People love to talk about themselves. Studies show that talking about oneself activates the same parts of your brain as food, drugs, and sex! 

Self-disclosure (and getting other people to open up) is scientifically proven to make you more likable and help you form deeper social bonds.

So how do you get past boring small talk and into the good stuff? 

The secret to threading conversation into something deeper is simply asking others excellent questions. 

Open-ended questions are beneficial for learning more about somebody because they may evoke a story. However, you can also use follow-up yes/no questions with “why” or “tell me more” to encourage people to elaborate. 

Here are 250+ juicy and thought-provoking conversation starters to get to know someone better and (hopefully) create an intriguing and memorable conversation. 

Random Questions to Ask Your Friends About Their Interests

When you’re trying to bridge the gap between small talk and deep conversation, the most accessible place to start is asking about what someone likes. 

  1. What’s the best birthday party you’ve ever had?
  2. Where is your favorite place you’ve ever visited?
  3. How do you like to spend your free time? 
  4. What’s one of your favorite bands?
  5. What is the cutest animal you’ve ever seen in person?
  6. How would you describe your style?
  7. If your wardrobe could only be one color, what would it be? 
  8. What was the first concert you ever went to?
  9. What is the best book you’ve ever read?
  10. What’s your favorite movie of all time? 
  11. What’s the stupidest movie or TV show you’ve ever seen?
  12. If you could only have one food for the rest of your life, what would you choose?
  13. What are your biggest pet peeves?
  14. Are you more into brains or looks?
  15. Do you celebrate any holidays? What’s your favorite?
  16. What’s your guilty pleasure? 
  17. Which meal is your favorite: breakfast, lunch, or dinner?
  18. What do you do when you want to chill out after a long day?
  19. How would you spend your ideal weekend?
  20. Do you listen to podcasts, or mostly just music? What’s your favorite podcast?
  21. Do you prefer to go to the movies or watch movies at home?
  22. What was your favorite TV show growing up?
  23. What’s your favorite TV show now?
  24. How would you spend your birthday if money was no object? 
  25. What’s your favorite season? What do you love most about it?
  26. Do you prefer camping or going to the beach? 
  27. Which phone app do you think you use the most?
  28. Would you instead cook, order delivery, or go out to eat? 
  29. How do you drink your coffee?
  30. If you could have any animal as a pet, what would you choose? 
  31. Do you enjoy being alone? How do you spend your alone time?  
  32. What is your biggest pet peeve?
  33. Are you more of an extrovert or introvert? 
  34. How would your closest friends describe you? 
  35. When you’re in a bad mood, is there something or someone that can instantly make it better? Who or what?
  36. What is the best gift you’ve ever received? 
  37. What is your favorite part of your daily routine? 

We created a FREE conversation starter app just for you! Our goal is to help all fellow recovering awkward people. The team put together 1,000 of the best conversation starters on a simple app you can reference in the car or bathroom on your way in:

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Take 1000+ Conversation Starters to Go – FREE!

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Yes or No Questions to Ask Your Friends

For a quick introduction to someone, yes/no questions are low-pressure and leave room for elaboration. These are also quick-fire ways to get to know someone quickly. 

Want to have fun? Answer at the same time and see if your answers match!

  1. Have you ever kept a journal? 
  2. Do you have a best friend?
  3. Do you pay attention to the news?
  4. Have you ever gotten a speeding ticket? 
  5. Do you live alone?
  6. Do you have any kids?
  7. Do you like your job?
  8. Did you ever go to college?
  9. Have you ever been on TV?
  10. Do you believe in ghosts?
  11. Do you like cilantro? 
  12. Do you ever talk to yourself in your head?
  13. Do you sing in the shower?
  14. Have you ever had deja vu? 
  15. Do you believe in aliens?
  16.  Do you like chocolate?
  17. Do you own bitcoin? 

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Questions to Ask People About Their Job

Asking someone about their job doesn’t have to be super bland. There is a lot more to a career than meets the eye. Use these questions to understand more about someone’s interests, motivations, and goals in the professional realm. 

However, if someone clarifies that they don’t enjoy their job (for example, they give concise answers or make negative comments), you may want to move on to a different topic of conversation or only focus on questions related to their dream job or future aspirations. 

