An Introvert’s Guide to Speaking to Strangers

8 Ways to get past the awkwardness

Illustration by Cynthia Marinakos.

Growing up, I much preferred exploring the depths of Middle Earth under my warm, secure doona covers than speaking to people I knew. Add to that I was shy and an introvert. It was embarrassing to feel my face heat up, beet red when people turned their attention to me. There was no way I’d willingly go up to a stranger and start a conversation. That’d be too damn awkward.

And it’s not just me as a child. I’ve noticed at events and waiting rooms, parks, and stores: many adults don’t feel comfortable speaking to strangers. We’d rather ignore each other. Mind our own business. Even when inside we’re dying to ask a question, make a comment, or help.

What holds you back from speaking to strangers?

You’re an introvert too. Also, perhaps it doesn’t seem socially acceptable. You don’t feel safe. You don’t like talking to people you don’t know. I mean, why do you need to torture yourself making small talk with strangers when you‘ve got a phone full of numbers.

Well over the years, I’ve realized the value in speaking to strangers. I forced myself to practice repeatedly, especially when I lived overseas a couple of times on my own.

I made a goal to speak to one stranger a day for a week. I said good morning to random people in their gardens while ran by. I spoke to others waiting to be interviewed. I made small talk with people at office functions. Chat to bus drivers as they drove. Laughed with security guards at clubs.

It was so damn hard at first. Daunting and uncomfortable. I felt “What if they ignore me?”. My stomach was in knots sometimes. And my heart pounded loudly. I sometimes rehearsed lines in my head — that I didn’t say. I didn’t want to feel rejected. Stupid. Embarrassed. Like a loser. It seemed like too big a risk to take.

Yet I pushed through the awkwardness and feeling shit scared. And I’ve discovered that daring to approach strangers online and offline is worth it. It can lead to valuable business referrals. Insightful business mentors and accountability partners. It can lead to careers you never imagined existed.

Stepping outside your comfort zone can lead to precious lifelong friendships. Or short term yet meaningful friendships. It can lead you to free passes. Free food. Invites to VIP lounges at the airport. Lifts home. People lending you their phones when you’ve lost yours. Taking you to places you’d never see as a tourist. Sharing stories you’d never imagine.

Still, it’s not easy to do. Good thing is, talking to strangers is a learned skill you can easily master with practice. There are plenty of opportunities to improve. And today I want to share with you 8 powerful ways I often use to connect with strangers:

1. Find common ground

It’s been found the less we know about a person, the more we like them when we find actual similarities. It’s also easier to carry on a conversation when you find something in common:

A person.
A dish.
The town you grew up.
Where your parents came from.
The industry you work in (or worked in).
A travel destination.
A hobby.

The possibilities are endless. For instance:

“Hey I lived in Vancouver for a year. What part of Van did you live in?”
“I’ve worked out at that gym for the past 5 years too. Have you tried any of their classes?”
“I play the piano too. What are your favorite tunes?”

Key takeaway 1: Find common ground.

2. Give compliments

People don’t get as much positive reinforcement as they’d like. We all like to feel appreciated. We all want to be seen. Mark Twain once said “I can live for two months on a good compliment” and a 2008 study shares the science behind this feeling: receiving a compliment has the same positive effect on people’s brains as receiving a financial reward.

To make sure it sounds genuine, be specific when giving compliments. For instance:

“Gosh I love the dress you’re wearing. That color looks amazing on you and it has a gorgeous cut. Where did you get it from?” (Be careful about your compliment sounding like a pick-up line).

“Great speech. It was fascinating what you said about how every big company needs a startup department. And the example you gave was spot on.”

“Thank you for giving us such great service. You were so quick and we hardly noticed you here but got everything we needed when we needed it.”

Compliments help you as the giver, too. When you make the effort to pick out the good in others, it can help you find gratitude and appreciate people and moments you might usually miss.

Key takeaway 2: Give a compliment.

