201 Actually Interesting Questions to Get to Know Someone

Questions to Ask Someone You Just Met

1. Did you grow up around here or somewhere completely different?

2. What brought you to this city?

3. What’s been the highlight of your week so far?

4. Any go-to coffee or lunch spots here?

5. What kind of music have you been into lately?

6. Do you prefer mornings or nights?

7. Are you more a book person or a movie person?

8. What show or podcast would you recommend right now?

9. What’s one small thing that made you smile today?

10. What hobby have you recently picked up?

11. Favorite weekend ritual?

12. Where’s the best place you’ve traveled to recently?

13. What three words describe your hometown?

14. Do you have any pets? Tell me about them.

15. What’s your favorite way to get exercise?

16. Do you prefer city life or nature?

17. What food would you never get tired of?

18. What app do you open first in the morning?

19. What’s a skill you’re trying to learn?

20. What’s your favorite local view or lookout?

21. Favorite way to spend a rainy day?

22. What’s the last thing that made you laugh out loud?

23. Do you have a favorite quick comfort recipe?

24. What’s a neighborhood gem you love?

25. Do you play any instruments?

26. What’s an underrated thing about where you live?

27. How do you usually meet new people?

28. What’s one local event you never miss?

29. What’s the last live event you attended?

30. Are you more spontaneous or a planner?

31. What’s one thing you want to do this year?

32. Do you prefer tea, coffee, or neither?

33. What’s your favorite podcast episode recently?

34. What’s a book you read this year?

35. What would you show a visitor first in your city?

36. Do you have a favorite lunch order?

37. What’s your favorite emoji to send?

38. How do you unwind after work or classes?

39. What’s your favorite way to learn something new?

40. If you could teleport right now, where would you go?

Personal Questions to Get to Know Someone Better

1. What three words would you use to describe yourself?

2. What nickname do you love or hate?

3. Do you believe in astrology? Why or why not?

4. What’s a childhood dream you still think about?

5. If money were no object, what’s the first thing you’d buy?

6. Does your family have any big traditions?

7. Who is the funniest person in your family?

8. What creative project are you proud of?

9. What do you do when you need inspiration?

10. What’s something you wish you did more of?

11. What would you change about your hometown if you could?

12. What kind of small habit makes your day better?

13. What’s the best gift you’ve ever received?

14. Are you a list-maker or go-with-the-flow person?

15. What’s your favorite holiday and why?

16. What’s your favorite way to celebrate small wins?

17. What was your first job like?

18. What’s a tradition you’ve created as an adult?

19. What’s one talent you’d love to gain overnight?

20. Do you prefer solo travel or group trips?

21. What’s a routine you never skip?

22. Do you prefer same vacation spot or new places each time?

23. What was your biggest childhood hobby?

24. Do you enjoy reconnecting with old friends?

25. What’s an everyday task you secretly enjoy?

26. What would be your dream side hustle?

27. What historical era would you visit for a day?

28. What’s your favorite memory from the past year?

29. How do you prefer to receive appreciation?

30. What small indulgence do you allow yourself?

31. What’s one food you’d happily eat forever?

32. What stereotype about your generation annoys you most?

33. Do you remember your first concert? Who was it?

34. What childhood TV show do you still quote?

35. What’s a weird comfort habit you have?

36. Would you rather have a big party or a quiet dinner?

37. What’s your favorite way to spend a lazy Sunday?

38. Do you believe in fate or free will?

39. What’s one lesson you learned the hard way?

40. Who is someone you admire and why?

Deep Questions to Ask Someone

1. What is something that makes you feel unstoppable?

2. What’s the biggest compliment you can give someone?

3. Would you call yourself brave? Why or why not?

4. When do you feel safest?

5. What is your favorite childhood memory?

6. What’s your biggest regret so far?

7. What are you most grateful for right now?

8. What is a weakness you wish you could fix?

9. What small act of kindness changed your life?

10. What do you look for when choosing new friends?

11. Are you a good gift giver?

12. Do you find it easy to accept help?

13. Who do you admire and what do you learn from them?

14. Have you had a spiritual experience?

15. What breaks your trust quickly?

16. Do you live by a personal mantra?

17. How would you spend your last day on earth?

18. Are you introspective? How often?

19. What is your number one life goal?

20. How do you want people to describe you?

21. Have you ever been in love? What did you learn?

