In short order, Doris set the record straight. Over the course of the next fifteen months, Doris and I became friends. She had been extremely lonesome, as no one was technically allowed to visit her. With her poor hearing, old-fashioned telephone calls were hardly satisfactory. So, with her unfettered approval, I decided to visit her regularly, albeit clandestinely. She systematically got herself dolled up for our visits and talked about how she felt alive, although always ready for the end. It reminded me of the philosophy behind The Grateful Dead, a band I’ve been enamored with all of my adult life: Once you accept your finitude, you become ever more grateful for every day of your existence.

Connected yet so disconnected

It’s evident that for as much as we all rely on our phones and feel plugged in, we have never felt so detached. If you search on Google for the combination of words with this query: “connected but disconnected” (see below) or “connected yet disconnected,” you’ll see just how many people have written about this paradox.

Figure 1 - Google search query results Nov 1, 2022

We’re clearly heavily dependent on the Internet, and as the younger generations grow up, our use of digital devices is only going to increase. The amount of time and number of times that we do our online activities via a mobile is inexorably rising. It goes with us everywhere. A 2018 study by RescueTime showed that its users on average were spending 3 hours 15 minutes on their mobile every day, consulting their phone on average 58 times daily. A more recent study from Statista, in 2021, showed that the average amount of time spent on their mobile by Americans was 4 ½ hours. From another study by Asurion in 2019, they reported that Americans consult their phone on average 96 times per day [Cision]. Another study, using a small sample size (site has now been taken down, but is visible through the Way Back Machine), said that its Dscout users touched the mobile on average 2,617 times every day. Whatever way we cut it, we have gone from “don’t leave home without [your Amex]” to “don’t think about going anywhere without your smartphone.” If the West ever gets into the super apps, as in many countries in Asia, expect these numbers to soar.

Figure 2 - Statista Study on Mobile Usage in USA 2021

Silent ships passing … in the street

Whether we’re standing in a queue, sitting idly in the bus (and some underground metros with wifi), or waiting for a friend, our instinct is to pull out our phone rather than talk to someone else nearby. Walking down the street, the number of times I interact with a stranger is desperately small. I’ve observed that there are five possible interactions as we walk by one another:

1. Looking up but blandly ignoring everyone, possibly listening to some music/podcast in the earphones

2. Head down on the phone and in danger of walking into another pedestrian (or worse, stepping out in front of moving vehicle or bicyclist)

3. Sharing a furtive look at one another or possibly giving a small wave (for example, of thanks to a car that stopped for you)

4. A warmer exchange in the form of a smile, a more welcoming look in the eyes

5. God forbid, we might even say, “Good day.”

Do I have them all covered? Surely not. Of course, there’s also the lurker or pervert who seeks to engage with a stranger for nefarious reasons. But let’s get past such an individual. In a large metropolitan center, the truth is that we’ve numbed ourselves from interacting with our fellow citizens. In smaller towns and villages, you can more easily run into a friendly face. I recall how easy it was to strike up a conversation with two fellow shoppers in a small town on the banks of the Beauly Firth in North Kessock, Scotland. But these types of interactions are an exception in larger cities. I can almost remember every time I’ve had a conversation with a stranger on the bus this year. It usually starts with a shared observation of what’s happening on the bus. And then the willingness to pursue the exchange tenuously hangs on various little micro signals. When I pass by someone and our eyes meet, some will just blandly stare back, giving no sign of life. Others will smile, especially if I smile first. My wife has a smile that lights up a room. It’s a darling trait. People very often come over to speak to her in the streets or public transportation because she immediately engages with her smile and very quickly, people share something personal. It has happened in the most unexpected circumstances, with people of all types in different countries. (N.B. This doesn’t change the fact that she is not a diplomat in other situations, e.g. when it comes to giving straight talk to me or others in the family.)

A smile is worth a thousand words

When I was asked by a friend to house-sit their adorable Pomeranian, every time I walked outside with him, he inevitably provoked a smile on the faces of passing strangers. He has a truly adorable face. And it’s true that, being an animal lover, when I’m in a bus or train and a dog (on a leash) is nearby, I can’t help myself in wanting to lean over and pet it. The pet dog is a great conversation starter. But, shy a pet dog or a beaming smile, interactions with strangers are dastardly rare in most metropolitan centers.  

Why do we avoid one another so much?

There’s no doubt that part of the problem is that, from an early age, we’ve learned not to trust a stranger, especially the man in a mac bearing unsolicited gifts. From there, we grow up and are quick to impose the same thought on our own children. Better to be safe, than sorry. Very quickly this becomes: you can’t leave your children alone, any time. Better to always wear a helmet, even while riding a tricycle. No physical rough housing. Certainly, no tackle rugby. More recently, let’s wash our hands of all contact. No spreading of germs, ironically so useful for building our immunity systems. Perhaps, we can thank Kim Wilde, with her hit song, for reinforcing the idea of not trusting a stranger. It’s the precautionary principle that has been around since the 1970s and was underscored in Greg Lukianoff and Jonathan Haidt’s The Coddling of the American Mind. The mobile phone and the dopamine hit of a LIKE on your latest TikTok upload or an emojized response on your Instagram Story provide a great way to think you’re engaged with the world. Meanwhile, it’s passing by you in front of your very eyes. There’s something positively titillating of meeting someone new and it doesn’t have to be sexual or untoward. Think of how we’re wired to buy what’s NEW on the store shelf. There’s something exhilarating about the discovery. Because it’s new, it’s unknown. Eventually, it’s a surprise. Just think of the excitement of opening up a present under the Christmas tree.

