5 questions to ask a stranger.

Finding it hard to connect with new people through small talk I decided to compiled a list of questions that would help establish an open line of communication and a more lasting encounters. I’ll go through each question and explain why I choice it as one of the five. These questions will challenge and establish trust, honestly, and vulnerability; The three properties of healthy friendship. Along with the answers it is wise to be aware of how the person acts whilst asked and answering the quinary. Body language, vocal tone and eye contact are important to note as they are just as much a part of the words being released. Although I’ve rarely ever started a conversation with “Hello, what’s the single most important thing to you?” I can say I am not against this approach but personally find it more beneficial to ask these when it is known that there is ample time for the recipient to think on and answer at their own pace. I also find it appropriate if it’s a individualized encounter and there as been proper introductions between us. These two factors can give a sense of security and openness between the two participants. (Note: It may be healthy to acquire a pen and parchment to answer and reflect on these before going on to the “Whys”.)

  1. What is the single most important thing to you? (It doesn’t have to be a tangible thing).
  2. Give me some advice?
  3. Whats your story?
  4. Why do you choose to continue living?
  5. What do you think of me?


What is the single most important thing to you?

This inquiry embodies a few important qualities, the most transparent being a sense of interest in the others values and passions. Secondly in its nature the question is very personal but not invasive, allowing the speaker to become vulnerable well still feeling confident and comfortable, making them more receptive to later sensitive questions. Even those who are shy will find themselves happy to speak on something they believe holds value. Third, we gain insight as to what life style this stranger may live, what motivates them and at what stage of life they may be at. (Note: Found it important not to interrupt or speak until they have fully finished with their answers, giving them plenty of time to pause and think whilst keeping scrutiny attention. A good indication of there conclusion is when they say “What about you?” or “You said you have more questions?”.


Give me some advice?

This give the impression that you are open and interested in new ideas, showing your side of vulnerability as a feeling of equality settles into the conversation. If answered honestly it will reveal the thinkers mental state and current mind set. Did their answer fall more on the side of personal growth, mental health, environmental concern, community or family bases? Pulling from there answer you can understand some of their passions and interests along with a hint of morals. It may also reflect what they are going through at that moment in time. (Ex: “Never go to bed angry.” This could have a connection to a personal relationship or lose they may be dealing or have dealt with and could later be brought up to aid them in moral support.) Although most times the return will be one of humor such as “don’t eat the yellow snow” or ” look both ways before crossing the street” This is normal if the person is not familiar or accustom to being challenged with on spot questioning. Normally they’re answer will change once they ask for your thoughts on the subject. (Note: Again, it is helpful to inform them that there is no rush and they can always get back to you if they need more time to think).


Whats your story?

This will be the turning point in the conversation, opening the flood gates to trust and vulnerability. Along with getting a lot of information about the tellers attitude towards their live. You’ll be able to gather some thick view points, self perceptions and again what they might find important and interesting. (Note: I find that the more open I am when asked to speak on “my story” the more likely they are to release more intimate pieces of history.)


Why do you choose to continue living?

This can be off putting to some but can be cleared up by following it with “As in what fuels you?” A large portion of thought lead to this question and will be touched on in another post titled Happiness is “the goal?”. As bazaar as the question may seem, it is a choice and will help scratch the surface of there spiritual views if they possess any. How is this helpful to those who don’t entertain the thought of an afterlife? It’s not, but neither is it helpful to those of faith, the way the question is answered is that of importance. Listen carefully, is their answer one of optimism, indifference, mysticism, confusion, curiosity? Questions of life and death reveal ones attitude and feelings towards the value of existence.


What do you think of me?

At first glance this can be misconstrued as a way to feed ones ego but upon further observation it is a wonderful way to establish honesty and trust in a relationship, by showing you are open to criticism or compliments you’re allowing the other to express there first impression freely and a sense of safety is conceived. Although most will only give compliments and be impatient to hear how you’ll flatter them, This question hold the same value as asking someone to do a favor for you. If they are willing to do the favor (tell you there thoughts on you) they’re accepting your invitation of friendship and will feel comfortable in your presents.



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