Curiosities

50 Interesting Questions to Know Someone Better

In this article, I am going to propose 50 personal, original and slightly committed questions that will help you to know more about the character and preferences of the person you want to meet without falling into the typical ones. What would you take to a desert island? What is your favorite song?

Besides that, they will help you create a fun and trusting climate, you can also apply them in your usual social relationships to start much more interesting conversations, so do not hesitate to use them with your boyfriend or girlfriend, friends and acquaintances.

The questions you will find in this article are open questions (they begin with What, What or How ) and deal with emotional issues with which you can access the true passions and fears of the person you want to know better.

Thus, in a fun and original way, you will get conclusions about your personality without having to be a psychologist. But in case you have doubts, I will also help you interpret the answers they can give you.

A tip: in order not to convert your conversation into an interrogation, you also answer the same question that you have asked. In this way, you will feel that you know more and you will create more connection.

Curious questions to know a person better

1. What superpower would you have?

My favorite and the one I use the most. It will help you to know the desires and fears of that person because in reality, he will be answering you about his hidden needs.

If she answers that she wants to become invisible, she is probably a bit shy. If he says he would like to fly, he will surely value freedom. If I wanted to be able to read my mind, it is that I may have been betrayed in the past and now distrust people.

With your answer, think a bit and draw your own conclusions. Normally the superpower you would choose is an extreme manifestation of the emotions that govern your life.

2. If you could only have one hobby, what would it be?

Asking about hobbies may seem typical, but it is imperative to meet someone. If you want to avoid answers like “read, go to the movies and meet friends” I recommend that you ask me to tell you only one. In this way, you can know if that person is an athlete, retailer, competitive, sociable or passionate.

3. If you could go to dinner with a historical character, who would you go with?

An excellent question to understand what concerns that person has. If he tells you that he would go with Gandhi, he surely has humanitarian and social concerns. If you answer that with a Hollywood actor, you may be more interested in fame and popularity.

4. Would you be able to forgive an infidelity if you knew that person really loves you?

Beware of this question because it can evoke bad memories if you have suffered a similar experience or raise suspicions if you still do not know too much, so it is best to reserve it for when there is greater confidence.

Although your answer does not have to be what you would really do in a situation with such emotional burden, it will help you to assess how much commitment you give to a relationship.

5. Between being the most attractive person in the world but also the poorest, or the richest but ugliest, what would you choose?

One of quite curious. It will give you clues about whether you value more physical than material possessions. But it is a tricky question because wealth and beauty are both superficial values and there is no one better than the other.

All the women to whom I have asked this question have responded that they prefer beauty, while among men the thing is shared at 50%. What would you choose?

6. What is the greatest madness you have ever committed in your life?

A classic but tremendously useful question to understand what level of emotions you want in your life. It will help you to understand if a rebellious spirit hides behind its serious and formal aspect, or if on the contrary, it prefers stability and few surprises. You can probably also get a good idea of what kind of childhood he had.

7. What is your favorite word?

People often have colors, movies, books, actors, songs, foods and favorite places, but we have never stopped to think about what our favorite word is. It is paradoxical because what we use the most in our lives are words.

In this way, you may not get much information about the other person, but you will think for a while and their response will give you clues about their lexical and cultural level.

By the way, my favorite word is paradox 🙂

8. If you knew that you were going to die exactly within a year, how would you change your way of living?

Most people will respond that you would stop working and travel, but it can also be a very interesting approach to deduce how much you value your family or loved ones (if you answer that I would try to spend as much time as possible with them). You will also understand what it is that gives you the most pleasure in your free time, whether it’s eating, sleeping or having sex.

9. If you were a pizza topping, which would you like to be?

In a sociological study on speed datings, curiously this question was the best valued among all those that were made. The reason? Quick appointments can be quite boring, especially when you’re tired of asking what you do, where you live, etc. In those situations, the original questions make a difference and get people to relax to continue deepening.

Probably it will not help you to know the other person, but surely you make her laugh and remove tension from the situation, making her feel more predisposed to answer more committed questions.

10. Would you rather travel to the future or to the past?

This approach will serve you mainly to deduce if you have historical and cultural concerns (if it tells you that you would travel to ancient Greece, for example), or if you prefer the novelty and excitement of a trip to an unknown future. It can also give you the idea of whether he deeply regrets something that has happened to him if he tells you that he would travel back to change something in his life.

