Last updated on November 7th, 2023 at 11:09 am

How to make a conversation interesting?

How to make a conversation interesting? It’s actually easier than you think. However, it can be hard when the person you’re talking to isn’t engaging or the topics are boring.

When starting a conversation or attempting to make a conversation interesting, you should always strive to be genuinely interested in the person you’re talking to. It’s also important to be authentic.

So, how to make a conversation interesting without preparing or practicing social skills? We’ll just change how you ask questions. Most importantly, sincerely be interested and ask open-ended questions. That’s it!

Remember, there is no magic question or special skill you need to have. However, we do recommend having a few questions memorized to guide you when talking to people questions and when in different social situations.

Now, the only thing to do starting today is to get better! Below we have several tips you can use to improve how you ask questions and examples of questions to get people to open up and for you to seem more interested.

Lastly, be able to answer simple questions about yourself without hesitation.

You got this! Now, let’s learn how to make a conversation interesting! 

What’s an Interesting Conversation?

An interesting conversation is a dynamic exchange of ideas, emotions, or insights between two or more individuals that engages the mind and stirs the soul. Unlike run-of-the-mill chats that graze the surface of mundane topics, an interesting conversation dives deeper, often unlocking new perspectives or revealing hidden layers of complexity.

A meaningful conversation has the power to challenge established beliefs, kindle curiosity, and even change the course of lives. The participants walk away not just better informed but also enriched, as if they’ve found a new piece to the ever-evolving puzzle of human understanding.

This magical interplay becomes a wellspring of mutual respect and possibly a foundation for lasting connections.

The first step to making a conversation interesting:

Crafting Interesting Conversations: The Power of Great Questions

Embarking on the path to an engaging conversation begins with the seeds you plant—your questions.

Think of it this way: when you ask someone the routine “How are you?” the autopilot response is almost always “I’m fine, thanks.” It’s a conversational dead end. But, when you transform your approach by asking something thought-provoking, something that tickles curiosity, you open a door to a world of possibilities.

Imagine you’re at a gathering, and instead of the usual, you ask, “What’s something you’ve learned this year that changed the way you think?” Such a question does more than invite a response; it invites the other person to share a piece of their journey, to connect with you on a more personal level. It shows you care about more than just surface-level interaction—you’re interested in their experiences, their growth, and their humanity.

Simple, above-average questions can lead to rich, multi-layered conversations. They demonstrate empathy, showing you see the person in front of you as more than just another face in the room. You recognize they have stories worth telling, insights worth sharing, and ideas that might just challenge your own perspectives.

Remember, the goal isn’t to interrogate but to invite a dance of dialogue, a reciprocal sharing that enriches both sides.

So next time you’re about to chat with someone, pause for a moment. Consider what you’d truly like to learn about them, and let your question be a bridge to a memorable conversation.

After all, great conversations start with great questions—and you have the power to ask them.


The 12 Ways to Make Conversation Interesting


Ignite curiosity in your conversations with questions that delve deeper. It’s not just talk; it’s an exploration, a simple yet profound way to connect and uncover the hidden stories that make each of us unique.

Your next great dialogue is just one intriguing question away.


1. Stop asking basic questions, use high quality


Examples of safe and generic questions are “Where are you from?” or “Where did you go to college?”. These are fine to get started but not to keep things interesting.

Also, it’s easy and feels safe to ask generic questions when you’re getting to know someone, or even while catching up with old friends. But, if you want to have a more interesting conversation, and dive deep into people’s lives, a deeper level, it’s important to go beyond the generic and safe questions.

Asking questions about people’s interests, experiences, and passions can reveal a lot more about their personalities. It can create an exciting and engaging conversation both of you can enjoy. Also, take a look at some charming strategies to hold a conversation.

Remember, it all starts with the questions you ask, the tone you use, and also a little bit of a spark, also know as compatibility. 

2. Make the conversation fun and more in-depth

Revitalizing conversations starts with a shift away from the mundane.

Picture this: Instead of the standard “What do you do?” you ask, “What’s the one dream you’re chasing this year?” It’s a simple change that can lead down a path of inspiring stories and shared aspirations.