  1. What do you enjoy most about your career?
  2. What was your greatest accomplishment in the past year?
  3. What motivates you to work hard at what you do? 
  4. How long have you been doing this job? 
  5. What was your first job? Did you enjoy it?
  6. How do you define success?
  7. What’s your least favorite thing about your job? 
  8. Have you ever had “imposter syndrome”? What did you do about it? 
  9. Would you instead make a lot of money at a job you hate or make less money doing something you love? 
  10. Are there any exciting projects you’re currently working on?
  11. Do you prefer working remotely or in an office?
  12. What career did your parents try to get you to pursue?
  13. Is your career path the same as your college degree?
  14. What does the average week look like for you?
  15. Do you prefer a time-block schedule or a simple to-do list?
  16. What are your career aspirations?
  17. What is one job you’ve always wanted to try?
  18. Do you think your personality matches your current job?
  19. What was the worst interview you ever had?
  20. Where do you see yourself professionally in the next 5 or 10 years?
  21. When you were a kid, how did you answer the question, “what do you want to be when you grow up?”
  22. Did you ever expect yourself to end up in the job you have now?
  23. Do you consider your job fulfilling? Why or why not?
  24. Do you think it’s possible to have your passion and job be the same thing?
  25. What is the wisest business advice someone has ever given you?
  26. Who do you admire most in your professional circle?
  27. Who was the most influential mentor in your career so far? 

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Questions to Ask Your Friends About Yourself

See how well your friends know you with fun questions about yourself and their perception of you.

  1. How would you describe me in 3 words?
  2. What was the first thing you thought of me when we met?
  3. What’s the most annoying trait I have?
  4. Where do you see me in five years?
  5. What attracts you to people? 
  6. What is my favorite food?
  7. What job do you think I would be perfect for? 
  8. Where can you always find me?
  9. What is the most fun memory we’ve had during our friendship? 
  10. Do you know my middle name?
  11. Do you know about my birthday?
  12. What’s my favorite color? 
  13. If I called you in the middle of the night, would you pick me up?

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Questions to Ask About Hobbies

How someone spends their leisure time is an essential clue as to what kind of person they are. Asking a passionate person about their hobbies can get them talking. 

These questions are broad openers that you should follow up with more topic-specific questions if someone has a particular hobby that they are excited about. 

  1. What are you passionate about outside of work?
  2. If you had unlimited free time, how would you spend it?
  3. Do you have any hobbies?
  4. What do you do for fun? 
  5. How did you get into your hobby? 
  6. What lights you up about your hobbies?
  7. Do you collect anything?
  8. What’s your favorite sport?
  9. Have you ever been in a sports league? 
  10. Do you think hobbies are important? 
  11. Would you consider yourself a creative person?
  12. Have you ever tried a creative endeavor like painting, writing, or acting?
  13. Do you like to sing or dance?
  14. What hobbies did you try as a kid? Which ones did you love and which did you despise?
  15. What is your idea of a perfect vacation?
  16. What’s your favorite type of workout or exercise? 
  17. What is your favorite thing to learn about?

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Funny Questions and Weird Questions to Ask Your Friends

Research shows that shared laughter brings people together. If you’re looking for some lighthearted conversation or opportunities for witty banter, these questions let you explore your goofy side. 

  1. Have you ever waved at someone thinking you know them, only to realize they are the wrong person? 
  2. Do you eat or drink soup?
  3. What is a song you pretend you don’t like because it’s embarrassing to enjoy it? 
  4. Have you ever tried to look cool in front of someone and failed?
  5. What’s the strangest thing you’ve seen someone do in public? 
  6. When was the last time you had a big fail moment? 
  7. If you could live anywhere in the world but had to stay naked all the time, where would you choose?  
  8. What voice accent impersonations can you do (British, Australian, country, etc.)? 
  9. What’s your favorite corny joke?
  10. Have you ever tripped or fallen in front of a vast crowd?
  11. What is the weirdest fact you know?
  12. What is the strangest joke someone has asked you? 
  13. If you could have one useless superpower, what would it be?
  14. Which sport would be funniest if it had mandatory alcohol?
  15. If animals could talk, which would be the most sarcastic?
  16. What is one thing that people consider trashy but you consider classy?
  17. What’s the most awkward first date you’ve ever been on? 
  18. What’s your favorite white elephant gift?
  19. Where is the worst smelling place you’ve ever been? 
  20. What is the most fruitless talent you have? 
  21. If you got banned from the library, what would be the reason behind it?
  22. Do you think penguins have knees?
  23. Why is it called lipstick if it doesn’t stick your lips together?
  24. What’s the silliest way you’ve accidentally injured yourself?
  25. What would be the worst bio for a dating app? 

