15 Questions To Ask If You Want To Truly Get To Know Someone

Meeting people can be exciting, scary, terrible, or awkward depending on how well you can connect with them. The easiest way to form a strong connection with someone is by getting to know them in a more meaningful way. Here are some questions that can help you learn a lot about who a person really is.

  1. What has your life been like? Whether it’s your first date or you’ve known them for quite some time, you can get a lot of information about a person by asking them to tell you about their life. They can choose the parts of their story they want to share with you and you’re sure to get a meaningful answer.
  2. How important is honesty to you? Some people believe that honesty is the best policy, while others feel that some lies are necessary. How a person feels about truth-telling can give you a clear picture of their personal philosophy and let you know in what ways it differs or tallies with yours.
  3. What is your approach to dealing with conflict? People have different ways of coping with difficult emotions or situations. I’m extremely non-confrontational and would rather bottle everything up until it explodes. Someone else might prefer to deal with issues as they arise or shut down or lash out. Either way, knowing the answer to this question helps you know them better.
  4. Is there something you wish you could do or were better at? This is a really broad question to which there are no right or wrong answers, but if the person opens up, you can see who they really are in how they talk about that thing they’ve been dying to do.
  5. What does friendship mean to you? Knowing what a person values most in the close relationships that they form paints a detailed image of who they are, the things that are important to them, and how they treat their friends.
  6. Are there any special people or things in your life? Ask them to tell you about the people or things that they hold dear and observe their tone and body language as they do so. It is wonderful to see the light come on in someone’s eyes as they talk about the people who mean the world to them.
  7. What are you passionate about? This allows for a very interesting conversation that can offer true insight into someone’s personality. People are usually excited to talk about the things they love doing and they tend to feel closer to people they can share this passion with.
  8. What’s your dream job? If you truly want to get to know someone, then asking them about their dream job would reveal plenty about their priorities. It could be a job that allows more room for creativity, one that pays loads of money, one that is people-oriented, or even something whimsical that you both can laugh at.
  9. What topic(s) would you never joke about? This will help you get a good idea of someone’s sense of humor and their boundaries. Personally, I don’t joke about rape, gender, sexuality, or feminism, so anyone who finds these subjects funny raises a red flag for me.
  10. Are you spiritual or religious? A good way to get to know someone is by getting them to talk about their religious beliefs or lack of it. Is God a big part of their life? What kind of spirituality do they practice? How do they feel about people who don’t share their beliefs? Why don’t they believe in the existence of God?
  11. What are you most proud of? This will not only give you insight about the kind of life they’ve led, it will also get them to open about the things that are meaningful to them. Prompt them to be specific, no matter how small the accomplishment might be. The only important is that they found great joy in it.
  12. Your favorite book/song/TV series? The kind of books, movies, or songs that someone likes are a kind of window into who they are. It can reveal what subjects they find fascinating. You can also expand the field of inquiry to other things they like or enjoy doing or vice versa.
  13. What does a perfect life look like to you? I promise you that this question is going to help you uncover so much about a person. You might realize that they have a different idea of what counts as perfect and get important insight into their desires for the future.
  14. What are you most afraid of? Everyone is afraid of something, irrational or logical, so asking about their fears will help you get to know and understand someone. Pay attention to their explanation for why they consider whatever they say frightening, that’s where the juice lies.
  15. If you had the power, what would you change about the world? Given the power, the things I’d like to rid the world of are sexual violence and climate change. Whatever answer the person you ask gives will give you a deeper understanding of who they and how they move through the world.
A girl preoccupied with living her best life even when it's uncomfortable to do so. She spends a lot of time with her thoughts. She hopes you enjoy reading the results of those thoughts.