140 Questions to Ask to Keep a Conversation Going

Ever hit that awkward silence and wondered what to say next? Worry no more! With the right questions up your sleeve, you can turn any chat from dull to delightful and keep conversations engaging, fun, and full of surprises. Let’s break the ice!

Ice Breakers

  1. What’s one thing that made you smile today?
  2. Have you discovered any new hobbies or interests recently?
  3. What’s a fun fact about you that not many people know?
  4. Have you watched any good movies or shows lately?
  5. What book or article has caught your attention this week?
  6. If you could only listen to one music artist for the rest of your life, who would it be?
  7. Which season do you look forward to the most, and why?
  8. What’s your go-to comfort food on a rainy day?
  9. Do you have a favorite quote or saying that inspires you?
  10. What’s your preferred way to spend a day off?
  11. Is there a skill or talent you’ve always wanted to learn?
  12. What’s the most interesting place you’ve ever visited?
  13. If you could have dinner with any person in history, who would it be?
  14. Have you taken up any fun projects or DIYs recently?
  15. What would be the title of the movie about your life?
  16. If you could instantly be an expert in something, what would it be?
  17. What do you usually do to unwind after a busy day?
  18. Are there any events or festivals you’re looking forward to attending this year?
  19. If you found a lottery ticket that ended up winning $10 million, what would you do?
  20. Are there any causes or charities you’re passionate about?

Personal Interests

  1. What genre of music can you not go a day without listening to?
  2. Are you into podcasts or audiobooks? What’s the last one you tuned into?
  3. Have you picked up a new hobby that you’re excited about?
  4. Which sport do you enjoy watching or playing the most?
  5. Can you share one of your favorite memories related to your hobby?
  6. Do you have a favorite artist, whether in painting, music, or any other art form?
  7. What’s the most adventurous thing you’ve ever done?
  8. Do you prefer outdoor activities, or are you more of an indoor person?
  9. What’s the last thing you cooked or baked that you were really proud of?
  10. Are there any particular cultures or countries whose art fascinates you?
  11. When you need to feel energized, what’s your go-to activity?
  12. What kind of movies or TV shows can keep you up all night?
  13. Is there a local spot that you love visiting, like a park or museum?
  14. Have you been to any concerts or live performances that blew you away?
  15. What’s the latest project or craft you’ve worked on?
  16. Can you tell me about a tradition that you have with your friends or family?
  17. Are there certain historical eras or events that you find particularly intriguing?
  18. If you had to recommend a book everyone should read, which one would it be?
  19. Do you collect anything, and if so, what sparked that collection?
  20. What kind of technology or app has recently made your life more interesting or easier?

Life Experiences

  1. What’s one childhood memory that you cherish the most?
  2. Can you tell me about a time you felt you truly stepped out of your comfort zone?
  3. What life lesson do you value the most, and who taught it to you?
  4. Have you had a moment in your life that felt like a crossroads? What did you choose?
  5. Can you share a proud achievement of yours, whether big or small?
  6. What’s an unexpected skill you’ve gained from your profession or hobbies?
  7. Have you ever experienced a cultural shock? What was it like?
  8. What was the best vacation you’ve ever taken and why?
  9. Can you think of a particularly challenging time you overcame?
  10. Is there an event or decision in your life that greatly influenced who you are today?
  11. What’s one risk you’ve taken that paid off more than you expected?
  12. Have you ever met someone who turned out to be very different from your first impression?
  13. What’s a tradition from your culture or family that means a lot to you?
  14. Can you describe a serendipitous moment you’ve experienced?
  15. What’s the most valuable piece of advice you’ve received from a mentor?
  16. Have you moved cities or countries and how did that change you?
  17. What’s something you’ve created or built that you’re particularly proud of?
  18. Can you recall a small act of kindness that made a big impact on your life?
  19. What’s a subject you could spend hours talking about?
  20. Have you ever volunteered or done work that felt particularly rewarding?

Aspirations and Dreams

  1. If you could achieve one major goal in the next year, what would it be?
  2. What’s a dream you’ve had since you were a child that you still want to pursue?
  3. What would your ideal job look like if money were no object?
  4. Do you have a vision for the kind of life you want to lead in 10 years?
  5. What’s one skill or hobby you plan to pick up someday?
  6. If you could start your own charity or organization, what cause would it support?
  7. What’s one thing on your bucket list that you plan to check off soon?
  8. Is there a language or culture you dream of immersing yourself in?
  9. Do you have any environmental or sustainability goals for your lifestyle?
  10. What’s an accomplishment that you’re determined to achieve?
  11. Are there any personal development goals you’re currently working towards?
  12. If you could create your own business, what would it focus on?
  13. Do you have any fitness or health-related aspirations?
  14. What invention or innovation do you hope to see in your lifetime?
  15. If you could collaborate with any person or group on a project, who would it be and why?
  16. What’s something that you’re saving up for right now, and how do you plan to use it?
  17. Are there traits or skills you admire in others that you want to develop in yourself?
  18. What’s a cause or issue you feel passionate about and wish to contribute to?
  19. If you could design your dream home, what unique feature would it have?
  20. Do you have any aspirations to travel or live abroad for a time?