Now, imagine you’re in a coffee shop. You notice the book someone is reading. “Which book character’s life would you choose to live?” you ask. It’s an unexpected twist that can weave personal dreams with fictional escapades into the fabric of your chat.

And music—rather than the usual “What music do you like?”—try, “If you could listen to only one album for the rest of your life, which would it be?” Such a question can reveal deeper layers of someone’s identity and possibly connect you over a mutual love for a melody.

By choosing these thoughtful questions over the everyday, you’re not just making small talk; you’re crafting an opportunity for a memorable, meaningful connection.

how to small talk to make conversation interesting

3. Adjust conversation starters based on social context

Say you’re mingling at a colleague’s book launch. The room buzzes with literary energy. Instead of the generic “Enjoying the party?”, you could say, “Which book turned you into a lifelong reader?” It’s a question that’s not just relevant but shows you’re attuned to the event’s theme and the interests likely shared by those attending.

In a more personal setting, like a family reunion, consider something heartfelt and reminiscent, such as, “What’s your favorite memory from our childhood gatherings?” It shows a desire to connect on a personal level and appreciate the shared history.

Each conversation is an opportunity to bridge worlds with words. Observe, listen, and then speak with intention. By doing so, you’re not just filling silence, you’re enriching the moment with the possibility of genuine connection. Use your surroundings as a canvas to draw out stories, crafting exchanges that leave both you and your conversational partner with a lingering sense of shared discovery.

Think outside of the box and pay attention to your environment. One way to do this is by observing your surroundings and using them as cues for good conversation topics.

4. Be mindful of people’s feelings and experiences

Inviting stories is an art.

Imagine you’re talking to someone who’s just returned from a trip. Instead of asking “How was your trip?” which often elicits a brief “Good” or “Fun,” you could ask, “What was one unexpected highlight of your trip?” This encourages your conversation partner to share a unique experience, giving them the floor to unfold a tale that’s likely rich with personal insight.

As they speak, be the listener who nods, who asks follow-up questions like “What did that feel like?” or “What did you learn from that?” It’s these kinds of responses that assure them their stories are not just being heard, but felt and understood.

In every conversation, remember it’s a two-way street.

Your aim is to not only convey your own thoughts but to welcome theirs with open arms. Show that their experiences, no matter how grand or small, matter to you. This is what lays the foundation for not just good, but great conversationalists.

It takes mindful practice, but once you make it a habit to engage this way, your conversations will naturally become more vibrant and meaningful. Always be conscious of the impact your words can have; an unconsidered comment can easily dampen the spirit of sharing.

Conversations should be gateways, not just to interesting stories, but to a sense of belonging and being understood.


Get 8 Free Tools to Become Socially Confident

Subscribe to our community and get a HUGE discount on our course, Next Level Conversation

conversation stems

5. Impress people with above-average questions

Crafting compelling questions that spark meaningful conversations can be a challenging endeavor, particularly when put on the spot. Memorizing an array of questions isn’t practical. Instead, lay the groundwork by researching the individual(s) you’ll be engaging with or delving into the specifics of the event at hand.

Above-average questions often require a bit more thought and are tailored to the individual or situation. They go beyond the usual “What do you do?” and instead open the door to more insightful conversations.

Here are some examples:


Personal Growth and Experiences:

  • “What’s a recent challenge you’ve overcome, and what did it teach you about yourself?”
  • “Can you share a pivotal moment in your life that redirected your path?”

Career and Professional Insights:

  • “What’s the most unexpected lesson your career has taught you so far?”
  • “In your experience, what qualities do you think are essential for someone to excel in your field?”

Passions and Interests:

  • “What project or hobby excites you the most right now, and how did you get involved with it?”
  • “When you have an hour of free time, how do you like to spend it, and why?”

Perspectives and Opinions:

  • “What book, movie, or talk has significantly shifted your perspective on an important issue?”
  • “How do you think your field of work will evolve in the next decade, and what do you find most promising about its future?”

Innovation and Creativity:

  • “Can you tell me about a time when you had to think outside the box to solve a problem?”
  • “What’s something you’ve created that you’re particularly proud of, and what inspired it?”

