The Art Of Chit-Chat: 5 Simple Habits Of Naturally Great Conversationalists

How to turn small talk into real connection.

Last updated on Nov 20, 2025

Smiling woman talking on the phone and gesturing with her hands, capturing the natural energy of great conversationalists. annastills | Canva
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Before letting another person you are interested in walk away without a word of introduction and before getting left standing alone again, it may be time to learn some hard truths about how to start a conversation.

Being a good conversationalist who has mastered the art of chit-chat can help you attract great people, whether romantically, professionally, or even as a new friend. With each new conversation you have, you never know, you might be talking to your future.

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Here are 5 simple habits of naturally great conversationalists:

1. They break the ice

Ready for a cold, hard dose of truth? Starting a conversation is simple. Find someone you want to talk with. Initiate dialogue in a language you both understand. 

Life coach Carolyn Maguire broke it down: "Face the person you want to chat with and stand about an arm’s length away. Approaching someone, rather than passively waiting, demonstrates an initiatory and engaged approach. When combined with other elements of nonverbal communication like a warm smile, appropriate eye contact, and an open posture, it can create a positive first impression and convey social grace."

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When you're done speaking to your chosen person, patiently wait for them to say their part, and the conversation has started. When one of the involved parties stops talking, the conversation is over. 

That completes the technical training on how to start and end a conversation. Simple enough. So why is it so difficult to start conversations?

RELATED: The Art Of Self-Confidence: 5 Simple Habits Of Naturally Self-Confident People

2. They don't live in fear of rejection

Strangers chat with no fear Zamrznuti tonovi via Shutterstock

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We often feel we aren't good enough. "Who am I to talk to her?" we say when we should be saying, "Who am I not to talk to her?"

"Ego effectiveness leads to better relationships," explained life coach Dina Colada. "Ego effectiveness is about aligning yourself with the person you want to be. The more you represent your personal ideal, the more you will like yourself. The more you like yourself, the more confident you will be."

You are good enough, but you have to believe it. We have amazing things to offer because we're amazing people. We need to own this because when we do, we find new conversations are like talking to old friends: effortless.

We need to stop treating people like strangers. Instead, we should view them as friends we haven't yet met. You see someone as a stranger because a voice in your head tells you so, but that stranger wants to laugh, cry, and love just like you. Just like me.

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Deep down, we all want the same things. The people we let slip away are the memories we never make. Fear allows this, but love doesn't.

RELATED: Read This If You're Tired Of Being 'Almost' Good Enough

3. They lead with honesty

There's no right or wrong way to go about this when the intent is genuine. Don't think of the perfect thing to say, because making the effort alone was perfect. You tried. Do you get rejected? So what. That's one less time you'll ever be rejected. Your pride will recover.

We should be thankful for rejection. That's where we get our growth, wisdom, and confidence. Take a chance. Be silly, be kind, be vulnerable, be funny, but most of all, be something, as demonstrated in a study from the American Psychological Association on authenticity and relational well-being.

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RELATED: If You Can Handle Rejection In These 5 Ways, You're More Confident Than 95% Of People

4. They get out of their heads

Conversationalists out of their homes and heads PeopleImages.com - Yuri A via Shutterstock

We view people through a selfish lens, thinking "What can they do for me?" while we should think of how we can be of service to other people. When we get out of our heads and think of others, all of a sudden, the right things to say come easily to us. Once we're available for other people, we're more available for ourselves and don't have to think of what to say.

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From personal experience, change management expert Ruth Littlejohn said, "I realized I knew lots of people, but I didn’t know everything about myself. I got in touch with who I am as a friend — I am introverted (I like lots of time alone to reenergize), I’m a good listener who is OK with silence, and I like to create empowering environments for my friends and me to embrace and explore. Knowing this has helped me attract and support lifelong friends.

RELATED: 12 Low-Effort Ways To Stay Social For Introverts Who Get Exhausted Quickly

5. They know that pretty much every person wants the same thing

So how do you start a conversation? You just do. A study on laughter and relationship well-being supported that every person wants the same thing you want: safety, love, and laughter. Give them that. Give yourself that. You can provide those things because you are those things.

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Talking to the person and getting rejected is a success. Standing on the corner asking "What if?" is the only possible avenue for failure.

RELATED: The Art Of Likability: 9 Psychology-Backed Tricks That Make People Instantly Warm Up To You

Justin McClure is a filmmaker, photographer, digital marketer, content creator, creative director, and author of Pray Your Kids Are Ugly.

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