How to Make Small Talk with Strangers: My 21

One of the hardest skills to master is figuring out how to make small talk with strangers. People always avoid this topic and are reluctant even after years of practice, but it’s important for survival! Get tips from an expert on what makes a great conversation starter from some simple questions in your everyday life.

“How to Make Small Talk with Strangers: My 21 Years” is a personal story of the author’s experiences in making small talk. The author talks about how he has learned to make small talk, and how it can be done. Read more in detail here: how to make small talk with a woman.

Vintage people at grocery store checking out small talk with cashier.

One of the most surprising things I noticed as a parent is how much more you wind up chatting to strangers. This is partly due to the fact that people are more inclined to approach you when you have a child with you, and partly due to the fact that children are excellent icebreakers.

Mason, my 3-year-old son, has no qualms about approaching people and striking up a conversation. If we didn’t intervene, he’d probably go away with another family.

In fact, current social science study shows that having a toddler to break the ice with more strangers might make us all happier. Nicholas Epley and Juliana Schroeder, two Chicago behavioral scientists, discovered that persons who chat to strangers are happier than those who remain to themselves.

The researchers addressed travelers at a railway station in the Chicago region and invited them to breach the “rules” of public communication. A group of passengers was urged to engage in conversation with the stranger who sat next to them on the train that morning. A second group was advised to remain to themselves and observe conventional commuting conventions. A third group was not given any instructions at all.

The researchers asked the passengers a simple question at the conclusion of the train ride: were they happier or less pleased when they had to talk to their seatmates?

Surprisingly, the commuters who spoke with a stranger reported higher levels of happiness than the other groups.

The intriguing finding is how reality differed so much from the commuters’ own forecasts. When Epley and Schroeder asked commuters to anticipate how they would feel after speaking with a stranger, they said they would feel better if they kept quiet. The exact opposite turned out to be true.

“Inferences about what others think, believe, feel, and desire influence our everyday activities,” says Epley in Mindwise: What We Think, Believe, Feel, and Want When It Comes to Others. The difficulty is that our conclusions are often incorrect. And it turns out that if we simply spoke to each other, we’d all be happy. What is the explanation behind this? When we chat to strangers, we want to project a positive, welcoming image of ourselves. As we’ve seen previously in the Art of Manliness, the way you behave affects how you feel – by doing, you become! To put it another way, if you’re in a bad mood and turn up the heat while chatting to a stranger, you’ll start to feel a lot better. Interacting with strangers might help you feel better. 

AoM has previously written on why it’s important to strike up a conversation with strangers, as well as a thorough guide on how to do so. I took this advise to heart, and in this piece, I wanted to put it to the test. I decided to see whether conversing with strangers makes you happy.

Over the period of 21 days, I made an attempt to strike up conversations with strangers wherever possible.


My 21-Day Conversation Experiment with Strangers

Vintage men on skis talking smiling small talk.

My experiment’s parameters were simple: for 21 days, I would seek out chances to strike up conversations with strangers in public areas. I didn’t go about accosting every stranger I saw in public parks and Greyhound bus stops, but I made the decision to attempt to create the environment for more contacts with new individuals. When given the choice of sitting alone in a public area or in shared seating, I would choose shared seating and seek out chances to converse with my seatmate.

I won’t bore you with a lengthy account of every encounter throughout the course of the 21 days, but I will offer a few instances of normal interactions from my time as a human guinea pig, along with my commentary/reflection on each one.

I also give a few takeaways from my 21-day experiment that you may utilize to improve your ability to converse with strangers.

Calabasas, CA, Friday, May 9th, a hotel pool. As I prepare to go swimming with my kid while visiting my family’s hometown for a wedding, I come across a guy sitting on the side of the hotel pool. He has a tiny white puppy, which my kid strokes, and we begin to converse. It turns out he and his family had just relocated to the region from Chicago. I tell him all I know about the area, the schools, and the specific communities where he wants to purchase a house.

He appreciates my counsel about the local high school, which is the same one where I graduated.

I felt helpful and valued as a result of the connection. His daughter is going to start high school at my former school, and he appears comforted when I tell him how fantastic it was.