I like the feel of a stranger

I wrote a song back in the late 1980s with a friend, entitled A Convinced Man (that you can hear the full track on the back end of my podcast episodes) and I still hear myself in it. It starts:

I like the feel of a stranger
Tucked around me
Precipitating the danger
To feel free
Trust is the reason
Still I won't toe the line.

Among the more worrying issues in our society is a general sense of disconnection, a lack of practice at interaction and a certain malaise. As much as we’d like to point to tech as being THE problem, we’ve been talking about depression, narcissism and a loneliness crisis for many years, pre-dating social media. Christopher Lasch published The Culture of Narcissism in 1979. Martin Seligman and others have been clamoring about the increase in depression rates in the US in the second half of the 20th century. As reported in this 2009 article in Utine, “[a] nine-nation study by epidemiologist Myrna Weissman of Columbia University and a cross-cultural group of international scholars found that people born after 1945 are three times more likely to experience depression than people born before.” In 1998, The School of Life was bemoaning the end of family meals and the crisis of loneliness. For sure, technology and social media in particular may have given us more ways to connect, but they’ve exacerbated our inability to be connected.

Connecting with strangers

For many years, I have made it my intention to try to meet someone new every day, even if it’s just a short exchange at the grocers. To mark my intention, I will color my ‘new person’ meeting in green in my calendar. In fact, I color code other important events with a variety of colors, including my sports outings (rose), when I’m being interviewed (red), my podcast rendezvous (brown) and travel (bright yellow). Even during the pandemic lockdown, beyond meeting Doris and a few others IRL, I used an application called LunchClub to set up meetings with new people (via Zoom). These have led to many real-life encounters and friendships. Another online meeting app that still exists is Connect.Club, but most of these Covid pop-ups have now closed down. The key here is having the intentionality to go out of your way to meet strangers. [N.B. Another fine idea is Out of the Blue that rifles through your personal digital address book to prompt you to rekindle an existing contact.]

Figure 3 - Color-coded agenda to visualize what's important

The method to the madness

I’ve long been an admirer of Stephen Covey who coined the term of the abundance mindset in his bestseller, 7 Habits of Highly Effective People. This mindset suggests that there is more to life, more potential, more options, and more to go around. It’s a useful attitude to cultivate in general, and it is especially practical when it comes to meeting new people or networking. It helps you move from a what’s in it for me attitude (i.e., transactional) to a what’s in it for us. There are three key points to highlight in our effort to meet and engage with strangers. The first is that you have to have a genuine desire to meet. This means coming without a critical or judgmental mindset, regardless of first appearances. If you don’t have this attitude, despite your best efforts, that negative sentiment will filter through. While I’m often a little impatient with small talk, it’s obviously an important first step. It’s a way of plugging into one another and evaluating to what extent each is willing to engage. Of course, small talk boundaries and habits depend on your context and culture. In this, I’m more like the Swedes who view small talk as futile. In Sweden, it “is referred to as kallprat (‘cold talk’) or dödprat (‘dead talk’).” [Source: BBC] The article goes on to write, “For Swedes, the purpose of talking is to exchange meaningful information, and engaging in purposeless chit-chat simply isn’t valued.” In my experience, in other cultures, it’s almost impossible to get beyond small talk with a stranger (e.g. Japan). It’s as if moving to meaningful or deeper topics are reserved only for bona fide friends. But as my pal and fellow author, Neal Schaffer said, you never know what someone else will find meaningful. Sometimes, just saying hello can cheer up someone’s day.

Not everyone is, or must be, a friend

In the same vein, it’s always intriguing to see how people from different cultures view concepts of friendship. Some thrive on having hundreds of “friends” while others firmly stick to only calling a handful of people as real friends. The rest are just acquaintances. Yet, some of the conversations that I’ve had with strangers have been thrillingly real and astonishingly deep, exploring topics in ways that are so different from the standard. When engaging with a stranger, the idea is not to have a goal. It’s just a wee journey. What I’m hoping to do is connect. Nothing more. Nothing less. And then we see where it leads. Key to this is just letting the process happen. That said, if I find an opening and time is apparently available (two big ifs), then I will be eager to dig in for a deeper exchange.

Two ears, please

The second concept is to be willing to listen much more than you wish to speak. Putatively attributed to the Greek Stoic philosopher, Epictetus, he is reputed to have said that we have two ears and one mouth for good reason.

