In this article, I am going to suggest 50 personal, original, and slightly compromised questions that will help you 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? Or What is your favourite song?
In addition to helping you to create a fun and trustworthy 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 Why, Which, or How ), and they deal with emotional issues with which you can access the real passions and fears of the person you want to know better.
So, in a fun and original way, you will get conclusions about your personality without needing to be a psychologist. But if you have doubts, I will also help you interpret the answers they can give you.
One tip: not to turn your conversation into an interrogation, you also answer the same question you asked. This way, you will feel that he knows you more, and you will create a greater connection.
Curious questions to get to know a person better
1. What superpower would you like to have?
My favourite and the one I use the most. It will help you to know the wishes and fears of that person because, in reality, he will not be answering you about his hidden needs.
If she wants to become invisible, she’s probably a little shy. If you say you’d like to fly, will surely value freedom.
With your answer, think a bit and draw your own conclusions. Usually, the superpower you would choose is an extreme manifestation of the emotions that govern your life.
2. If you could only have a hobby, what would it be?
Asking for hobbies may seem typical, but it is essential 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 will know if that person is an athlete, detailed, 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 he answers that with a Hollywood actor, he may be more interested in fame and popularity.
4. Would you be able to forgive cheating if you knew that person really loves you?
Be careful with this question because it can evoke bad memories if you have suffered a similar experience or raise suspicions if you still don’t know yourself too much, so it is better to reserve it for when there’s more confidence.
While your answer doesn’t have to be what you’d really do in a situation with such an emotional burden, it will help you 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 the physical more than material possessions. But it is a trick 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 distributed at 50%. What would you choose?
6. What is the most magnificent madness you have committed in your life?
A classic but handy question to understand what level of emotions you want in your life. It will help you to know if a rebel spirit is hidden 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 favourite word?
People often have colours, movies, books, actors, songs, foods, and favourite places, but we have never stopped to think about what our favourite word is. It is paradoxical because what we use most in our lives are words.
This way, you may not get much information about the other person, but you will make them think for a while, and their response will give you clues about their lexical and cultural level.
By the way, my favourite word is a paradox. 🙂
This way, you may not get much information about the other person, but you will make them think for a while, and their response will give you clues about their lexical and cultural level.
8. If you knew you were going to die precisely within a year, how would you change the way you live?
Most people will reply that they would stop working and would be travelling, but it can also be an exciting approach to deduce how much your family or loved ones value (if you answer that you would try to spend as much time as possible with them). You will also understand what gives you the greatest pleasure in your free time, whether it’s eating, sleeping, or having sex.
9. If you were a pizza topping, what would you like to be?
In a sociological study on speed datings, curiously, this question was the best valued among all those that were asked. The reason? Quick dates can be quite dull, especially when you’re sick of asking what you do, where you live, etc. In these situations, the original questions make a difference and get people to relax to continue deepening.
It probably won’t help you get to know the other person, but surely you make her laugh and take the stress off the situation, making her feel more predisposed to answer more committed questions.
10. Would you prefer to go to the future or the past?
This approach will serve you mainly to deduce if you have historical and cultural concerns (if he tells you that he would travel to ancient Greece, for example), or if he prefers the novelty and excitement of a trip to an unknown future. It can also give you an idea of whether he deeply regrets something that has happened to him if he tells you 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 famous character would you like to be?
Here you can consider several options, such as actor, singer, scientist, politician, or athlete. If he tells you something like a rock star, it probably means he likes to be the centre of attention and needs social validation. If you answer that a famous investigator, it is perhaps an introverted, calm, and thoughtful person. You can draw your own conclusions!
12. How would you describe yourself in 3 adjectives?
A fundamental question that many people will not know how to answer or tell you generic things like fun, friendly, loyal, etc. Ask them to dig 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 prepared too because then he will ask you!
13. What is that you cannot bear in others?
The answer to this question is complex to interpret, but it can give you valuable information. According to Jung’s analytical psychology, what we hate most in others can be a fear buried in our unconscious, a reflection of ourselves that we don’t want to see. Therefore, if he tells you that he hates people who want to be the centre of attention, it may mean that he feels lonely and undervalued. In any case, watch with the interpretation.
14. If you wrote everything that has happened to you so far in a book, do you think people would want to read it?
This question stems 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 most considerable interest is in the differences that may arise in the subsequent conversation since it will plainly also confess your dreams and projects.
15. How’s your car’s trunk?
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 favourite saying?