A rest station on I-5 between Los Angeles and San Francisco on Monday, May 12th. We stop for lunch at a rest area on the I-5 highway on our journey back to the San Francisco Bay Area from Los Angeles. “Coastal Maine Botanical Garden” is written on a man’s t-shirt. I’m thinking about responding since we have relatives in Maine and have spent summers there. However, I remain silent.

How I Felt: I afterwards regretted not speaking out. I adore Maine and am interested whether the Coastal Maine Botanical Garden is located near where we have spent our summer vacations. Sure, I could look it up on the internet, but I would have preferred to speak with the guy about the region.

My home, Tuesday, May 20th. Three workers from a tree trimming service are coming to our home to trim our trees. Normally, I would leave them to work outdoors without interacting with them. In this situation, my son Mason is eager to see the guys at work, so we open a side door to allow us to observe them more closely. We watch as three guys ascend the trees with the dexterity of monkeys and reach the summit.


I half-jokingly inquire of one of the tree trimmers about how often they fall out of trees. “Almost never,” he adds, which is incredible. “I’ve been climbing trees for 27 years,” one of the tree trimmers adds, adding that he once fell out of a tree and injured his knee.

What I Thought: I really enjoyed this chat. It’s not every day that I get to speak with someone whose job it is to climb trees, and it was fascinating to hear how they do it. I also feel like I’ve gained fresh knowledge.

On the boat, Thursday, May 29th. I usually drive to work, but today I have a meeting in San Francisco and must ride the boat from my house in Marin County. I decide to take advantage of this chance to practice small chat in the most challenging of circumstances: on a daily commute with other commuters.

During each leg of the journey, I purposefully sit at public tables in the hopes of striking up a conversation. Despite exchanging a few niceties, I did not engage in any significant dialogue.

I had a conversation with a lady about the quantity of spray kicked up by the ship at one point. The talk eventually ends, and she returns to her book, while I go out to get a cup of coffee.

How I Felt: To be honest, I’m sad that I didn’t participate in more discussion on the ship. I’m not sure why it seemed to be so challenging. Perhaps I could have tried harder, but I know that digital gadgets often obstruct my efforts. The most essential takeaway from this experience is that you must move swiftly by starting up a discussion with individuals as soon as they sit down, before they put on headphones or begin reading a book.

Main Street, my hometown, on Friday, May 30th. On Friday night, my wife and I will attend an outdoor block party with our 3-month-old son. The infant is a terrific discussion starter, particularly because he’s wearing huge noise-cancelling headphones, which, to be honest, look ludicrous on a newborn.

When you have a kid with you, it’s almost too simple to start chatting to people because strangers will approach you and interact with you. When I’m out and about with the infant, on the other hand, I like the chance to meet new people.

The Lessons I Learned From My 21-Day Experiment

Vintage African American black barbershop men getting haircut.

In general, I was pleased with the majority of my contacts with strangers. Almost every encounter made me feel a bit better. I also felt like I learnt new things through conversing with folks from other walks of life that I would not ordinarily interact with.

I didn’t have a single occasion when I felt uncomfortable or as though I was bothering someone by conversing.

I will, however, mention a few disappointments:

  • It’s not always simple to strike up a conversation, even for an extrovert like myself. I consider myself to be an outgoing person. Despite this, there were occasions when I hesitated or lost opportunities to engage in conversation because I didn’t know what to say. This may come as terrible news to introverts who already struggle to strike up a conversation with strangers, but the fact is that it’s not simple.
  • Phones and digital gadgets are significant impediments. I believe that the most significant obstacle to engaging with strangers is the use of digital gadgets. I tried to strike up a conversation on occasion, but when I glanced around, practically everyone was engrossed in their phone or other digital gadget. It seemed to me that speaking out would have been an interruption.
  • I did not form any long-term relationships. I’d want to say that as a consequence of my 21-day experiment, I made new lifelong friends, met new neighbors, scheduled playdates for my kid, and secured new customers. Regrettably, this was not the case. Making casual conversation with strangers isn’t tough for me, but converting those casual interactions into a long-term connection is.