By the way, I would travel to the future. And you?

11. What kind of celebrity would you like to be?

Here you can consider several options, as an actor, singer, scientist, politician or athlete. If he says something like a rock star, it probably means that he likes to be the center of attention and needs social validation. If you answer that a famous researcher, it is probably an introverted, calm and reflective person. You can draw your own conclusions!

12. How would you describe yourself in 3 adjectives?

A very powerful question that many people will not know how to answer or they will tell you generic things like fun, friendly, loyal, etc. Ask them to delve deeper, to be more specific. That will give you information not only about how they are, but how they would like to be. And have your answers ready too because later he will ask you!

13. What is it that you can not stand in others?

The answer to this question is complex to interpret but it can give you very valuable information. According to Jung’s analytical psychologywhat we hate most in others may be a fear buried in our unconscious, a reflection of ourselves that we do not want to see. That’s why, if she tells you that she hates people who want to be the center of attention, it may mean that she feels alone and underappreciated. In any case, watch over the interpretation.

14. If you wrote everything that has happened to you so far in a book, do you think that people would want to read it?

This question comes from the beautiful motivational phrase “Make your life a book worth reading”. It will give you a lot of information about whether that person is comfortable with himself, or if, on the contrary, he is dissatisfied and feels tied to his comfort zone.

But the greatest interest is in the nuances that may arise in the subsequent conversation, as it surely confesses your dreams and projects.

15. How do you have the trunk of the car?

I firmly believe that the trunk of a person’s car is a reflection of their internal mental order. And so far it has not failed me. Messy trunk = chaotic person 😉

16. What is your favorite saying?

The answer will give you a source of information to know that person. Basically you will understand what you value in life, your attitude towards it, and whether you are optimistic or pessimistic. Beware of taking it literally because many times it hides the ideal of what the person would want.

“Do not leave for tomorrow what you can do today” does not have to mean that that person is very determined, but maybe he would like to be. When they say to me “better late than never” I know that I’m probably in front of someone who postpones everything.

17. In what wrong way do you judge people who still do not know you?

A very interesting question because the image we think we project does not have to be what others perceive. Your answer will help you understand which feature you least like to associate with her (whether she has it or not) and how she would like to be seen by people in her social circle.

18. Where would your ideal vacation be?

Another classic but useful question. It will help you to know what attitude that person has in front of life. Someone who prefers a vacation lying in a hammock in the Caribbean will surely not be as active on weekends as anyone who wants to go and meet exotic cultures.

19. If you had to become one of your friends, who would it be and why?

The best variant of the classic “if you could be a famous character, which one would you choose?” Because the lives of celebrities do not usually know in depth, but that of our friends.

When you pose this surely people will doubt, but it is a good question to know someone. You will discover what qualities you admire in people.

20. What was your favorite cartoon series?

This is wonderful because it evokes memories of childhood and forgotten sensations. And if it turns out that you know the series and you can chat about it for a while, I predict a very exciting talk. By itself, it does not give information, but you will get it as a result of the emotional conversation that arises.

21. What would you like to change in the way you were raised?

Well, we entered into a very committed and emotional question. The answer will depend in large part on the degree of trust between you and your interlocutor, but in any case, it will cause you to open up and get to know yourself more, which is very positive. Here you can get an idea of what he would have liked to have during his childhood, either because he envies him in his friends or because he made him suffer a lot.

22. If you could buy just one thing, whatever it was, what would you buy?

It will be useful to understand your priorities and dreams in life. If he answers that he would buy a mansion, he surely values stability and family life above all else. If he tells you that around the world, he is probably an adventurous and free spirit.

23. What 3 qualities do you appreciate most in a person?

People usually respond to logical things like honesty, loyalty, and sincerity, so you should ask them not to talk about values, but about attitudes or behaviors“That my partner tell me their problems when they happen” or “if a friend thinks I screwed up, tell me” are examples of behavior.

This question will help you to intuit the type of social and sentimental relationships that person has had.

24. If you could learn to do something new, what would you choose?

Another very good question to know someone better without putting her in a compromise. It will guide you to your most daily needs and desires, and about what you are ashamed of a little and want to correct.

