Meaningful questions to ask someone you want to get to know?

What are some examples of good, introspective questions to ask someone you want to get to know on a deeper, personal level? Instead of superficial questions like “What are your hobbies? What’s your favorite color?” Etc.

If you are on a date perhaps, what are some thoughtful questions to ask that will give more insight to a person’s character?
Should the questions be about their childhood/past? Or plans and aspirations for the future?
Thanks for the help in advance!

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Most Helpful Guy

  • If you want to make a deep connection with someone, nothing gets to their heart more than someone who wants to understand them on a more, personal level where most people would have a hard time responding or asking such questions. What you mentioned about their childhood/future aspirations is a great place to start! Here's a few I can think of:

    "What do you think of our world today? Do you like it or hate it?
    (To better understand their point of view on the world which can relate to something in their personal life such as depression and social behavior.)

    "What qualities do look for in a friend?"
    (To find out more about how they want to be treated, which can help you understand what kind of friendship will make them the happiest!)

    "I'm curious how your current relationship is going? Do you like them?" or "If you're looking to be in a relationship, what kind of person do you want?"
    (This helps understand their emotions needs and flaws that they find not only within themselves but others as well.)

    "Have you ever felt like you are alone at times?"
    (To being out their emotions of finding out what their home life is like, alongside with current friendships and relationships they are in.)

    You can get really creative with your questions in where you can find out multiple sources of information at the same time! There's always those typical casual questions like "What's your favorite..." or "Where in the world do you want to travel?" but they are nothing more then mere facts; that it's not actually bonding with them on a more personal note. Hope you can find some of these to be inspiring for friendships you may have/are looking forward to!

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    • I really like these, thank you. I like that you managed to combine several concepts into one question, especially the “what do you think of the world today?” one. That leaves a lot of room for interpretation, which will also give insight into what someone prioritizes or thinks a lot about. It could lead to a political, religious, environmental, or a philosophical discussion depending on the person.

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    • It’s all good, no worries lol, I understand what you meant. That’s a really good point, too, about starting with a general question rather than making it awkward by being too direct. It allows the other person to open up more about themselves in a way that they’re comfortable doing while also gaining intel on them haha :D

    • Thank you for understanding X3 Maybe that's a reason why so many people go with general questions, to avoid accidentally offending someone or not make too much of a connection with them. It's playing it safe while taking no risks. That's pretty much the rule of thumb! Kinda makes you feel like a spy who discreetly gains intel without breaking into a place in an obvious way like shattering a window or is seen in plain sight!

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What Girls & Guys Said

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  • I guess you're from western society. In this society we have a patern of first asking mundane questions then progressively slide towards more intimate topics.
    You can read the 36 questions to fall in love to have an idea of that pattern and for some interesting questions :
    mobile.nytimes.com/.../...ig-wedding-or-small.html

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  • Hey hey hey, "what's your favorite color?" Isn't a superficial question.

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  • Maybe some plitical and spiritual ones. Sex history. Overall reason why they want tl be with you. And if they like lemon ice cream

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  • Asking "why" questions seem to open up dialog into much deeper/introspective areas than most yes or no type questions. Why do you like that song? Why did you hate going to xyz when you were younger? Just be prepared to find the person stumped, or hesitant. They may not be that deep a person (yet) or they may be but haven't considered exactly what you're asking.

    Another gauge for who the person is beneath the surface is to open a dialog like this, then allow a space for them to ask things about you. If they naturally ask "why" questions back (even the same questions, although hopefully not only) that is very telling that they care, they want to know who you are really also. If you have to ask them to ask you questions or find yourself offering up an answer to an unasked question too many times they are likely dead weight and aren't looking for depth of character. Good luck

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  • Dont ask them what they like. Ask them what they dont like.

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  • What's next for you? How do you see yourself at 30? 40? What's on your bucket list of things to do?

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  • Ask why, if you ask questions with straightforward answers, follow up with, why?

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  • "What's your opinion on objective morality?"

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  • ask them how to say caramel?

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  • Yess

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