The good news is that there is yet hope. I came away with four easy and precise ideas based on my trials, which you may follow if you’ve been persuaded that you should make more of an effort to engage in conversation with strangers.


4 Ways to Boost Your Happiness by Making Small Talk with Strangers

Vintage men in suits riding subway talking laughing.

1. Put your iPhone and other electronic devices on the table.

As I previously said, phones, tablets, and e-readers posed a significant barrier to discussion. So the greatest thing you can do is put down your own digital gadget to ensure that you are not interfering with others’ conversations.

Of course, I’m just as guilty as the next person for pulling out my phone if I have to wait in line at a shop or meet a friend. But I’m starting to wonder whether being constantly linked to our digital gadgets means we’re all missing out on those serendipitous meetings and discussions that might make life a bit more fascinating. It’s a compelling case, at the very least, for taking a tech Sabbath once and again.

For example, my wife’s parents met while waiting in line to apply for a job. They are both introverts, and I’m not sure whether they would have met if smartphones had been available at the time.

2. Put on a Conversation Initiator

Wearing a piece of jewelry, a pin, or an item of clothing that inspires discussion is a terrific way to start a conversation practically anyplace. A especially gorgeous tie, a huge necklace, or an attention-getting bracelet or watch are examples of this.

My father used to wear colorful ties created by Jerry Garcia that included replicas of renowned artworks when I was a kid. While I assumed at the time that these ties were purely designed to humiliate me, others would invariably remark on his ties, and he’d quickly find himself in the middle of a discussion with them. I’ve realized how valuable they are now.

Madeleine Albright, the former Secretary of State, was known for putting brooches on her lapel as a method to break the ice. This was especially crucial for Albright, who had to deal with male peers in a highly macho milieu of international diplomacy as the first female Secretary of State.

Albright describes the brooches as “an icebreaker, an opening.” “A little bit of levity goes a long way.”

Following my experiment, I see the value of wearing an icebreaker (or bringing a baby!) to assist initiate talks.

3. Make a complimentary remark

Making a compliment is one of the simplest ways to start a conversation. You may congratulate someone on what they’re wearing, a piece of jewelry they’re wearing, or their purse or briefcase.

After you’ve done that, you may go on to a more in-depth discussion. As discussed in AoM’s “How to Make Small Talk,” Dr. Carol Fleming’s “Anchor, Reveal, Encourage” structure is a fantastic approach to transform a light pleasantry into a deeper discussion.

During the 21-day experiment, I started a number of discussions with strangers by complimenting them on their dog or an item of clothing, and in each instance, it was a wonderful way to start a casual chat without making me feel weird.

4. Take Advantage of Conversation Opportunities Immediately

One last thing I learnt is that if you perceive an opening to start a discussion, you should take advantage of it right away. If you don’t, you may not have another chance.


During my ferry trips, I noted that there was a brief window of opportunity to strike up a discussion with other passengers as they settled into their seats, before pulling out an e-reader or putting on headphones to listen to music. You must act quickly to take advantage of these possibilities, since they will be gone before you realize it.

Go out and talk to people you don’t know.

The final piece of advise I’ll provide is to simply get out and chat to people you don’t know. What could possibly go wrong? If you attempt to strike up a conversation with someone and they are uninterested, you will very certainly never see them again.

The more probable outcome is that you’ll not only make your own day better, but you’ll also make the person you’re speaking with happy. According to Elizabeth Dunn and Michael Dunn of The New York Times, Epley and Schroeder’s study indicated that “when one individual took the effort to talk to another in a waiting area, both participants reported having a more favorable experience.”

That’s a waiting area I’d be happy to spend some time in.

Listen to our podcast on why it’s important to speak to strangers: 


Listen to our podcast on why it’s important to speak to strangers:

Former Clinton White House Writer John Corcoran is an attorney. He likes employing his young son in behavioral science research activities while he is not working. He offers a free 52-page book called How to Increase Your Income in 14 Days by Building Relationships with Influencers, Even if You Hate Networking, which you can download.



The “how to master the art of small talk for dummies pdf” is a guide on how to make good conversation with strangers. The book is written by someone who has been in the field for over 20 years.

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