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Questions About Family

Family relationships and upbringing have a significant impact on who people become as adults. Showing interest in someone’s family demonstrates that you want to get closer to them and understand their origins.   

  1. Who is your closest family member?
  2. Do you have a best friend that you talk to daily?
  3. What kind of relationship do you have with your parents? 
  4. How much time do you usually spend with your family?
  5. Who in your family do you most enjoy being around, and why?
  6. Which family member cooks the best food?
  7. What’s the most challenging part about spending time away from your family?
  8. Do you have any siblings? Tell me about them?
  9. Are you close with your brother(s)/sister(s)? What drives you crazy about them?
  10. Do you ever wish you had more or fewer siblings?
  11. Who gives the best gifts in your family?
  12. Which holiday did you celebrate most with your family when growing up?
  13. What’s your favorite story your grandparents have told you?
  14. Have you ever looked into your family lineage? Do you know anything about your ancestry?
  15. What is your favorite childhood memory?
  16. What is the best piece of advice your grandparents or parents have ever given you?
  17. Were you a rebel or an obedient kid growing up? Did you hide things from your parents?
  18. How would you describe your family now?
  19. Does anyone in your family have a nickname for you?
  20. What’s your favorite tradition in your family?
  21. What will always bring your family together?
  22. Is anyone in your family a “character”? What makes them so unique?
  23. Who is the “black sheep” of your family?
  24. Do you think friends or family are more important?
  25. How do you deal with arguments in your family?
  26. What’s something your family doesn’t know about you?
  27. Do you look more like your mom or dad?
  28. Do you know how your parents met?
  29. What was your favorite story your family members told you as a kid?
  30. What was the most challenging part about growing up in your family?
  31. What are you most grateful for about your family?
  32. Who in your family makes you feel the safest?
  33. Is there a particular food your family always makes when they get together?
  34. What kind of music does your family listen to? 
  35. What was the house like that you grew up in? 

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Questions About Values and Goals

Finding out someone’s morals and values is more complex than simply asking, “what are your values?” You can get to the root of what someone believes in by asking things about their motivations, life philosophies, and what drives them forward daily. 

It is also helpful to ask some thought-provoking questions about hypothetical scenarios like “If you could time travel, what time period would you go to?” This allows them to talk about their values in a hypothetical situation without feeling pressured to reveal more profound stories if they don’t want to.

  1. How do you hope people feel when they’re around you?
  2. What are the most important values that you have always stood by?
  3. How would you define a “good person”? 
  4. What are the most essential qualities you want in a friend?
  5. What life lessons did you have to learn the hard way?
  6. If you only had one of your five senses, which one would you choose?
  7. Have you ever volunteered?
  8. What are causes important to you? 
  9. Who do you admire the most and why?
  10. What is your life motto or mantra?
  11. What was your most proud accomplishment in the past year?
  12. If you could choose one thing that would make the world better, what would it be?
  13. Do you believe in astrology? Why or why not?
  14. What is your astrological sign?
  15. Do you believe in giving people second chances?
  16. How can someone earn your trust?
  17. What has someone done to lose your trust?
  18. Do you believe in aliens or life on other planets?
  19. What do you think about manifestation? Have you ever tried it? 
  20. Do you have vivid dreams? 
  21. Do you think dreams have a deeper meaning?
  22. Where have you always dreamed of going?
  23. Do you believe you should do one thing every day that scares you?
  24. What does getting out of your comfort zone look like for you?
  25. How do you define beauty in a person or life?
  26. What is a boundary you have that you’ve always upheld?
  27. What boundary do you have a more challenging time reinforcing?
  28. What do you think holds people back the most from achieving their goals and dreams?
  29. When you want to give up on something, what keeps you moving forward?
  30. When was the last time you had a regret?
  31. Do you live by any particular words of wisdom?
  32. Is it easy or difficult for you to accept help from people?
  33. If money were no object, what would you devote your life to? 
  34. Have you ever wanted to start a business? What kind would it be and why?
  35. If you could live forever, would you want to? Why?
  36. If you could time travel, what period would you go to?
  37. If you could go back in history and spend a day with one famous person, would it be?
  38. Do you have a vision board? If so, what is currently on it?
  39. A genie in a bottle randomly gives you three wishes– what are they?
  40. If you could live anywhere in the world, where would you choose? Why?
  41. If you found out today was your last day on Earth, how would you spend it?
  42. If you find yourself stranded on a deserted island, what three things would you want to have with you? 
  43. What is your number one goal for the coming year?

