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36 Questions To Ask Someone To 'Dig A Little Deeper' Than The Surface

Easy ways to keep the conversation interesting.

Cambre Codington

Feb 12, 2019

Syracuse University

1093

36 Questions To Ask Someone To 'Dig A Little Deeper' Than The Surface

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Sometimes getting to know someone can be slightly awkward or even uncomfortable, especially when you get past the basics. Corny, but sometimes 20 questions is the best game to play to get to know someone more than just their name and where they're from. Below are 36 questions to choose from to either ask yourself or ask the person you're trying to get to know.

1. Do you prefer writing with black or blue pen?

2. Would you prefer to live in the country or the city?

3. If you could learn a new skill, what would it be?

4. Do you drink your tea or coffee with sugar?

5. What was your favorite book as a child?

6. Do you prefer baths or showers?

7. If you could be a mythical creature, which would you choose?

8. Do you prefer reading paper or electronic books?

9. What is your favorite item of clothing?

10. Do you like your name? Would you ever change it?

11. Who is a mentor to you?

12. Would you ever want to be famous? If so, what for?

13. Are you a restless sleeper?

14. Do you consider yourself a romantic?

15. Which element best represents you?

16.Who do you want to be closer to?

17. Do you miss someone right now?

18.Tell about an early childhood memory.

19. What is the strangest thing you've ever eaten?

20. What are you most thankful for?

21. Have you ever met someone famous?

22. Do you keep a diary or journal?

23. What is your astrology sign?

24. What do you want your legacy to be?

25. Do you like reading? What was the last thing you read?

26. What is your love language?

27. What are you afraid of?

28. What is your favorite scent?

29. If money wasn't a factor, would you live your life differently?

30. Do you prefer lakes or oceans?

31. If you had to have a tattoo, what would it be and why?

32. Where do you feel the safest?

33. What is one thing you want to overcome/conquer?

34. If you could travel back to any era, which would you choose?

35. Describe yourself using one word.

36. What is your biggest regret and why?

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This article has not been reviewed by Odyssey HQ and solely reflects the ideas and opinions of the creator.

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36 Questions To Ask Someone To 'Dig A Little Deeper' Than The Surface

Easy ways to keep the conversation interesting.

1. Do you prefer writing with black or blue pen?

2. Would you prefer to live in the country or the city?

3. If you could learn a new skill, what would it be?

4. Do you drink your tea or coffee with sugar?

5. What was your favorite book as a child?

6. Do you prefer baths or showers?

7. If you could be a mythical creature, which would you choose?

8. Do you prefer reading paper or electronic books?

9. What is your favorite item of clothing?

10. Do you like your name? Would you ever change it?

11. Who is a mentor to you?

12. Would you ever want to be famous? If so, what for?

13. Are you a restless sleeper?

14. Do you consider yourself a romantic?

15. Which element best represents you?

16.Who do you want to be closer to?

17. Do you miss someone right now?

18.Tell about an early childhood memory.

19. What is the strangest thing you've ever eaten?

20. What are you most thankful for?

21. Have you ever met someone famous?

22. Do you keep a diary or journal?

23. What is your astrology sign?

24. What do you want your legacy to be?

25. Do you like reading? What was the last thing you read?

26. What is your love language?

27. What are you afraid of?

28. What is your favorite scent?

29. If money wasn't a factor, would you live your life differently?

30. Do you prefer lakes or oceans?

31. If you had to have a tattoo, what would it be and why?

32. Where do you feel the safest?

33. What is one thing you want to overcome/conquer?

34. If you could travel back to any era, which would you choose?

35. Describe yourself using one word.

36. What is your biggest regret and why?

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Hopefully they will make you laugh.

1. Why are towels considered dirty when you get out of the shower clean?

2. Who closes the bus door once the bus driver gets off?

3. Why is there a "d" in "fridge" but not in "refrigerator"?

4. If you drop soap on the floor is the floor clean or the soap dirty?

5. Is the "S" or the "C" silent in the word "scent"?

6. Does expecting the unexpected make the unexpected the expected?

7. Would Lightning McQueen buy car insurance or life insurance?

8. Who put the alphabet in alphabetical order?

9. What color are mirrors?

10. If 2 mind readers read each other's minds whose mind are they really reading?

11. Is there a synonym for "synonym"?

12. If your shirt isn't tucked into your pants, are your pants tucked into your shirt?

13. Why is it called "quick sand" if you sink slowly in it?

14. If I try to fail, but succeed, which one did I do?

15. If Cinderella's shoe fit perfectly, why did it fall off?

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