The answer will give you a source of information to meet that person. Basically, you will understand what he values in life, his attitude towards her, and if he is optimistic or pessimistic. Beware of taking it literally because it often 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 this person is very determined, but perhaps he would like to be. When they tell me “better late than never,” I know that I am probably in front of someone who postpones everything.
17. How wrong do people who still don’t know you judge you?
An interesting question because the image we believe in the project does not have to be the one that others perceive. Your answer will help you understand what the characters that you least like associated with it (whether you have it or not) are and how you would like people in your social circle to see you.
18. Where would your ideal vacation be?
Another classic but useful question. It will help you to know what attitude towards life that person has. Someone who prefers a vacation lying in a hammock in the Caribbean will surely not be as active on weekends as someone who wants to get to know 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 of the lives of celebrities, we do not usually know in-depth, but that of our friends.
When you raise this, people will surely doubt it, but it is an excellent question to meet someone. You will discover what qualities he admires in people.
20. What was your favourite cartoon series?
This is wonderful because it evokes childhood memories and forgotten feelings. And if it turns out that you know the series and can talk about it for a while, I wish you an inspiring 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 the way you were raised?
Well, we get into a pretty committed and emotional question. The answer will depend in no small extent on the degree of trust that exists between you and your interlocutor, but in any case, it will cause it to open up and get to know you 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 enough.
22. If you could buy only one thing, whatever it was, what would you buy?
It will be useful to understand your priorities and dreams in life. If he replies that a mansion would be bought, he surely values stability and family life above all else. If he tells you to go around the world, it is probably an adventurous and free spirit.
23. What 3 qualities do you appreciate most in a person?
People usually answer logical things like honesty, loyalty, and sincerity, so you should ask them not to talk to you about values but about attitudes or behaviours. “That my partner tells me his problems when they happen to him” or “that if a friend thinks I have screwed up, he tells me,” they are examples of behaviour.
This question will help you to intuit the kind of social and sentimental relationships that a person has had.
24. If you could learn to do something new, what would you choose?
Another excellent question to get to know someone better without compromising. It will guide you about your daily needs and desires, and about what embarrasses you a little and wants to correct.
25. Who do you think would win in a fight? You or your best friend?
Although it may seem like a comic question (which is), it will give you an idea of how powerful or influential you feel with the people around you. You can modify the subject 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 an excellent investment of time. Therefore the person who reads it has to be willing to start it and convinced to finish it. In this way, you will get much more information about what he is passionate about if you ask him about his latest movie or play.
27. If you could be an animal, what would you be?
Depending on the animal that tells you, you will know what characteristics it appreciates and how it sees itself: strong, skilful, feline, sensual, free, lethal, harmonic, 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 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 are usually more short-term oriented and more thoughtful ones better anticipate 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 be able to understand someone’s personality better because almost everyone remembers our childhood with friends or grandparents with love, it will help you to create a much more emotional state in your interlocutor that will help you to know him in greater depth from the conversation you have.
30. What part of your body do you like most?
You could also ask the least, but we will leave that for when you have more confidence. This question is easy to interpret because it will tell you the physical attribute of the one you are most proud of, the one who has been most complimented, or of which you would like to be able to presume because you believe that the opposite sex is the most fixed one.
If the situation occurs, make a compliment on that particular part. It will do twice as well.
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 you would like to be a person.
Asking someone to define himself with a phrase, if he has never done so, is very difficult. Ask him and tell him that it is not necessary to answer you at the moment that he can give you the answer the next day you saw yourself. The slogan must be short, unique, and realistic. And it is also a self-knowledge exercise that will probably thank you for having introduced.
32. What is the best and worst quality of your gender and the opposite?
If you want to know what you think of 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 straightforward way to understand what kind of life you would like to lead. A quiet country life? Or a life full of stimuli in a big city? Do you prefer cold? Or do you feel more comfortable in warm environments? Feel free to customize the question as much as you want, either by 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 someone in depth. What motivates you the most? The money? Social recognition? The family? The appreciation of your friends? Solidarity? In this way, you can have a distinct idea about what moves that person when making decisions.
It will also give you information about what things you can desire in others, since when someone wants fame and recognition, they may not be able to bear others getting it.
35. What is the weirdest item in your room?
More than to find out about his personality, this question will be useful for you to tell you about an exotic trip or anecdote that has happened to him a long time ago. Usually, our most curious possessions come from travel, gifts from previous relationships, or rocambolesque situations. Take advantage of it to learn a little more about your life.