25. Who do you think would win in a fight? You or your best friend?

Although it may seem a comical question (which it is) will give you an idea of how powerful or powerful you feel in relation to the people around you. You can modify the question as you wish, replacing your friend, your brother, your boss or even yourself. Surely it also helps you to start a fun conversation!

26. What is the last book you have read?

A book is a great investment of time. Therefore the person who reads it has to be willing to start it and convinced to finish it. This way you will get much more information about what you are passionate about than if you asked about his latest film or play.

27. If you could be an animal, what would you be?

According to the animal that tells you, you will be able to know what characteristics you appreciate and how you see yourself: strong, skillful, feline sensual, free, lethal, harmonious, etc. Maybe it surprises you!

28. Are you one of those who would sacrifice a person’s life to save a hundred?

With this question, you will be able to know if for the other person the end justifies the means. It will also give you clues as to whether it is more rational or emotional, because emotional people tend to be more oriented to the short term and the more reflective ones foresee better the long-term consequences (saving the lives of more people, in this case).

29. What is the best memory of your childhood?

Although this question is not very useful to better understand someone’s personality because almost all of us remember fondly our childhood with friends or grandparents, it will help you to create a much more emotional state in your interlocutor that will help you to know it in greater depth from the conversation you keep.

30. What is the part of your body that you like the most?

You could also ask the least, but we’ll leave it for when you have more confidence. This question is easy to interpret because it will tell you the physical attribute of the person who feels most proud, the person who has been complimented the most, or who would like to be able to presume because he believes that the opposite sex is the one that is mostly fixed.

If the situation occurs, give him a compliment about that particular part. It will be twice as good.

31. What would be your slogan?

This is quite complicated, but it is the question that will give you more information about what it is like and how a person would like to be.

Asking someone to define himself with a phrase, if he has never done so, is very difficult. Ask him and tell him that he does not need to answer you at the moment, that he can give you the answer the next day you saw him. The slogan should be short, unique and realistic. And it is also an exercise in self-knowledge that will probably thank you for proposing it.

32. What is the best and worst quality of your gender and the opposite?

If you want to know what you think about men and women in general, ask this question.

The trick is that many times the opinions we have about the opposite sex are based on our own experience, so it will give you information about the type of relationships you have had and how they have affected you .

33. Where in the world would you like to live?

It is a very simple way to understand what kind of life you would like to take . A quiet life in the countryside? Or a life full of stimuli in a big city? Do you prefer the cold? Or do you feel more comfortable in warm environments? Feel free to customize the question as much as you want, either asking for a specific country or city.

34. What motivation moves your life?

A very philosophical question, but perhaps one of the most important in this list to know in depth someone . What motivates you the most? The money? The social recognition? The family? The appreciation of your friends? The Solidarity? In this way you can have a very clear idea about what moves that person when making decisions.

It will also give you information on what things you can envy in others, because when someone wants fame and recognition may not be able to endure that others get it.

35. What is the rarest object in your room?

More than to find out about your personality, this question will be useful for you to tell you about an exotic trip or anecdote that has happened to you long ago. Normally our most curious possessions come from trips, gifts from previous relationships or bizarre situations. Take advantage of it to learn a little more about his life .

36. Traveling around the world without being able to return to your country, or never leave it?

Undoubtedly a difficult question to answer. The idea of traveling around the world is attractive, but giving up on not going back to where you were born is a big dilemma. If he tells you that he would rather travel the world, he surely has an adventurous soul and does not like to be tied to anything or anyone .

37. What was the last lie you said?

This should be considered in a fun and light, as there are people who feel uncomfortable confessing this kind of thing. Anyway, your answer can be very revealing: if the deception that reveals you is inconsequential, surely be a very honest person. If you answer a huge lie, it may cost you less to hide the truth.

38. Do you prefer a life full of sex but eating fatal, or a life without sex full of delicious delicacies?

Here is the question that will allow you to understand how much you value sexual activity in a fun and original way. Both are huge pleasures, so if you do not judge it whatever your response. Even if he tells you that he prefers sex, he really values it as a very important part of his life!

