60 Sample Questions: How to Keep a Conversation Going

Establishing the Groundwork

Before diving into a conversation, lay a solid foundation to keep it going smoothly and engaging. Here are a few tips to help you establish the groundwork:

  • Be genuinely interested in the topic and the other person. People can sense when someone is truly engaged, and this genuine interest will fuel the conversation. For example, if your conversation partner is talking about their recent vacation, be curious about the location, activities they enjoyed, and any memorable experiences they had.
  • Listen actively and attentively to what the other person is saying. Give them your full attention, nod, and make eye contact. This not only helps you to retain and understand the information being shared but also encourages the other person to open up more and feel heard.
  • Ask open-ended questions that allow the conversation partner to share more about their experiences, thoughts, and feelings. Instead of asking questions that can be answered with a simple yes or no, try to encourage elaboration. For example, ask, “What was your favorite part of the trip?” rather than “Did you have a good time on your vacation?” By doing this, you open up opportunities for further discussion and understanding.

Art of Listening

One of the best skills you can develop to keep a conversation going is active listening. Active listening means genuinely focusing on the speaker, their words, and their emotions. Don’t just wait for your turn to speak. Demonstrating that you’re truly engaged in what they’re saying can make the person feel important and build trust.

To become a better listener, try nodding or making small verbal affirmations like “uh-huh” or “I see.” It’s also helpful to practice patience, maintain eye contact, and, if needed, paraphrase or summarize what the person said to ensure you understand them.

Art of Asking

Asking open-ended questions can add depth to a conversation and create opportunities for further discussion. Open-ended questions allow the person to express their thoughts and feelings, instead of simply answering “yes” or “no.”

Examples of open-ended questions include “How did you feel about that?” or “What inspired you to make that choice?” These types of inquiries show genuine interest in the person’s experiences and can lead to more engaging conversations.

30 Sample Questions to Keep a Conversation Going

These questions encourage the other person to share their thoughts and experiences, making the conversation more engaging:

  1. What do you enjoy most about your job?
  2. How do you like to spend your weekends?
  3. What’s something on your bucket list?
  4. What’s your all-time favorite book or movie?
  5. Can you tell me about a memorable experience from your childhood?
  6. What’s the most valuable lesson you’ve learned in life?
  7. What are some hobbies you’d like to get into if you had the time?
  8. What’s been the most challenging project you’ve worked on?
  9. How do you usually handle stress or pressure?
  10. What’s a country you’ve always wanted to visit, and why?
  11. What kind of music do you enjoy, and are there any artists you recommend?
  12. What’s something you’re looking forward to in the next few months?
  13. What’s an accomplishment you are particularly proud of?
  14. How has your taste in books/movies/music/etc. changed over the years?
  15. What’s an important skill you believe everyone should have?
  16. What’s a piece of advice you’ve received that has stuck with you?
  17. What’s a tradition you have with your family or friends?
  18. Can you describe a moment in your life that felt like a turning point?
  19. What’s a subject you wish you knew more about?
  20. What’s a personal challenge you’ve set for yourself recently?
  21. How do you decide what goals to set for yourself?
  22. What’s a fear you’ve overcome, and how did you do it?
  23. What’s a common misconception about your profession?
  24. What’s something that inspires you in your daily life?
  25. What’s a change you’ve made in your life that has had a positive impact?
  26. How do you approach learning something new?
  27. What’s an issue in the world that you’re passionate about?
  28. What’s a habit you’re trying to develop or break?
  29. What’s a piece of technology that has significantly affected your life?
  30. Can you share a story about a random act of kindness you’ve experienced or witnessed?

30 Sample Questions for Deep Conversations

  1. What motivated you to pursue your current career or hobby?
  2. How do you typically overcome challenges that you face?
  3. What’s the most rewarding project you’ve ever worked on and why?
  4. Can you tell me about a time when you had to make a difficult decision? How did you handle it?
  5. What’s a book or movie that has had a significant impact on your life, and in what way?
  6. How do you find inspiration when you’re feeling uninspired?
  7. What’s a lesson you’ve learned recently from an unexpected source?
  8. Can you describe a moment in your life that you would consider a turning point?
  9. What are some hobbies you have that might surprise people?
  10. How do you balance your personal life with your professional responsibilities?
  11. What’s a goal you’re currently working towards, and how are you planning to achieve it?
  12. What’s something you’ve always wanted to learn or do, and what’s stopping you?
  13. What’s the most memorable piece of advice you’ve ever received?
  14. How has your perspective on a certain issue changed over time, and what influenced this change?
  15. Can you share an experience that significantly shaped who you are today?
  16. What’s a challenge you’ve faced in the past that you’re proud of overcoming?
  17. How do you approach making important life decisions?
  18. What’s an aspect of your culture or background that you love sharing with others?
  19. How do you stay motivated when things don’t go as planned?
  20. What’s something you’ve done that took you out of your comfort zone?
  21. What do you think is the key to maintaining strong relationships with others?
  22. Can you tell me about a person who has been influential in your life and how they’ve impacted you?
  23. What’s a skill you’ve developed over time that you’re particularly proud of?
  24. How do you think your friends would describe you, and do you agree with their assessment?
  25. What’s an event in history that fascinates you, and why?
  26. How do you prioritize your mental and physical health in daily life?
  27. What’s a tradition or ritual that you hold dear, and what does it mean to you?
  28. Can you share a moment of unexpected joy you’ve experienced recently?
  29. How do you see your role in your community or society, and what contributions do you hope to make?
  30. What’s a piece of art (music, painting, sculpture, literature, etc.) that speaks to you, and why?

