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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

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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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You'll get an effortless tan

You can exercise with a view

You don't have to worry about bug bites

In n Out all day, every day

We have outdoor concerts

We live where people vacation

Because let's be honest, we all use lyrics.

1. “Don’t get too close, it’s dark inside. It's where my demons hide.”

2. “Tonight, we are young.”

3. “Cuz I may be bad, but I’m perfectly good at it.”

4. “Tell me how they got that pretty little face on that pretty little frame.”

5. “I can’t wait to fall in love with you, you can’t wait to fall in love with me.”

6. “Sweatpants, hair tied, chillin with no makeup on.”

7. “Why you so obsessed with me?”

8. “We ain’t ever getting older.”

9. “I didn’t know that I was starving until I tasted you.”

10. “Didn’t they tell you I’m a savage?"

11. “I’m gonna make you miss me.”

12. "Cheers to the freakin weekend.”

13. “Love’s a game. Wanna play?”

14. “You don’t know about me, but I bet you want to.”

15. “Let’s set each other’s lonely nights, Be each other’s paradise.”

16. “Trippin’ on skies, sippin’ waterfalls."

17. “Wish we could turn back time, to the good old days.”

18. “But you will remember me for centuries.”

19. “Something about you makes me feel like a dangerous woman."

20. “Don’t act like it’s a bad thing to fall in love with me.”

21. “Darling, I’m a nightmare dressed like a daydream.”

22. “Find me where the wild things are.”

23. “I’m high on lovin’ you.”

24. “If you’re gonna be somebody’s heartbreak, somebody’s mistake, if you’re gonna be somebody’s first time, somebody’s last time, be mine.”

25. “Don’t be afraid to take the road less traveled on.”

Everything Bruce says in his classic rock songs.

1. "Talk about a dream Try to make it real You wake up in the night With a fear so real Spend your life waiting For a moment that just don't come Well don't waste your time waiting." (Badlands)

2. "It's a town full of losers/ I'm pulling out of here to win" (Thunder Road)

3. "You've got to learn to live with what you can't rise above" (Tunnel of Love)

4. "I got something in my heart/ I been waitin' to give/ I got a life I wanna start/ One I been waitin' to live" (Leah)

5. “God have mercy on the man/ Who doubts what he’s sure of” (Brilliant Disguise)

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1. "Talk about a dream
Try to make it real
You wake up in the night
With a fear so real
Spend your life waiting
For a moment that just don't come
Well don't waste your time waiting." (Badlands)