Key takeaway 3: Make eye contact

Eye contact is a simple yet powerful way to acknowledge a person. Eric Wesselmann, a social psychologist at Purdue University in Indiana ran a social experiment involving 239 pedestrians. He found the people who weren’t acknowledged by passersby with eye contact immediately felt socially disconnected. They felt pain at being overlooked.

This is consistent with eye gaze research by Wirth and others that found eye contact helps a person feel they’re included — and ostracized when they don’t get it.

Key takeaway 3: Make eye contact.

4. Smile

Smiling is infectious. It’s hard for someone not to respond to you when you’re smiling at them. Researchers ran a smile-based experiment across 7 countries in 2014. They found people with smiles across are perceived more positively compared to people who don’t smile. It tells them you’re approachable, open, and friendly.

Many other people have trouble speaking to new people too. A smile breaks barriers. A bonus is it’s been shown to reduce stress and helps us feel happier and live longer.

Of course, a genuine smile is preferable to a fake smile. How do you make your smile genuine if it doesn’t come naturally? In an interview with Brain World Magazine in 2019, Neuroscientist Andrew Newberg, M.D.and therapist Mark Robert Waldman share how they train people to build trust through smiling:

“We just ask a person, before they engage in a conversation with someone else, visualize someone they deeply love, or recall an event that brought them deep satisfaction and joy.”

Key takeaway 4: Smile.

5. Anticipate the stories people hold within

Walt Disney once said “A good story can take you on a fantastic journey”. Well, people are walking books, filled with good stories: their childhood dramas, their interests, the people in their lives, the insights they’ve gained, the screw-ups, countries visited, former lifestyles.

Our pasts may seem boring to us who have lived with ourselves our whole lives — yet to others, your stories are as intriguing as a New York Times best-selling book or a box office hit movie. You have the opportunity to access incredible details when you approach strangers with the same interest, excitement, and anticipation you’d feel before watching a hit movie or reading that popular book.

I’ve come across people with intriguing stories. For instance, the Greyhound bus driver taking me from LA to Vegas shared how he worked in prisons — then changed careers after he was held up at gunpoint. While on a morning run in Vancouver, I stopped by for a chat with a guy in his front garden. We continued the chat over blueberries and milk in his back garden, where he told me about his life as an American Airlines pilot.

Imagine the next stranger you see holds the most fascinating stories you’ll ever hear: about people, places, and adventure. Extraordinary real stories. When you’re genuinely interested in people, it makes it easier to speak to them. If you’re not interested in people, fake it to start with. You may find yourself enjoying it after a while.

Key takeaway 5: Anticipate great stories from people.

6. Listen actively

Listening is a tough skill. Our minds naturally wander. We start crafting a reply in our minds. We use our assumptions, expectations, and intentions to interpret what’s being said. We don’t truly tune into the person. We shut the door if they say something we don’t want to hear.

Add to all that, we’re not used to communicating face to face anymore. And we don’t pay as much attention to new information because we know can always Google it and find it when needed.

We’ve got to get better at it: actively listening to another is an underrated gift. In their Listening Circle research paper published in 2017, Researchers Kluger and Kitzchakov tell us high-quality listening frees speakers from worrying about how they’re coming across to others — this helps them feel psychologically safe and reduces their social anxiety.

Yet it’s a tough skill to learn. In The Handbook of Listening, authors Worthington and Bodie shared a finding many organizations don’t bother to focus on: listening may improve an employee’s satisfaction in their job more than page. More money and thought are invested on pay than teaching managers how to listen.

A humbling benefit of being an active listener is people open up: Friends. Family. Colleagues. Strangers. They invite you into their lives. They tell you things they’ve never told anyone. Or rarely share. The benefits of discovering new insights and truly understanding another with empathy are worthwhile.

A few tips on active listening:

  • Focus on your speaker’s left eye, notice their eye color
  • Avoid interrupting: listen for at least 17 seconds before saying a word
  • Avoid thinking of a response
  • Ask questions to clarify what they’re saying and dig deeper: ask ‘why’ 5 times

“We have but two ears and one mouth so that we may listen twice as much as we speak.” — Thomas Edison

Key takeaway 6: Practice active listening.

