5 Ways to Start Conversations with Confidence

If you’re experiencing anxiety at the very idea of talking to a stranger—or an acquaintance or colleague that you haven’t seen in awhile—this guide is for you. 

There are many reasons why starting a conversation with someone outside of your inner circle may seem intimidating, unnecessary, or even a bit annoying, depending on your mood. Maybe you’re shy, don’t know what to say, or are afraid of potential rejection. Maybe you prefer solitude. Maybe you feel more comfortable observing and listening than participating. Maybe you feel that you don’t have anything to add. But small talk of all kinds is an unavoidable part of life. And, when done well, it can be a sweet, touching, and thrilling experience. It’s a bridge between your life and the lives of others. 

Small talk can be a moment to establish instant commonality and quench curiosity. It can also be the first step to building a deep, meaningful connection to another. It can be a quick conversation with a stranger in line, talking to your cab driver, catching up with a co-worker on a Monday morning, or even spotting a lovely person across the room and approaching them for the very first time. Talking to somebody who you initially judged on looks alone can also instantly flip your biases and expand your perspective. No matter the situation, learning how to start conversations with confidence improves your overall well-being.

Building Confidence Requires Practice

Feeling confident around other people starts with feeling confident in yourself—and it takes practice. YouTube has countless videos of confidence-building affirmations that you can listen to with your eyes closed whenever you’d like. Search for ones that are spoken in a soothing tone. Focus on your breath as you listen and repeat each affirmation. Doing this before you head out of the house can have a profound effect on how you feel in the world. 

Confidence is a mindset. For some, that mindset is ever-present; for others, it takes some work to get there. If listening to affirmations isn’t your thing or if you’d like to try another practice, play with the following questions: 

• What are some things you like about yourself? 
• What are you good at? 
• What would you like to be better at?
• What are some challenges you have overcome for which you are proud of yourself?
• What’s a new challenge you’d like to take on?
  

These questions are meant to be answered on your own, though feel free to ask a close friend or family member how they would answer these questions about you. Sometimes it helps to get an outside perspective, especially if we’re struggling with self-esteem. The people who love us are often much kinder to us than we are to ourselves.

Start with what’s right in front of you.

Every situation has a context. You can draw from that context because it is the thing you’re sharing with the other person at that very moment.

• If you’re in a museum, discuss the artwork around you. 
• If you’re at the market, ask if they know how to pick the perfect apple. 
• If you’re in a club, talk about the music. 
• If you’re in a café, ask if they have a favorite item on the menu.
  

Don’t judge the topic you choose too harshly. We all know that talking about the weather is often considered tedious, but if you and another person are caught together in the rain, the rain is the context that brought you together. If you’re sitting next to someone on a park bench on a beautiful day, you can be confident that you both enjoy going to the park and sitting in the sunshine. From there, you can ask if this is their favorite way to spend a beautiful day; if they brought a good book with them; or if they can recommend a great restaurant near the park. If they want to engage, they will. If they don’t, they won’t. If they seem to be engaging only to be polite, pick up on the social cue and leave them be. It’s not personal. They may be an introvert or prefer solitude. These situations are great practice because, in most cases, you’ll never see this person again.

If you’re shy, nervous, or out of practice—it’s okay to say so.

Do not think that you’re the only person who doesn’t know how to approach people or that everybody else always knows the right thing to say. Flowing conversation doesn’t come naturally for many people, especially now. We live in a time when many of us often resort to  looking at our phones rather than talking with the people around us. This dynamic not great for our socializing muscles, but engaging in small talk is the best way to exercise that muscle. You can even say to someone else “I can’t believe how much time I just spent looking at my phone. I guess sometimes it feels easier than talking to other people. Do you ever feel that way?” 

Remember that you are a mystery to others just as they are a mystery to you. When you’re feeling introverted, it may seem like the whole world can see you blush. But most people have a degree of shyness, and by acknowledging your own nerves, you may be putting them at ease, too. 

Look for commonalities.

The best questions for starting a conversation with confidence are the simplest. Focus on questions that help you find something in common with the other person, whether it’s a significant place, activity, or interest. 

Some of the best small talk can come from finding out that you grew up in the same area as another person, that you know the same diner or ice cream shop, that your school played each other in sports, that you share some sort of similar culture. 

The opposite is true, too—two immigrants from vastly different countries may bond over the fact that they're both in line at a bodega in the new city they now both call home. 

You don’t have to look too hard for things in common. A simple and polite “where are you from?” or “have you hiked this trail before?” can go a long way. 

Embrace differences.

If questions such as “where are you from?” or “have you hiked this trail before?” yield surprising results that you have nothing in common with, embrace it. “Wow, I’ve never heard of that area” or “I’ve always wondered what it’s like to grow up there; did you enjoy it?” or “Oh, your friend dragged you on this hike? What activities do you prefer?” 

And if you find yourself in an uncomfortable conversation, ask yourself: 

• Do I want to excuse myself from this conversation? 
• Or do I want to use this as an opportunity to challenge myself to learn how this person came to think or behave this way?
  

There’s no pressure either way. That’s the beauty of small talk. Once you have the tools to start conversations with confidence, you’ll soon learn how to end conversations with confidence, too.