Current Events

  1. What’s your take on the latest [topic in news]?
  2. Have you been following [current event]? What are your thoughts about it?
  3. Is there a particular issue in the news that you feel strongly about?
  4. How do you think [recent development or policy] will impact our future?
  5. What’s the most positive news story you’ve heard this week?
  6. How do you stay updated with current events?
  7. Are there any recent scientific discoveries or advancements that you find fascinating?
  8. Do you think social media has changed the way we perceive news? In what way?
  9. What impact do you think [current environmental issue] will have on our planet?
  10. Have you done anything different in your personal life in response to [a recent trend or event]?
  11. Is there a recent movie or book that has reflected current world events interestingly?
  12. How do you feel about the current political climate?
  13. Do you have any predictions for the upcoming [elections, sports season, etc.]?
  14. What’s your opinion on the economics of [a recent change in the market]?
  15. Have you participated in any events or movements recently?
  16. How do you think advancements in technology will shape our lives in the near future?
  17. What do you think about the rise of virtual events and conferences?
  18. With recent events in mind, what do you think our biggest priorities should be as a society?
  19. Is there a current event that you’d like to learn more about?
  20. What changes in your local community have you noticed lately that you find interesting?

Funny and Whimsical Questions

  1. If you could have any animal as a pet, real or mythical, what would it be?
  2. What’s the most hilarious fashion trend you’ve ever followed?
  3. If you were a superhero, what would your superpower and name be?
  4. What would your perfect theme park be like?
  5. If you could only eat one type of cuisine for the rest of your life, what would it be?
  6. Have you ever had any ridiculous nicknames? What’s the story behind them?
  7. What’s the strangest dream you remember having?
  8. If you could swap lives with a character from any TV show or movie for a day, who would it be?
  9. If you had to perform at a talent show, what would you do?
  10. What’s the silliest argument you’ve ever been a part of?
  11. What’s one habit you have that others might find odd or quirky?
  12. What would you name your boat if you had one?
  13. Have you ever believed in any conspiracy theories?
  14. If your life was a genre of music, which one would it be?
  15. If you were an infamous outlaw in the Wild West, what would they call you?
  16. What’s your weapon of choice in a zombie apocalypse?
  17. If you could choose a period in history that be hilariously inappropriate to suddenly time travel to, when would it be?
  18. Have you ever invented a word? What does it mean?
  19. If you could ask your pet 3 questions, what would they be?
  20. In a world where everyone had a theme song that played when they walked into a room, what would yours be?

Deep Dive Questions

  1. What’s a belief you once held strongly that you’ve since changed your mind about?
  2. What do you think are the most important elements of a fulfilling life?
  3. How do you define success, and do you think you’ve achieved it?
  4. What’s the most impactful conversation you’ve ever had?
  5. If you could know the absolute truth on one question, what would you ask?
  6. What’s something you think everyone should do at least once in their lives?
  7. What do you consider your greatest strength, and how has it helped you in life?
  8. How do you deal with uncertainty or the unknown?
  9. Can you think of a book or movie that changed the way you think about something important?
  10. What’s the most valuable lesson you’ve learned from a difficult situation?
  11. How do you approach the concept of work-life balance?
  12. What does empathy mean to you, and can you share a time when it was pivotal?
  13. If you could pass on only one piece of wisdom to future generations, what would it be?
  14. How do you measure personal growth, and what does it look like for you?
  15. Is there a moment in history that you believe has shaped your present in a significant way?
  16. What do you think are the key ingredients for maintaining a healthy relationship?
  17. How do you practice self-care or self-love, and why do you think it’s important?
  18. How does culture influence your identity?
  19. What existential question do you often ponder about?
  20. What do you think is the role of individual action in creating social change?

Frequently Asked Questions

What are some basic tips for keeping a conversation going?

Here are some simple tips to keep in mind:

– Ask open-ended questions: Instead of questions that can be answered with “yes” or “no,” try asking questions that invite the other person to share more.

Listen actively: Show interest in what the other person is saying. Nod, make eye contact, and give feedback like “Oh really?” or “That’s interesting.

Share personal stories: People usually enjoy hearing fun or interesting stories, which could encourage them to open up as well.

How important is it to find common interests?

Finding common interests is like hitting the jackpot in a conversation. It instantly gives you much to talk about and makes the interaction more enjoyable for both sides. 

But it’s not the end of the world if you don’t have a lot in common. You can still have a meaningful conversation by showing interest in what the other person says, asking open-ended questions, and being a good listener.

What are some don’ts when trying to keep a conversation going?

Interrupting: Let the other person finish what they’re saying before you jump in.

Talking only about yourself: A conversation is a two-way street. Make sure to ask questions and show interest in the other person.

Being negative: Keep the conversation light and positive, especially if you’re just getting to know someone.

Any tips for keeping a conversation going in a group setting?

Group conversations can be tricky but also really fun. Here’s how to keep the ball rolling:

Include everyone: Try to engage as many people as possible by asking questions anyone can answer.

Listen and build: Listen to what others say and try to build on it. If someone mentions loving to travel, you can ask, “Has anyone here been to a place they’d recommend for a vacation?”

Know when to step back: In a group, it’s not all about you. Give others a chance to speak and shine.


So, you’ve got the tools; it’s time to use ’em! The next time you’re stuck in a “so, um, how about that weather?” kind of talk, whip out one of these questions. 

Whether you’re curious about someone’s hobbies or dreaming big about the future, these questions will not just keep the conversation going—they’ll make it unforgettable. Happy chatting!

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Robby is a multimedia editor at UpJourney with a journalism and communications background.

When she's not working, Robby transforms into an introverted art lover who indulges in her love for sports, learning new things, and sipping her favorite soda. She also enjoys unwinding with feel-good movies, books, and video games. She's also a proud pet parent to her beloved dog, Dustin.