Learning and Education:

  • “Is there a skill you’ve recently learned or are wanting to learn? What motivated you to pick it up?”
  • “In your opinion, what’s a crucial skill or knowledge area that’s commonly overlooked?”

Personal Values and Motivations:

  • “What are three values you strive to embody in your personal and professional life?”
  • “Who has been a significant influence on you, and in what way?”

Industry-specific or Event-specific:

  • “Given the recent developments in [industry/topic], what do you think will be the biggest game-changers over the next few years?”
  • “How do you see the role of [specific technology or trend] impacting our everyday lives?”

Future Goals and Aspirations:

  • “What’s the next big goal you’re working towards, and how did you decide to pursue it?”
  • “Where do you see yourself in the next five years, and what are the steps you’re taking to get there?”

This format can make it easier to navigate through different types of questions and pick the most appropriate one based on the context of your conversation. 


6. Don’t forget to talk about lighter topics too


Navigating the lighter side of conversation can be just as revealing and enjoyable as deep dives.

Strike a chord by inquiring about joys and leisure—like “What hobby brings you the most joy these days?” or “What song always gets you on the dance floor?” Such questions are windows into what lights someone up inside and can often spark a lively exchange.

Dare to be different in your approach, too. A quirky twist like “What’s the most unusual dish you’ve ever tried?” or “If you could be a character in any TV show, who would you be?” can infuse a mundane chat with fun and curiosity.

Remember, the goal is to weave a tapestry of connection that feels effortless and enjoyable.

With each conversation, you’re not just passing time; you’re giving someone the space to share a slice of their life with you. Embrace this chance to learn, laugh, and lay the groundwork for a bond that could last well beyond the initial pleasantries.


“Good conversation is not just about swapping facts. It’s about the uncharted journey where we let curiosity and interest guide us beyond the superficial.”

— Celeste Headlee, Author and Communication Expert


7. Share something slightly personal about yourself

Have you ever found yourself in a conversation that feels more like an interview than a mutual exchange?

The key to captivating dialogues is balance, especially when it’s about personal disclosure. Yes, encouraging others to speak is essential, but revealing a bit about yourself is equally powerful in nurturing a connection.

Let’s say you’re discussing favorite cuisines, and your companion mentions their love for Italian food. Here’s your moment to weave in a personal touch: “I actually tried making homemade pasta last weekend. It was a comedy of errors with flour everywhere, but there’s something magical about creating a meal from scratch, don’t you think?”

By sharing such snippets, you’re not just providing information, but you’re also extending an invitation for empathy and shared experiences. It could prompt your conversation partner to share their own kitchen escapades, forging a bond through the relatable joys and mishaps of cooking.

When you share something personal, you do more than merely inform; you give a piece of yourself. This act of vulnerability, no matter how small, signals to others that you trust them, potentially deepening the relationship. The art isn’t just in the sharing, but in choosing the right moments and the right details that invite warmth and trust.

*Remember, it’s about striking a delicate balance between listening and revealing, which transforms a simple chat into a tapestry of shared human experience. 


8. Asking for Opinions: The Spice of Conversation

Facts have their place in dialogue, but opinions are the secret sauce that gives conversation its flavor.

Want to know a handy trick to turn a mundane exchange into a riveting discussion? Simply seek out someone’s opinion. This tactic doesn’t just keep the conversational ball rolling; it offers a glimpse into the mind and heart of your conversation partner.

Try this on for size: you’re chatting with someone about the latest environmental policies. Rather than just citing statistics, you pivot with, “What’s your take on the new sustainability initiatives?” This not only shows that you value their viewpoint but also opens the floor to a more dynamic and insightful exchange.

Or imagine you’re discussing the hustle and bustle of city life. Instead of a generic comment on the population density, ask, “What’s the charm of city life that keeps you anchored here in NYC?” It’s personal, it invites storytelling, and it paves the way for a discussion rich with personal reflections and perhaps even a shared sense of community.

Asking for an opinion does two things: it shows respect for the other person’s perspectives and it encourages a deeper dive into topics of substance. And who knows, the opinions shared might challenge your own views or introduce you to a fresh way of thinking.

Every opinion holds the potential for a new insight, making the conversation not just interesting but also enlightening.

