357 Best Questions To Ask To Get To Know Them Better

It's an ill-kept secret that, the way to get to know people better, is to ask them better questions. Since we're all chatting to people a great deal of the time, you might as well do it right.

But there's more to the art of asking than simply stating your desires–you can also ask better questions, and therein lies true mastery. When you ask good questions, you not only sound more intelligent and thoughtful in the eyes of others, but you also get more out of everything from conversations to interviews and negotiations.

In this article we'll show examples of great questions that will make your life easier–in just about every single context imaginable.

So grab a cup of coffee, put your feet up, and learn how to ask great questions. Before we get into our exhaustive list we are going to look at the 6 most common question types and what they can be used for:

1. Quick Questions

Quick questions can be used to kick-start a conversation, guide it to the right place or speed things up when there's not much time–such as in meetings or job interviews. They also offer a way to think aloud and tap into your unconscious creative processes. Here are some of the best:

"What would you do in my shoes, what would you do if you were me?"

"How did this come about? What makes this a problem now?"

"If I could just get X, Y and Z, how much time do I save a week? A month? Year?"

"If I could just get your top three tips or tools for x, y and z – what would they be?" (at the end of an article or video)

"If you had one rule to live by, what would it be and why? Or if you had one piece of advice to give me today, what would it be and why?" (ask people in their fields)

2. Brainstorming Questions

Getting good ideas out of your head is a bit like getting stubborn children out of the house: you need a checklist. Brainstorming questions are ways to force your mind to make connections between facts and ideas, sparking new insights and discoveries. Here are some of our favorite:

"If you could go back in time and tell yourself something when you were younger, what would it be?" (or ask that person in your head)

"What do I need to know to make this work?" (from business meetings or job interviews)

"What if X happened and Y happened? How would the world look then?" (ideal for sci-fi writers)

3. Discussion Questions

Discussion questions are for improving the quality of conversation by asking people to delve more deeply into topics, and to make connections they may have missed. They're also great at guiding a class discussion or meeting. Here are some of our favorites:

"What would have happened if we hadn't done that?" (from business meetings)

"What action do you think you would have taken in this situation?" (from phone interviews)

"If you had a time machine, what would you change about your past and how would it affect your life?" (best for history and sci-fi buffs)

4. Adjective/Noun Questions

These sorts of questions help refine information. They're especially useful in interviews, where it's often easy to select the wrong job for someone (and they're great at identifying candidates in a group). Use them to get to the heart of a topic or situation.

"What are you most worried about?"

"What would you do if you were me?"

"How does x make y different from z? Why is that good or bad? What other factors are involved?" (from job interviews)

5. Question Throw-Aways and Endings

You can even use questions as throw-aways at the end of sentences, or questions for their own sake–in conversation and in writing. They can be used to create interesting loops or drills in articles, books and more.

"What are the three best things about this?" (from business meetings)

"How would you use x in this situation?" (from phone interviews)

"Why is x important/dangerous/valuable/etc.?" (from job interviews)

6. Transitions Questions

Transitions are ways to help you move from one part of a conversation to another, or from one stage of an interview to the next. They're especially useful because they can also be used to answer your own questions as well as those you have posed.

"Who is responsible for x?"

"How do you think y happened in this situation?" or "How would you explain what happened to me in x?" (from phone interviews)

"What's important about this part of the process?" (from business meetings).

So those are the 6 most common question types, and here below is our list of great questions to ask to get to know someone better. If you would like an exercise to do, try classifying each of the questions into one of the 6 categories above.

Where is your favorite holiday destination?

This is a great question to see how a person likes to spend their free time. Are they the adventurous type who goes mountain climbing in Nepal or the relaxed type who enjoys spending time sunbathing at the beach? It will also allow the other person to speak to you about a happy time and they will enjoy telling you about it.

Can you tell me one thing about yourself that I already don't know?

By asking the other person to open up and show off their personality you offer them the chance to tell you something important about themselves. A question that gets the other person thinking and enables you to learn something they might not always share may allow you to deepen your relationship with that person.

Where do you like to go for a drink after work?

If the person you are talking to doesn't have too many hobbies or interests this is a good question to ask. It allows you to get a glimpse into their social life and show them that you're interested in what they have to say.

Do you have any pets?

This is a good question usually because everyone has a nice story about their pets, and it's an important question to ask because most people love pets. Pets are a great way to get to know someone outside of their work or school and will give you an insight into their personality.

If you could live anywhere in the world where would it be?

This is a question that shows the other person that you're interested in where they are from. It's a great question to ask if you find that you've never been to their hometown and you're curious about the place they grew up.