Understanding the Other Party

To keep a conversation going, it’s important to understand the other person’s perspective and interests:

  • Ask open-ended questions to encourage them to share more about themselves. For example, instead of asking, “Did you enjoy your vacation?”, you could ask, “What were some highlights from your vacation?” This gives them an opportunity to elaborate and provide more detail, making the conversation more interesting for both of you.
  • Find common ground by identifying shared interests or experiences. If you discover that you both enjoy hiking, talk about your favorite trails or hikes you’d like to go on in the future. Sharing your own stories that relate to the topic can help deepen the connection and keep the conversation going.
  • Pay attention to non-verbal cues to gauge their level of interest in the conversation. If they seem bored or uninterested, bring up a new topic or ask what they would like to discuss. Being flexible and adapting to their preferences will make them more likely to want to continue talking with you.
  • Be genuinely interested in their life and opinions. People often enjoy talking about themselves, so showing genuine curiosity can lead to engaging and meaningful conversations. Empathize with their experiences and offer your own insight when appropriate. This mutual understanding will create a positive environment for the conversation to flourish.
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Building Rapport Through Empathy

  1. Practicing empathy is a surefire way to keep a conversation going. As you actively listen to the other person, make an effort to understand their perspective. This fosters a comfortable environment and builds trust, which encourages open communication.
  2. For example, when someone shares a story about their weekend, make connections to your own experiences. Say something like, “That must have been so much fun! I went hiking last weekend too, and it was a great way to unwind.” Sharing similar experiences creates a positive atmosphere in the conversation.
  3. Another important element of empathy is acknowledging emotions. If a person talks about a challenging day at work, show understanding by saying, “That sounds really tough. I can imagine how stressful that must have been for you.” Demonstrating that you “get it” will make the other person feel supported, and they’ll likely be more willing to open up.
  4. Asking open-ended questions is also a vital component of empathy. Instead of simple yes/no inquiries, focus on questions that encourage more elaboration and deepen the conversation. For instance, if someone mentions they’ve been cooking a lot lately, ask, “What’s your favorite meal you’ve made recently?” This approach not only demonstrates your interest but also keeps the conversation flowing.
  5. Be mindful of your body language. Maintain eye contact, smile, and nod when appropriate to convey that you’re genuinely engaged with what they’re saying. Non-verbal cues can be just as impactful as words when it comes to building rapport and making others feel comfortable.

Tips and Best Practices

  • Ask open-ended questions: These types of questions allow the other person to elaborate on their thoughts and opinions. For example, ask “What did you do on your vacation?” instead of “Did you go on vacation?”
  • Listen actively: Demonstrate that you’re paying attention by summarizing what the other person says and showing empathy. Nodding your head, maintaining eye contact, and offering verbal cues like “I see” and “Oh, that’s interesting” can go a long way.
  • Embrace silences: Don’t panic when there’s a pause in the conversation. Use this time to reflect on what’s been said and prepare your next question or comment.
  • Express curiosity: If the other person mentions a topic you’re unfamiliar with, ask them to explain or share more information. This can lead to interesting new topics and show that you value their knowledge.
  • Find common ground: Look for shared interests or experiences to build a stronger connection. This might include similar hobbies, travel experiences, or even challenges you’ve both faced.
  • Be mindful of your body language: Keep an open posture and maintain eye contact. Avoid crossing your arms, looking away, or fidgeting as these can indicate that you’re disinterested.
  • Share personal stories: Open the conversational door by revealing something about yourself. When people see that you’re willing to be vulnerable, they may feel more inclined to share their stories too.
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Frequently Asked Questions

What are some tips to maintain a smooth conversation?

To maintain a smooth conversation, you can:

  • Be genuinely interested in the person you are talking to.
  • Find common interests or topics to discuss.
  • Be open-minded and non-judgmental.
  • Use humor to lighten the mood.
  • Maintain eye contact and have a relaxed body posture.

How can I effortlessly switch between topics?

To effortlessly switch between topics, you can:

  • Use transitional phrases like “Speaking of…”, “That reminds me of…”, or “On a similar note…”.
  • If the current topic is no longer engaging, politely steer the conversation towards something else.
  • Be ready with a few backup topics in case the conversation stalls.


Can you suggest some ways to show active listening skills?

To show active listening skills:

  • Maintain eye contact and face the speaker.
  • Avoid interrupting or finishing the speaker’s sentences.
  • Use verbal acknowledgments like “I see,” “That’s interesting,” or “I understand.”
  • Offer feedback and ask follow-up questions.
  • Use body language, such as nodding or leaning in, to show engagement.

What are the common mistakes to avoid in a conversation?

Common mistakes to avoid in a conversation include:

  • Monopolizing the conversation.
  • Interrupting the speaker or not listening attentively.
  • Over-sharing personal information or being too aggressive in asking questions.
  • Being too negative or complaining excessively.
  • Not being open to different perspectives or opinions.

How can I recover if the conversation starts to stall?

If the conversation starts to stall, consider these steps:

  • Ask open-ended questions to revive the conversation.
  • Change the topic to something lighter or more relatable.
  • Share a personal story that connects to the previous conversation.
  • Use humor or a funny anecdote to break the silence.
  • Acknowledge the lull with a lighthearted comment like, “Wow, we really went deep there. Let’s talk about something fun!”.
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