Pro Tip: There is a certain balance you have to strike between expressing interest in someone versus being too nosey. You don’t want to violate their privacy or go too deep too quickly. 

It’s usually best to steer clear of certain types of questions early on in a friendship: for example, “who did you vote for?”, “what are your religious beliefs?” or “what’s the worst thing that ever happened to you?” are probably best saved for someone you’ve known for a while. 

On the other hand, if you notice someone is sharing more about themselves, move on to more profound questions like the ones below.

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Juicy Questions About Romance and Relationships

Finding out about someone’s perspectives and experiences with relationships is a powerful way to get a little closer to their heart. But there is a time and place for everything. 

It’s best to avoid asking these questions to professional colleagues, new acquaintances, or on a first date. Instead, dive into the relationship realm with friends and significant others that you’ve known for a little while. 

  1. Have you ever been in love?
  2. What is the most attractive quality in a man/woman?
  3. Do you’re a good kisser? 
  4. What is your idea of a perfect date? 
  5. Do you believe in love at first sight? 
  6. What was it like the first time you met your significant other? (if they have one) 
  7. Do you think people fall in love because the right person shows up or because the time in their life is right? 
  8. What did your past relationship teach you?
  9. Do you believe in soul mates? Why or why not?
  10. Would you ever take somebody back who cheated on you? 
  11. Would you uproot and relocate your life for someone you love? 
  12. What is a relationship deal-breaker for you?
  13. Do you ever want to have a family of your own someday?
  14. Have you heard of love languages? What is your love language?
  15. What is your favorite book or romantic movie?
  16. What is the sweetest thing anyone has ever done for you?
  17. Which is more romantic: flowers and gifts or a candlelit meal?
  18. Do you think that people meet for a reason or by chance?
  19. What’s the best advice an older person has ever given you about relationships?
  20. How do you get over heartbreak?
  21. How old were you when you had your first boyfriend/girlfriend?
  22. What are your top 3 most essential qualities in a romantic partner?
  23. What is the longest relationship you’ve been in? 

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Deep Questions to Ask Your Friends

When you want to get to know someone deeper, it is often helpful to open up about your own stories and viewpoints.

Psychologists have found that an equal amount of give-and-take is essential to make both people in a conversation feel comfortable to disclose more intimate details about their lives.

However, over-sharing can lead to awkwardness or embarrassment. Self-disclosure requires trust that you can only build through time and conversation. So only dig into these types of questions once you’ve already started to form a relationship with somebody.

  1. How would you title this chapter of your life? 
  2. If you only had one month left to live, how would you spend it? 
  3. What is the best advice someone has ever given you? 
  4. What makes you feel alive?
  5. Do you typically follow your heart or your head?
  6. What are you most grateful for in your life? 
  7. If you could go back and change one thing about your past, what would it be? 
  8. Which is more critical – beauty, power, or money? 
  9. What’s your biggest fear?
  10. What makes you feel unstoppable?
  11. What is your biggest regret?
  12. Do you think people are mostly good or mostly evil? Why? 
  13. Where do you go when you need fresh inspiration?
  14. What’s your philosophy on life?
  15. Do you like diving into the deep end or easing your way into the water? (literally or figuratively)?
  16. What life-changing events have you experienced? 
  17. What’s one thing you would change about yourself? 
  18. Have you ever had a moment of deja vu? 
  19. What legacy do you want to leave on Earth once you’re gone? 
  20. What gives you hope? 

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Key Takeaways: How to Drive Conversation with Intriguing Questions

Everyone has differing levels of how much they’re willing to open up and share. Fortunately, there is a lot of ground to cover between “how was your day?” and “have you ever been in love?”

There are hundreds of questions you can ask someone without getting ultra-vulnerable, awkward, or nosey. Reading people’s body language and conversation cues is a great way to know what kinds of questions you want to ask next. 

A reciprocal give-and-take can make for an excellent deep conversation that brings you closer to your friends. 

If you want to become an expert conversationalist, Learn the 3 Steps to Amazing Conversation.

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