How to Start a Conversation?… And keep it going?

Last Updated on 2 days by Saiful Islam

Let’s face it: conversations can be a battlefield. For some, they’re a natural jousting match, witty repartee flowing effortlessly. For others (myself very much included), conversations can feel like navigating a minefield – one wrong step, and you’re met with an earsplitting explosion (read: awkward silence).
Starting a conversation is one of those life skills that can feel like a superpower when you’ve mastered it, but for many of us—especially introverts—it can be a bit of a challenge.

I wouldn’t call myself painfully shy, but initiating conversations and keeping them going used to be my Achilles’ heel. Small talk felt like a foreign language, and meaningful connections seemed like a distant dream.
I’ve spent much of my life feeling anxious about approaching people, not knowing what to say, and worrying about awkward silences.
But here’s the good news: conversation is a skill anyone can learn and improve. It’s not about being the most outgoing person in the room. Introverts have unique strengths—like active listening and thoughtfulness—that can make us excellent conversationalists once we know how to leverage them.
So, if you, like me, ever find yourself staring blankly at someone, wondering what to say next, fear not! This guide is for you. I’ll walk you through practical, easy-to-apply tips that have helped me feel more comfortable and confident in conversations.

Why Starting a Conversation Can Be Difficult

Let’s face it—starting a conversation can be tricky, especially for introverts or shy people. We tend to overthink things. “What if I say something wrong?” or “What if they’re not interested in what I have to say?” are questions that run through my mind more often than I’d like to admit.

For introverts, there’s also the added challenge of social energy. Conversations can feel draining; sometimes, we’re not in the mood for small talk.

But the truth is, improving your social skills and learning how to start a conversation opens up new personal and professional opportunities for relationships. It’s worth stepping out of your comfort zone every once in a while.

Key Principles for Starting a Conversation

Before diving into specific tips, I’ve learned a few key principles that have helped me become better at starting conversations. These principles are the foundation for any good interaction.

1. Confidence and Approachability

Even if you’re nervous, appearing confident and approachable can make a big difference. Simple things like maintaining eye contact, smiling, and having an open posture can signal to others that you’re open to talking. It doesn’t mean you have to be the life of the party—just being present and approachable can go a long way.

2. Active Listening

One of the best conversation tools an introvert can have is active listening. This means genuinely paying attention to what the other person is saying instead of worrying about what you’ll say next. Listening closely makes it easier to respond thoughtfully, which helps the conversation flow naturally. Plus, people appreciate being heard!

3. Empathy and Engagement

Empathy and genuine interest in the other person’s perspective are key to meaningful conversations. Ask yourself, “How can I connect with this person?” By engaging with them and showing that you care about what they’re saying, you’ll find that conversations become more enjoyable and less of a chore.

Breaking the Ice: How to Start a Conversation

Starting a conversation doesn’t have to be complicated. Here are a few strategies that have worked for me.

1. Use Open-Ended Questions

Asking open-ended questions is one of the easiest ways to start a conversation. These questions can’t be answered with a simple “yes” or “no” and encourage others to share more about themselves.

For example, instead of asking, “Did you have a good weekend?” (which could lead to a dead-end “yes”), try asking, “What was the best part of your weekend?”

Some other examples include:

• “What’s something you’ve been working on lately?”
• “What’s your favorite way to spend your free time?”
• “What’s been the highlight of your week so far?”

By asking open-ended questions, you give the other person a chance to talk about something they care about, making the conversation flow more easily.

2. Comment on Your Surroundings

This is a great tip for when you’re at a social event or out in public. I’ve found that commenting on your surroundings is a natural way to start a conversation without feeling forced.

For example, if you’re at a coffee shop, you might say, “This place has great coffee—do you come here often?” Or at a social event, “It’s a pretty interesting event. What brought you here?”

The key is to make your comment relevant to the situation, which helps break the ice and feels less intimidating than diving straight into personal questions.

3. Compliment or Acknowledge Something About the Person

People generally respond well to compliments, especially when specific and genuine. Complimenting someone’s outfit, asking about a book they’re holding, or mentioning something you noticed about them can be a great way to start a conversation. For example:

• “I love your shoes! Where did you get them?”
• “That’s a cool phone case—do you have any recommendations for a good one?”
• “I noticed you were reading [book title]. How are you finding it?”

Acknowledging something about the person shows that you’re paying attention and creates an easy entry point for conversation.

How to Start a Conversation in Different Situations

Not all conversations are the same. Here are some tips for starting conversations in different scenarios:

1. Starting a Conversation with a Stranger

Starting a conversation with a stranger can feel intimidating, but it doesn’t have to be. One technique I’ve found helpful is to use the “context-comment-question” strategy. This involves commenting based on your shared environment and following up with a question.

For example, if you’re at a park, you could say, “The weather is beautiful today, isn’t it? Do you come here often?”

This approach works because it’s low-pressure and situational. It’s also a great way to ease into a conversation without feeling awkward.

