Published on
Posted under
Introvert Tips

The Shy Person’s Guide to Starting Conversations with Strangers


One day, four years ago, I met a man who kickstarted my writing career and changed the direction of my life forever.

My family and I were walking to a beach in Menorca, Spain, when I saw an American couple struggling to carry their things with their two young kids in their arms. After offering to take one of their bags, our families spent the afternoon together. Since I’d been to the island a few times before to visit my wife’s sister, later that night I sent the man the ultimate guide for how to maximize their week.

“This is amazing,” he replied. “If you don’t write, you should think about it.”

I then followed the man’s signature to learn he was the managing editor of one of the largest magazines in the world.

Growing up as a shy kid with a stutter, I was petrified to talk to new people. As an adult, the story above is just one example of why I do it anyway.

Learning about other people’s stories is the most effective way to better write your own. Plus, it makes our days a helluva lot more interesting.

When it comes to meeting new people, lifting up your head and identifying ways to lend a hand is always a great place to start. Below are 6 other tips that can help you start conversations with more confidence.

1. Start smart by collecting easy wins

“The beauty of getting better at conversations is you can practice on anyone!” “Just go up to people and say hi. It’s easy!”

Whenever someone says something like this, ignore them. It’s horrible advice. Starting a conversation before gauging someone’s interest and willingness to talk doesn’t do anyone any good.

Instead, begin by identifying the people who look open to talking with you or simply practice on people who are literally paid to talk to you.

Bartenders are an easy win. The same goes for baristas and shop assistants.

This basic tip kills a lot of pigeons with only one stone:

  • These quick interactions are low stakes and when done consistently will raise your confidence.
  • If you run into the person again, you’ll have a few places to jump off from.
  • Having conversations with the people around you makes it easier for people to want to have conversations with you.

If you’re anything like me, you pride yourself on your observation skills. Lean into this quality. Find friendly faces. Say hello to people who won’t shut you down.

2. Let people know you won’t be taking up much of their time

The goal when meeting new people isn’t to display bullet-proof confidence, but rather make the person you are speaking with feel comfortable as fast as possible.

A very simple way to accomplish this is by letting people know you won’t be taking up much of their time.

  • “I’m walking out the door to meet my wife, but I’m curious….”
  • “I’m about to leave, but the cover of your book caught my attention….”

I came across this tip a few years ago when reading “It’s Not All About Me,” by former FBI agent and behavioral expert, Robin Dreeke. It immediately relaxes people.

Let people know you’ll be brief. Position your body at an angle so they have room to move. Speak slowly so they have time to get a gauge of what you’re saying.

Put these things together and you have a solid recipe for a good first impression. Just don’t forget to smile. Having a glum look on your face rarely makes people feel comfortable.

3. Cheat by reaching out to people you already know online

Once a week, over the last three years, I’ve sent an email to someone who I think is doing something cool requesting a chance to talk. The first time I picked up the phone to do this, I was definitely nervous. Today, it’s the thing I look forward to doing the most each week.

If you’re uncomfortable talking to people on the street. Cheat by making a list of the people you already connect with online and see if they’d like to chat offline. Thanks to social media, it’s easy to find a few talking points and learn what someone’s been up to.

  • “I noticed that we had a few mutual friends. Jack Woo and I went to college together.”
  • “I loved what you wrote about how to ace interviews in a recent article. I’m curious, what’s the one thing you should never say?”

The simple lead-ins get the conversation started while letting people know you’re interested in them — which plays a starring role in other people considering you interesting.

4. Charm people with your ears

The best conversationalists rarely put on a massive show. Instead, they make you feel seen by listening to you and asking thoughtful follow-up questions:

  • “That’s interesting. Have you always wanted to be a designer?”
  • “You said you lived in NYC. I’m curious, what do you miss most about living there?”

Remember this the next time you speak with someone new. Remind yourself to drop your agenda and approach each conversation as a learning opportunity. Dig into the details to get people talking about their interests and opinions.

When it comes to meeting new people, my friend Todd Brison said it best: “As an introvert, it helps me to think of each person as not as a person, but as a living story, decades in the making. My only job is to extract the story.”

5. Prioritize your notebook over your phone

“Carry a notebook everywhere you go. You’ll not only look more interesting. But you can keep track of everything you learn throughout the day.” This piece of advice from my first manager made my life so much easier.

Strong listening and observation skills aren’t nice to have characteristics when building relationships, they are the characteristics. Lean into these strengths. Take note of your own successes in conversations and those of the people around you. Keep track of the phrases that light people up.

Just don’t forget to also take note of the behaviors and phrases that bring people down. Not doing or saying the wrong thing when meeting someone new doesn’t automatically make you likable. But it sure helps.

6. End conversations on a high

“When teaching kids, no matter how boring the class is, make a point to have fun in the last few minutes. They’ll leave the class with a massive smile on their faces which in turn will put a smile on their parent’s faces.”

A friend gave me this tip years ago when I started teaching kids and I quickly discovered it works well with adults too. Everyone gets jumbled from time to time in their conversations. But most people rarely write someone off if they end their time together on a high.

Try wrapping-up your conversations when the energy is flowing rather than waiting for it to die down. It increases the odds of the person wanting to further connect with you.

  • “As I said earlier, I have to pick up my kids. I hope we get a chance to finish this conversation as what you said about X was really interesting.”

Not only does this take care of any awkward good-byes, if you pay attention to their body language and how they respond, you’ll also get a gauge of how much of a connection you’ve made.

As a shy kid with a severe speech impediment, I never would have guessed that some of the biggest moments of my life would come from gaining the confidence to talk to strangers.

Not only did it play a role in helping me discover my love of writing and now as a communication coach. More importantly, getting to know the people around me led me to meeting my wife when I first moved to Barcelona a decade ago.

Not every conversation will go well.
You won’t hit it off with everyone.

But I’ll be damned if that initial spark when two people connect doesn’t make it all worth it.

One chance encounter.
One introduction.
One conversation.

Much like picking up a new book, you never know where someone’s story is going to take you.