36. Travel all over the world without being able to return to your country, or never leave it?
No doubt, a difficult question to answer. The idea of travelling around the world is attractive, but giving up not stepping on the place where he was born is a great dilemma. If he tells you that he would prefer to travel the world, he surely has an adventurous soul and does not like being tied to anything or anyone else.
37. What was the last lie you said?
This should be considered in a fun and light way since 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 you are a sincere person. If you answer a vast lie, it may be less difficult to hide the truth.
38. Do you prefer a life full of sex but eating fatal, or a life without sex whole of sumptuous 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 immense pleasures, so if you don’t judge her, whatever your answer is. Although if he tells you that he prefers sex, he really values it as an essential part of his life!
39. Do you think you know yourself well?
When someone answers yes to this question, he usually indicates that he is a person with enough confidence and self-confidence. If, on the contrary, he thinks he is not well known, he may have some self-esteem deficit, although there are always exceptions.
40. What kind of sense of humour do you have?
Humour is one of the aspects that best define a person’s personality. Therefore, knowing her style (ironic, black, absurd, direct, etc.) is essential to understand her way of thinking better and seeing life.
41. If you could have any job in the world, which one would you choose?
A priori with this question, you can understand a little better his childhood dreams and what kind of people or professionals he admires. Also, it is usually a good idea to relate the profession to their aspirations and desires because they are typically linked.
If, for example, he tells you that he would like to be a doctor, he probably feels fulfilled helping people. If he tells you that he would like to be a pilot, he surely values freedom and the possibility of travelling the world. Dare to interpret your answer yourself 😉
42. What is your favourite conversation topic?
It seems incredible how many times we go blank without knowing what to say, looking for conversation topics that may interest the other person. And why not ask directly what is your favourite item of conversation?
In this way, you will know with certainty about 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 thoughtful, among other things.
43. What is your biggest fear in this life?
This question is complex and requires some confidence before asking it because it is a bit personal, but it will also give you a lot of information about your personality. Perhaps you can glimpse some of his phobias or obsessions (although he will surely tell you that they are not so important), and you will be able to see if he gives more weight to material fears, such as spiders or running out of money, or to more abstract concerns, 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 usually treat our loved ones VERY similarly. Therefore, the way someone treats their parents can predict how they will relate to their new partner as soon as there is greater trust.
Although maybe I can lie to you in the answer, if you have any romantic intentions with that person, I advise you to observe how they treat their family environment. It will give you many clues to the future that is coming.
45. What would be your ideal profession?
It will allow you to deepen your childhood dreams since trade is something in which people place high hopes. Almost no one dreams of being a pizza delivery man or a call centre telephone operator, no matter how much these professions require a great gift from people.
It will also help you to know some of its values, such as helping others if they tell you that they would like to be a doctor, the adventure if they answer you as a fighter pilot or even money.
46. What is the most beautiful thing you have done for love?
Another one of those committed questions that will give you a lot of information about the way you want.
You will quickly discover if he is a romantic person, or if on the contrary, he is more pragmatic and cold. The latter does not have to mean that it is not very passionate, merely that it does not require too many demonstrations to love and feel too much.
47. Do you prefer to read fiction or nonfiction?
Ah, one of my favourite questions because it quickly lets you know if that person is very logical and a perfectionist (in case he prefers to read nonfiction books) or dreamer and nonconformist (if he likes fiction books more).
The next question is, of course, what is your favourite book 😉
48. What do you like best, dogs or cats?
Although the answer to this question may depend a lot on the personal tastes and experiences of each one with that particular animal, it is true that those people who do not need so much appreciation and value freedom more often prefer cats.
On the other hand, who values loyalty and affection probably feels a predilection for dogs, although there are also many behavioural differences between breeds (a Doberman is not the same as a farmer, for example).
49. If you could stay a lifetime of the same age, what would it be?
We all have had times of great joy in our lives. Great and joyful 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 the responsibilities.
If he tells you that he would stay a lifetime with 15 years, he probably doesn’t like to think about significant commitments.
50. What is the best question that you have been asked, or could you be asked?
And finally, a question that will make you reflect for a while. Asking what the best item that you have been asked or could ask you will give you a lot of information about what you are most proud of or what you most want is.
For example, if he answers that it was “How far would you be willing to go for your loved ones?” Is that probably one of his central values is the sacrifice for the family.
In any case, do not let him leave without answering this question.
Do you have any questions that worked exceptionally well to get 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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