39. Do you think you know yourself well?

When someone answers yes to this question, they usually indicate that they are a person with enough confidence and self-confidence . If, on the other hand, you think you do not know yourself well, you may have some self-esteem deficit, although there are always exceptions.

40. What kind of sense of humor do you have?

Humor is one of the aspects that best defines a person’s personality . Therefore knowing your style (ironic, black, absurd, direct, etc.) is fundamental to better connect with it and understand your way of thinking and seeing life.

41. If you could have any trade in the world, which one would you choose?

A priori with this question you can understand a little better your childhood dreams and what kind of people or professionals you admire. In addition it is usually a good idea to relate the profession with your aspirations and desires because they are usually linked.

If, for example, she tells you that she would like to be a doctor, she probably feels fulfilled helping people. If he tells you that he wants to be a pilot, he surely values freedom and the possibility of traveling around the world. Dare to interpret your answer yourself 😉

42. What is your favorite conversation topic?

It seems incredible how many times we go blank without knowing what to say, looking for conversation topics that might interest the other person. And why not ask him directly what is his favorite topic of conversation?

In this way you will know with certainty what topics he likes to talk about and what concerns he has , whether he is a rational or emotional person, modern or traditional and curious or reflective, among other things.

43. What is your greatest fear in this life?

This question is complex and requires some confidence before doing it because it is a bit personal, but it will also give you a lot of information about your personality. Maybe you can glimpse some of his phobias or obsessions (although he will surely tell you that they are not so important), and you can see if he gives more weight to material fears, such as spiders or running out of money, or to more abstract fears, such as death or not find its meaning in life.

44. What kind of relationship do you have with your parents?

The answer to this question is transcendental. People tend to treat our loved ones in a VERY similar way . Therefore, the way someone treats their parents can predict how they will relate to their new partner as soon as there is more confidence.

Although I may be able to lie to you in the answer, if you have some romantic intention with that person I advise you to observe how he treats his family environment. It will give you many clues about the future that is to come.

45. What would be your ideal profession?

It will allow you to deepen your childhood dreams , since the job is something that people place high hopes on. Almost nobody dreams of being a pizza delivery man or call center operator, no matter how much these professions require a great gift of people.

It will also help you to know some of its values, like helping others if it tells you that you would like to be a doctor, the adventure if you answer that fighter pilot, or even the money.

46. What is the most beautiful thing you have done for love?

Another of those questions committed that will give you a lot of information about their way of wanting .

You will quickly discover if it is a romantic person, or if on the contrary it is more pragmatic and cold. The latter does not have to mean that it is not passionate, simply that it does not require too many demonstrations to love and feel too much.

47. Do you prefer to read fiction or nonfiction?

Oh, one of my favorite questions because it quickly lets you know if that person is very logical and perfectionist (in case you prefer to read non-fiction books) or dreamer and non-conformist (if you like fiction books more).

The next question is, of course, what is your favorite book 😉

48. What do you like best, dogs or cats?

Although the answer to this question may depend a lot on personal tastes and the experiences of each one with that animal, in particular, it is true that those people who do not need so much appreciation and value more freedom tend to prefer cats.

On the other hand, those who value loyalty and affection probably have a predilection for dogs, although there are also many differences in behavior between races (a Doberman is not the same as a farmer, for example).

49. If you could stay your whole life with the same age, what would it be?

We have all had times of great joy in our lives. Intense and happy times, where we have enjoyed more than ever. That is why your answer will give you two types of information: when were the happiest moments of your life and to what extent you feel comfortable with responsibilities.

If he tells you that he would stay with his life for 15 years, he probably does not like to think about big commitments.

50. What is the best question that they have asked you or could they ask you?

And finally, a question that will make you reflect for a while. Asking what is the best question you have been asked or could be asked will give you a lot of information about what you are most proud of or what you most want.

For example, if you answered that it was “How far would you be willing to go for your loved ones?” Is that probably one of its main values is the sacrifice for the family.

In any case, do not let it go without answering this question.

Do you have a question that worked especially well for you to know someone better? Leave it in the comments section because if it is useful and original I will include it in the article itself 🙂


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Dipsita Thakkar

I am passionate about communication, studying human behavior and getting lost anywhere. I help you overcome your fears and transform your social life with the science of social skills.

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