“We have two ears and one mouth
so that we can listen twice as much as we speak.”
-Epictetus

In one of the biggest afflictions of our day, people are struggling to feel heard. Everyone, at the same time, seems to be too keen to speak. Our attention spans are reduced, our impatience is noticeable, and our listening is poor. I attribute this in part to the surfeit of information, where everyone feels that they have too much going on and too many inputs. They know too much? The second reason is the fact that most kids grow up in a household with only one or two siblings, if any at all. Gone are the days where couples spawn football teams, where kids learn to live in community at home, and don’t ‘own’ the airwaves. Compare that to today’s more entitled kid. The stark truth is that this heightened sense of individualism – and its uglier cousin narcissism – has been around ever since the 1960s and was exacerbated through the 1980s. Not to throw out the baby with the bath water, but we’ve gone ballistic in our desire to stand out as individuals. In a recent podcast, I was listening to a woman who was extolling the fact that people now want to have hyper-individualised tombstones. It’s not enough to mark a name and date of death plus perhaps a spiritual thought. Today, you can now find tombstones with the deceased’s favorite recipes (usually sweet apparently). In a BBC World Podcast interview, Rosie Grant, spoke that with today’s tombstones, “the sky’s the limit.” Referring back to my Model of Infinity, this practice falls nicely into our obsessive need for hyper personalization and tending toward immortality. We need to get back to reality. We need to dial into our cosmic insignificance, our imperfections and our mortality to help us focus on what’s important, on having a stronger moral compass, on community and on our civic responsibility.

Please elaborate!

Having come into contact with a stranger with the intention to engage, working through the small talk, giving the exchange the necessary time to develop and applying strong listening skills, the third key point is to ask good questions. This is, at some level, a natural extension to good listening. The notion of a good question is that it keeps the focus on the other person. By asking an open question that follows on from you’ve heard, you are asking them to elaborate on THEIR story. As Rob Volpe, who’s been a guest on my show, wrote in his book, he likes the expression: please, tell me more about that.

Tell me more about that
-Rob Volpe

This is a particularly good question when what you’ve heard might rub you the wrong way. First off, you might have misheard or misunderstood. Secondly, even if the point of view is different or irritating you, find out how and why they have developed this perspective. If you plunge into the background, it will help you understand them. And, by showing a genuine interest (rather than preparing to jump all over them), you’ll start to build bridges.

So, there’s a three-step process to ‘meet’ a stranger in a more meaningful manner:

1. Be intentional and genuine in your interest to connect. Avoid having expectations or being transactional. Make sure you make the time. You’ll also need to gauge their availability, too.

2. Listen more than talk. Plug into what they’re saying without judgment and avoid (or at least think twice before) bringing it back to you.

3. Ask good open questions that follow the thread of what the other person is saying. Make them feel heard. Your time will come. And in due time, look for ways to delve into deeper areas.

Practice makes… well, still imperfect

Going out and engaging with perfect strangers in the street is not easy. Usually you need some excuse, like a cute dog or an odd event that you both observe. In restaurants, for example, there are more obvious ways to connect, like noticing the other person’s food. There are codes and implicit protocols in certain locations (think: private clubs). For sure, the more you do it, though, the easier you will find it. The awkwardness will subside. You’ll start recognizing patterns. Your knowledge, general culture and world experience will help, especially with people from totally different cultures. But the key is to focus on the other person. Observe their little facial expressions, listen to the timbre of their voice. Listen and ask open, ever more probing, questions with tact.

A meaningful conversation is an exchange

Back to Doris. I can say that my encounter with Doris was not just good for her. It was uplifting and important for me. She used to say to my wife that I was hot(!) and that she preferred to be left alone with me. My wife applauded and went along with it. Sure, I felt like I was doing a good service. But more significantly, I was benefitting as Doris offered out her observations, experience and wisdom. It was a genuine exchange. She had a way of looking at the world that was so refreshing, so memorable. She would joke with me on my rounds, “Oh darn, I woke up alive again.” She had suffered a horrendous car accident (hit as a pedestrian when she was 84 years old) which left her heavily scarred all the way up her legs. She never complained, although her hearing aid bugged her at times. When Doris finally passed, quietly in her sleep, my wife and I attended the small memorial service. We were all diligently distanced from one another, an act that surely Doris would have disdained. With a memory of her daintily painted lips and her sparkling eyes, she still brings a smile to my mind.

I leave you with a quote from one of my all-time favorite songs by my all-time favorite band:

Wind in the willow's playin' "Tea For Two"
The sky was yellow, and the sun was blue
Strangers stoppin' strangers just to shake their hand
Everybody's playing in the heart of gold band, heart of gold band.
From Scarlet Begonias – Lyrics by Robert Hunter

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If we don’t practice speaking with those we don’t know, we’ll lose our ability to meet and, more saliently, lose a chance to learn and expand our horizons. My desire is to encourage you to go seek out a stranger and start a conversation. Let’s re-engage with one another without the security of knowing what everyone thinks and feels. The more you do it, the easier it becomes.