Get 8 Free Tools to Become Socially Confident

Subscribe to our community and get a HUGE discount on our course, Next Level Conversation

9. Don’t be afraid of being a little random

Now, keep in mind what the social situation is and conversations depend on where you are or what social context it is. So, being a little random means, having fun asking spontaneous questions or talking about odd (appropriate) conversation topics.

Next, use whatever is around you, the event you’re at, and talk about what the other person is wearing to start a conversation. Or, just ask a random question or talk about a random topic. Below are a few examples:

“I love your shoes. Do you mind sharing where bought them?”

“Your lunch looks delicious. Did you make it yourself?”

“Beautiful weather isn’t it? I can’t wait to go to the beach.”

If you say almost anything with confidence you’ll be able to create and start a conversation with momentum. If you want to learn more about social confidence get our free social tools here!

Get 8 Free Tools to Become Socially Confident

Subscribe to our community and get a HUGE discount on our course, Next Level Conversation

10. The most interesting topic is … THEM

One method that will improve conversation skills is something we call the TAT method. It’s a strategy to improve small talk with people which means, Talk About Them. This is an easy way to remember that people like talking about themselves. Talking about them means, exploring who the person you’re talking to is.

Who are they, what do they do, and why are they there?

The questions below are examples of using the TAT method to extend a conversation and take it to a deeper level.

What are some personal projects you’re working on outside of your job?
Any thoughts about today’s meeting?
Did you have any highlight this week?
What are you looking forward to this weekend?

talk about yourself

11. Pick a topic they like: Unlock their passion


Ever noticed how a person’s eyes light up when you steer the conversation toward something they love? That’s your cue for an enthralling discussion. To get there, initiate with easy small talk, then deftly shift gears into their passion zone.

Imagine you’re talking to someone who’s a sports enthusiast. Instead of hovering on the surface with comments on recent games, delve deeper. A question like, “How do you think sports journalism has changed the way we experience games?” can unlock a treasure trove of thoughts and feelings.

This approach does more than make chit-chat; it shows you’re interested not just in the topic, but in their unique perspective on it. 

So find that spark of interest and watch the conversation catch fire.


12. Ask to give advice or ask for advice

Some people think giving advice is a powerful form of engagement between two people. When you offer advice to someone it can show you’re willing, to be honest with them, and that you care about them. In addition, this shows a high level of trust, which creates a more in-depth level of closeness.

More interestingly, asking for advice shows vulnerability and can create intimacy. “One key pattern associated with the development of a close relationship is sustained, escalating, reciprocal, personal self-disclosure,” wrote Psychologist Arthur Aron in his study An Experimental Generation of Interpersonal Closeness. 

For example: 

“I’m having a challenge at work about … what do you think?”

“I’ve had a hard time finding a good place to eat out in the city, what resturants do you suggest going to?”

Example questions to make a conversation interesting

Fun conversation starters, Make things interesting

  1. What is your favorite Netflix show? Tell me about it.
  2. What are some of your future travel plans?
  3. What type of music or songs puts you in a good mood?

Deep Conversation Questions, Get to know someone better

  1. What are some personal projects you’re working on?
  2. What are you looking forward to this weekend?
  3. Tell me more about your family. What was it like growing up in [location]?

If you’re feeling adventurous, A few funny conversation starters

  1. What would your theme song be while walking to work and why?
  2. Which celebrity would you have dinner with and why?
  3. How many days do you think it takes you to scroll a mile on your phone? One day? One week?

Conversations for business, Conversation starters for networking

  1. Have you tried any of the food? What’s good here? What do you recommend?
  2. What did you get done today at work?
  3. I’d love your input on this. Should I have [appetizer #1] or [appetizer #2]? It’s the most important decision I’ve had to make today.

 Casual Conversation Starters, Build a bond with people you meet

  1. How’s your [day/night] going? Going as you expected?
  2. Do you have a go-to conversation starter for these types of events?
  3. Did you hear about how some dinner party hosts are banning small talk? What do you think of that?

Lastly, sometimes the most powerful way to start a conversation is simply saying, “Hi, my name is ______”. Then have an open-ended question ready to go and you’ll start the greatest conversation of your life.

