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50 Simple Questions to Ask to Get to Know Someone Deeply

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50 Simple Questions to Ask to Get to Know Someone Deeply

We often meet new people at parties or through work situations. Do you have a good way to get to know someone new without just talking about your job and where you are from?

Usually you are just looking for a pleasant way to pass the time and maybe to find a new friend. So most people know it’s best to avoid talking about politics, religion and sexual orientation. The best way to really get to know someone is to learn what they do (with their spare time) and what they like (probably also shows up in what they do).

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Below are 50 simple questions to ask to get to know someone. It will give you some new ideas for topics to discuss when meeting someone new. Be ready with your own answers too!

Get to know someone by learning what they like

Would you rather…

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  1. Watch Star Wars or Star Trek? Harry Potter or The Lord of the Rings? Use whichever movies you find most relevant.
  2. Read on a Kindle or paperback book? This question is a starter for many possible conversations on reading, favorite books, technology, libraries, bookstores and more!
  3. Go to a play or musical?
  4. Go to the theater or a movie?
  5. Wear jeans or chinos?
  6. Have a Margarita or Pina Colada?
  7. Drink a glass of Guinness or Fat Tire?
  8. Drink coffee or beer?
  9. Crash with friends or stay in a hotel?
  10. Visit Europe or Mexico?
  11. Vacation in Hawaii or Alaska, and why?
  12. Choose a free trip or money? This may tell you whether the person values experiences over dollars.
  13. Stay in a hotel or an Airbnb home?
  14. Go skiing or snowboading?
  15. Travel by plane, train, or automobile?
  16. Enjoy a houseboat or speed boat?
  17. Go climbing or zip lining?
  18. Hike or bike?
  19. Go to a comedy club or dance club?
  20. Have a night out or evening in?
  21. Watch TV or read a book?
  22. Go canoeing or waterskiing?
  23. Camp in an RV or stay in a tent?
  24. Use Facebook or Twitter?
  25. Use iPhone or Android phone?
  26. Win the lottery or find your perfect job?
  27. Swim in a pool or the ocean? Salt water and waves crashing on the beach or temperature controlled, lovely water all year round.
  28. Travel by sailboat or cruise ship?
  29. Watch sports or play sports?
  30. Play dodgeball or kickball?

Get to know someone by learning how they think

  1. Who would you want with you if you were stranded on a deserted island?
  2. If you could do anything you wanted right now, what would it be?
  3. If money was no object, what would you do all day?
  4. Where do you most want to travel, but have never been?
  5. What is your favorite memory?
  6. Who is your favorite author?
  7. What is your favorite book?
  8. Who do you look up to and why?
  9. What was your favorite activity in gym class? (Personally I think the ______ were a lot of fun.)
  10. What has been your biggest challenge?
  11. What is your biggest success up until now?
  12. What does your perfect day look like?
  13. What is one thing that you can’t live without right now?
  14. University or life experience, which do you feel best prepares you for life?
  15. What is the one thing that should be taught in school that isn’t already?
  16. If you were to create a piece of art, what would the subject be?
  17. What one thing would you change if you had to do it over?
  18. If you could go back in time, what year would you travel to?
  19. What does your life say about you?
  20. How would your friends describe you?

How to start the conversation normally

Rather than just asking a question, say: “Movies are fun, but the theater is a richer experience. I recently saw … and loved it. What do you prefer, movies or theater?”

Don’t just go rattle off question after question; let the question you ask naturally lead into a conversation. Once they tell you if they prefer theater or movies, probe into what about their choice that makes it preferable.

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You can even try this communication hack to make the conversation even more natural: Want To Break The Ice And Get Close To Someone Quickly? Try This Communication Hack

Featured photo credit: Unsplash via unsplash.com

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