22. Do you want a family someday? Why or why not?

23. How do you define beauty in others?

24. Do you think dreams have meaning?

25. What would you never joke about?

26. What gives you hope on hard days?

27. What makes you genuinely angry?

28. What is your biggest fear?

29. How do you show love to others?

30. What does friendship truly mean to you?

31. Have you had an epiphany that changed you?

32. What lie have you regretted most?

33. What are you most proud of?

34. What emotion do you least like feeling?

35. What’s the toughest conversation you’ve had?

36. What is your biggest insecurity?

37. Do you hold grudges or forgive easily?

38. What makes you envious?

39. Do you consider yourself a people-pleaser?

40. What is your core value that guides decisions?

Fun “Get to Know You” Questions

1. Describe your perfect day.

2. What’s the best cereal? (and why)

3. What movie could you watch every day?

4. What’s your dream career?

5. Which unconventional animal would you want as a pet?

6. Museum or backcountry trail?

7. Which museum would you visit first?

8. What’s the worst song in your opinion?

9. What music genre would you erase?

10. Fly or teleport — which do you pick?

11. What is your claim to fame?

12. What skill have you always wanted to learn?

13. What’s your favorite TV show?

14. All-time favorite food?

15. What do you daydream about most?

16. Do you have a morning routine?

17. What part of your day is the most relaxing?

18. What are you most excited about next year?

19. What would the ultimate theme party be?

20. What’s at the top of your bucket list?

21. What’s the worst job you can imagine?

22. If you could know the future, would you?

23. Most beautiful place you’ve seen in person?

24. What’s the fanciest place you’ve been?

25. Favorite kind of weather?

26. City life or remote retreat?

27. Survive a zombie apocalypse — yes or no?

28. Favorite type of exercise?

29. Which phone app is your go-to?

30. Cook at home or go out — which wins?

Funny Questions to Ask Just for Laughs

1. If you could jump into a pool of anything, what would it be?

2. What’s the best Wi-Fi name you’ve seen?

3. What’s the worst smell to you?

4. Why are pizzas round but boxes square?

5. What part of the driving test would you fail?

6. Do you talk to yourself? In what voice?

7. Are you still scared of monsters?

8. Most embarrassing celebrity crush?

9. Worst pickup line you’ve heard?

10. Would you pick uncontrollable farting or hiccuping?

11. What would be the funniest superpower?

12. What dessert is your best friend’s personality?

13. Weirdest online purchase you ever made?

14. If fruits could talk, which would be funniest?

15. Is a burger a sandwich? Defend your answer.

16. Choose one: eyelashes or eyebrows?

17. If your phone could talk, what would it reveal?

18. If raindrops weren’t a thing, what would fall from the sky?

19. What’s the silliest way you’ve been injured?

20. What would your pet’s voice sound like?

Interesting & Thought-Provoking Questions

1. What’s a mystery you’d love to know the answer to?

2. What everyday decision reveals character?

3. If you could interview anyone from history, who?

4. What recent experience changed your worldview?

5. What should every school teach but doesn’t?

6. Do you think travel changes you permanently?

7. What small habit had the biggest payoff?

8. What would you prototype if you had $10k?

9. Which technological trend worries you most?

10. What’s a public policy you’d change tomorrow?

11. What non-career skill would improve your life most?

12. What book changed how you see the world?

13. If you could fix one global issue, what would it be?

14. What invention would be the most fun to vanish?

15. What scientific discovery fascinates you?

16. How does creativity show up in your life?

17. What would you teach your future grandchildren?

18. Do you think humans will live on other planets?

19. What’s the best decision you’ve made this decade?

20. What question would you ask an advanced AI?

Good Questions to Ask Over Text or DMs

1. What show are you binge-watching right now?

2. If we had unlimited budget for our next hangout, what would we do?

3. What song describes your mood tonight?

4. What’s one small win you had today?

5. What snack should I bring when we hang out?

6. If I dared you to send a selfie, would it be cute or chaotic?

7. What’s the last thing that made you laugh aloud?

8. What movie should I absolutely watch this week?

9. Do you prefer voice notes or text?

10. If I texted “come hang out,” would you?

11. What’s one question I should ask you that I haven’t yet?

External Authority & Further Reading

• Psychology Today — practical communication and curiosity research. (https://www.psychologytoday.com).

• Gottman Institute — relationship research and conversation tools. (https://www.gottman.com).

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