2. How to Start a Conversation in a Group

Group conversations can be even more nerve-wracking for introverts, but the key is to focus on listening first. I’ve found that observing the group and listening to what’s being discussed allows me to find a natural way to join in.

You don’t need to dive in with a bold statement—sometimes, a simple “That’s interesting, I’ve never thought of it that way” is enough to start contributing to the conversation.

3. Starting a Conversation Online or Over Text

Starting conversations can feel different, but the same principles apply. You can start with a simple comment or question, whether it’s social media, email, or a messaging app.

For example, on LinkedIn, you might say, “I saw your recent post about [topic]. I’d love to hear more about your thoughts on it.”

The key to online conversations is being direct but polite. People often appreciate when you acknowledge something specific they’ve shared, as it shows genuine interest.

Conversation Starters for Introverts

If you’re an introvert like me, having a few go-to conversation starters can make a huge difference. Here are some of my favorites:

• “What’s something interesting you’ve learned recently?”
• “What’s your favorite way to unwind after a long day?”
• “Have you been working on any fun projects lately?”

These conversation starters are designed to go beyond small talk and discuss topics that people enjoy. They’re low-pressure and encourage the other person to share more about themselves, which makes it easier for you to follow up.

Conversation Tips for Shy People and Introverts

If you’re shy or introverted, here are a few additional tips that have helped me improve my conversation skills.

1. Start Small

You don’t have to start with extensive, high-stakes conversations. I began practicing with people I felt comfortable with, like coworkers or neighbors. Small interactions, like chatting with a cashier or saying hello to someone in your building, can help you build confidence over time.

2. Practice Active Listening

I can’t stress this enough: listening is your superpower. When you actively listen, you take the pressure off yourself to constantly come up with things to say. Plus, it makes the other person feel valued, which leads to better, more meaningful conversations.

3. Embrace the Silence

One of my biggest fears used to be awkward silence. But over time, I’ve learned that silence is a natural part of any conversation. Instead of rushing to fill the gap, I pause and reflect before responding. It gives me time to think and makes the conversation feel more relaxed.

Common Mistakes to Avoid When Starting a Conversation

It’s easy to make mistakes when you’re nervous, but recognizing these common pitfalls can help you avoid them:

• Talking too much about yourself: Try to keep the conversation balanced. Ask questions and show interest in the other person’s experiences.
• Overthinking every word: Conversations can be imperfect. Just focus on being present and engaged.
• Ignoring body language: Pay attention to the other person’s nonverbal cues. It might be time to shift the topic or let the conversation wind down if they seem disinterested or uncomfortable.

How to Keep the Conversation Going

Once you’ve started a conversation, the next challenge is keeping it going. Here are a few techniques that have helped me:

• Ask follow-up questions: If someone mentions they’ve been working on a project, ask, “What part of the project do you enjoy the most?”
• Share your experiences: Be bold and share your thoughts or personal stories about the topic. Just remember to keep it balanced and not monopolize the conversation.
• Show genuine interest: People appreciate it when you take an interest in their opinions and experiences. Respond with curiosity and ask questions that allow the conversation to go deeper.

Frequently Asked Questions (FAQ)

What’s the best way to approach someone and start a conversation?

The best way to approach someone is to be confident and approachable. Start with a simple comment or question based on your surroundings or something relevant. For example, if you’re at an event, ask about what brought them there or comment on the atmosphere. Use open-ended questions to encourage more dialogue.

How can I overcome the fear of starting a conversation with strangers?

Overcoming the fear of starting conversations takes practice. Start small by engaging with people in low-pressure environments, like chatting with a cashier or someone in a waiting room. Focus on active listening and remember that most people appreciate a friendly conversation. The more you practice, the less intimidating it becomes.

What should I do if a conversation feels awkward or forced?

If a conversation feels awkward, don’t panic! Try shifting the topic with a new question or comment that’s related but moves the conversation in a different direction. Sometimes, acknowledging the awkwardness with a lighthearted comment can also help ease the tension. Silence isn’t always ominous, so allow pauses without feeling pressured to fill them.

How can introverts improve their conversation skills?

Introverts can improve their conversation skills by focusing on their strengths, such as active listening and empathy. Start by practicing with people you feel comfortable with and gradually expand to more social situations. Be prepared with a few conversation starters, and give yourself permission to take breaks when you feel overwhelmed.

How do I keep a conversation going once it’s started?

To keep a conversation going, ask follow-up questions based on what the other person has shared. You can also offer your insights or experiences related to the topic. Stay curious and engaged in the other person’s words, and avoid dominating the conversation.

Final Thoughts

Starting conversations as an introvert can feel challenging, but it’s a skill you can improve with practice. Active listening, asking open-ended questions, and embracing silence can make your conversations more enjoyable and less stressful.

Remember, it’s not about becoming the most talkative person in the room—it’s about connecting with others in a way that feels authentic to you.

These tips will help you start and maintain meaningful conversations, whether in a social setting, online, or just chatting with a neighbor.

Now, go forth and conquer those conversations! Remember, even the most confident conversationalists were once conversation klutzes. We’re all in this together.