7. Ask questions

Asking questions is a great way to draw people out. It can be easier to answer a question than it is to ask one. This can be tough, especially when we’re shy. We often feel too awkward and self-conscious to utter a word. We’re much more comfortable in our own heads.

Having a list of helpful conversation starters takes the pressure off approaching strangers. I’ve found these casual conversation starters work really well, especially when combined with the other tips in this piece, such as a smile and having a genuine interest in people:

“Hey how are you going?”
“It’s pretty hot/cold today isn’t it?”
“I’m Sarah. What’s your name?”

At a shop:

“Has it been busy today?” followed by “When do you finish?” (But don’t say it in a creepy way like you’re a stalker)
“How was your day?”

At a function:

“Hi I’m Joe. What’s your name?”
“Oh I love the onion relish on these sausage rolls. What’s your favorite dish been so far?”
“What do you do for work?”
“How do you know <person>?
“I got a bit lost looking for this place. Have you been here before?”
“What do you reckon about <a speech or other thing related to the function>?

At a cafe:

“I’m tossing up between the risotto or the marinara: which do you recommend?”
“What’s your favorite dish here?”
“That looks delicious. What it is?”

You might feel shy or intrusive asking questions. Yet research has shown asking questions makes you more likable. Particularly when you follow up. It shows you’re responsive, you’re listening, you help the other person feel validated. And you care.

Key takeaway 7: Ask questions.

8. Feed your mind positive talk

When you’re alone with your thoughts attacking you constantly, it’s easy to feel doubtful and negative. It’s easier to walk past strangers, ignore them, and avoid their eyes when you feel uncomfortable and your negative thoughts keep you there. Positive affirmations can help you break past your discomfort and build your sense of self-worth and confidence.

Instead of focusing on:

What if they ignore me if I speak to them?
I don’t know them, why should I say anything?
They’ll wonder why the hell I’m talking to them
I feel stupid talking to a stranger

Tell yourself:

I’m a kind, beautiful person
I am enough and always have been
If I want something to happen in my life, I have the power to make it happen

Make positive talk a habit and over time, your mind’s negative talk won’t hold you back.

Key takeaway 8: Focus on positive talk.

Will all this work all the time?

No. Not everyone will respond in a positive way to your acknowledgment or interaction. Other people may feel uncomfortable with strangers also. The neighborhood, culture, personal experiences, and other factors might make it feel strange or dangerous for people to respond.

Be aware of these for yourself — and for others. Find safe, appropriate opportunities to connect often. As you keep practicing, you’ll get savvier with people and your environment. And you may soon enjoy speaking to strangers as much as I do.

Just remember this when you feel awkward and unsure about whether to approach a stranger: We all want to be included. It’s an evolutionary response where survival comes from being part of a pack rather than alone. We might like to put up a front to appear as if we don’t mind being alone. But deep down, we need each other.

In a nutshell

It’s natural to feel awkward speaking to strangers. Yet when you acknowledge someone even with a simple nod, you make an impact. You fulfill a need we all have: to feel included and connected socially. This can help you feel more joy each day as you discover wonderful people in your daily life, your career, your business, and your relationships.

Ways to break down the awkwardness of speaking to strangers include:

  1. Find common ground
  2. Give compliments
  3. Make eye contact
  4. Smile
  5. Anticipate the stories people hold within
  6. Listen actively
  7. Ask questions
  8. Feed your mind positive talk

Like anything, the more you practice, the better you’ll get speaking to strangers. And the less awkward it will feel. Give it a go for a week and see what happens.

Aussie Copywriter. I love rock climbing high ceilings and hiking amongst ferns >> 10 Proven ways to attract more Medium readers:

Get the Medium app

A button that says 'Download on the App Store', and if clicked it will lead you to the iOS App store
A button that says 'Get it on, Google Play', and if clicked it will lead you to the Google Play store