Extra Insight: Elevate Your Conversations

Take a look at two of our posts that go into detail about. 90 conversation starters and more! Click below to view more … 

“I never know what to talk about” The formula & 50+ openers

The best open-ended statement for conversation & 40+ Openers

FAQ’s: Top Conversation Queries Answered!

How can I avoid awkward silences in a conversation?

Answer: Awkward silences can feel like stumbling blocks, but they’re also natural pauses that offer a chance to steer the dialogue in a new direction.

To smoothly bridge these gaps, have a mental list of go-to topics that are universally relatable, like travel, food, or even thought-provoking “would you rather” questions. For instance, “Would you rather have the ability to time travel or speak every language fluently?” Such questions are not only great icebreakers but also open doors to deeper exchanges.


How do I keep a conversation going without it feeling like an interrogation?

Answer: The key to a flowing conversation is a two-way street. After you ask a question and listen to the answer, share a bit about your own experiences or opinions to balance the exchange. For example, if you’ve asked about their favorite book, mention yours too and why it resonates with you.

This encourages a natural back-and-forth dialogue rather than a one-sided Q&A session.


How can I make small talk more interesting?

Answer: Small talk doesn’t have to be dull. Infuse it with personal touches or unexpected angles. Instead of asking, “What do you do?”, you could ask, “What’s something you’ve worked on recently that excited you?” It’s about finding the extraordinary within the ordinary.

This not only makes the conversation more engaging but also shows that you’re genuinely interested in their responses.


How do I engage someone who seems shy or reluctant to talk?

Answer: It’s important to be sensitive to the comfort levels of others. Start with gentle, open-ended questions that invite them to share without pressure. Questions like, “I’d love to hear about your interests; what do you enjoy doing in your free time?” can open a doorway. Show that you’re an attentive listener and give them time to respond.

Your patience and attentiveness can help a reticent conversational partner open up at their own pace.


Summary“How to make conversation interesting” 

“Conversations That Captivate”

To transform any dialogue from mundane to memorable, begin with Active Listening. Make eye contact and nod to convey that you’re not just hearing, but truly listening. When they recount an experience like a mountain trek, prompt further sharing with, “That’s exhilarating! What was the view like from the top?”

Delve deeper with Thought-Provoking Questions. Instead of yes-or-no inquiries, ask, “Who would be your guest at a historical dinner party?” Such questions invite storytelling and reflection.

Share your own tales to encourage a two-way street of sharing with Personal Stories. Relate to their travel anecdotes by recounting, “That reminds me of when I lost my way in Thailand and stumbled upon the most fantastic street market.”

Employ Empathy to resonate with their experiences. When they share a challenge, respond with, “That sounds tough. How are you managing these changes?” It shows you value their feelings.

Lighten the mood with Humor. Share a chuckle with, “I tried salsa once and nearly became a dance floor hazard. Ever had a dance misadventure?”

Forge a bond over commonalities with Find Common Ground. Discovering a shared passion for photography can lead to exchanges about favorite scenes and techniques.

Let your Curiosity shine by expressing genuine interest in their interests, like their fascination with the stars, encouraging a lively exchange about the cosmos.

With Appreciation, acknowledge their achievements. Complimenting their musical skill as “impressive” reinforces their value in the conversation.

Share Resources to extend the conversation beyond the now. Suggesting a book on mindfulness can open up a future dialogue about personal growth.

Engage with Storytelling to create a captivating scene that transports your listener right into a Parisian café, turning the exchange into an imaginative journey.

Always inject a dose of Positivity to keep the conversation uplifting. A little encouragement can go a long way in affirming their endeavors.

And above all, practice Mindful Communication. Be fully present, set aside your phone, and immerse yourself in the world of the conversation at hand.



Get 8 Free Tools to Become Socially Confident

Subscribe to our community and get a HUGE discount on our course, Next Level Conversation

What you can do right now

Download our Tool Kit for free (mini-course, social blueprint, and more) Prepare more when you go out to socialize. We think if you join our community or read a few more blog posts, you won’t be saying, “how to make a conversation interesting.”

But, you’ll feel more confident, and prepared and you’ll know what to do next, especially, when it comes to socializing. 

Steve Anthony

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