Are you planning on going to college?

This is a question that can tell you a lot about the other person. Not everyone is interested in getting a degree, but it's a good idea to ask them about their future goals. If they say that they aren't going to college you can suggest some alternatives and ask if they've thought about those options.

What's the weirdest thing that has happened to you recently?

This is a silly question because if you ask it you already know the answer to it. You ask the question because you're interested in what they have to say. It's a great way to get to know someone because it shows you're interested in them and what they have to say.

What's your favorite thing about your job?

This is a great question to ask someone who works in a job that you have a hard time understanding. It allows you to get a peek into what an office job or a job in the service industry is like and can get the person talking about something they enjoy.

If you could live anywhere in the world where would it be?

This is a question that shows the other person that you're interested in where they are from. It's a great question to ask if you find that you've never been to their hometown and you're curious about the place they grew up.

What's your favorite restaurant?

This is a question that will give you an idea of what kind of person the other person is. Do they like to spend lots of money to go to a fancy restaurant or do they like to chill out in a local diner? It's a great way to learn more about the person you're talking to.

What's your favorite board game?

There's no better way to get to know a person than to play a board game with them. You'll get a chance to ask more questions and see how they react to different situations. You'll also get a chance to see how they act when they're in a competitive situation.

What's your favorite thing to do at the weekend?

This is a great question to ask anyone, particularly if they're not your friend. You may find that the only thing they do is work and if you ask them this question you'll be able to get them out of the house. You can suggest going for a walk or playing a sport and you'll get to know them better outside of an office setting.

If you could have dinner with anyone who would it be?

Everyone has a celebrity or someone who they would like to have dinner with. This is a great question to ask a person because it shows them that you're interested in who they are and it gives you the chance to talk about someone you both admire.

What's your favorite food?

Everybody has their favorite food and this is a great question to ask someone if you want to get to know them better. It's a question that gets the person thinking about their favorite food and can be a good conversation starter.

What's your favorite TV show?

Everyone has a favorite TV show and it's a great way to get to know someone. It's also a good way to see what kind of person they are if they enjoy watching a silly comedy or something thoughtful and serious.

What's the worst job you've ever had?

Everyone has had a terrible job and if you ask this question you'll get to hear all about it. It's not the kind of question that you're likely to ask someone you see on a regular basis, but it's a great question to ask someone you've just met.

What do you do in your free time?

If you're trying to get to know someone this is a great question because it gives you an idea of what their interests are. It's not a question that everyone is going to be comfortable answering, but you can suggest a way to make it easier to talk about.

Are you planning on having kids?

This is a question that can give you insight into a person's personality. There's no right answer when it comes to kids and you should never assume that someone wants them or doesn't want them. It's a great question to ask if you want to get to know someone better. It can also give you the chance to talk about how you feel about kids.

What's your favorite piece of clothing?

This is a fun question to ask someone because you'll get to know a little bit about their personality. It's a simple question that you can ask someone you've known for a while or someone you've just met.

What's your favorite TV show?

Everyone has a favorite TV show and it's a great way to get to know someone. It's also a good way to see what kind of person they are if they enjoy watching a silly comedy or something thoughtful and serious.

What's the last book you read?

This is a great question to ask someone if you want to see what kind of person they are. It's also a good way to start a conversation and find out what they like to read.

What's your favorite movie?

Everyone has a favorite movie and this is a great way to get to know someone. It can also be a fun question to ask someone you've just met because you can talk about the movie and see if you have similar tastes in movies.

What was your favorite subject in school?

Everyone has a favorite subject and this is a good question to ask someone if you want to get to know them better. It's a simple question that you can ask someone you've known for a while or someone you've just met.

What's the last book you read?

This is a great question to ask someone if you want to see what kind of person they are. It's also a good way to start a conversation and find out what they like to read.

What's your favorite holiday destination?

This is a great question to see how a person likes to spend their free time. Are they the adventurous type who goes mountain climbing in Nepal or the relaxed type who enjoys spending time sunbathing at the beach? It will also allow the other person to speak to you about a happy time and they will enjoy telling you about it.

What's your favorite museum?

Everyone has a favorite museum and it's a fun way to get to know someone. If you're going to a museum with them you can talk about the upcoming exhibits and what kinds of things they like to see.

Do you like to cook?

This is a question that is going to give you a lot of insight into a person's personality. People who like to cook are responsible and organized and those who don't like to cook are usually the opposite. It's a fun question to ask someone and you can talk about the best meal you've ever cooked and the worst meal you've ever cooked.

Have you ever had a crush on someone?

If the person you are talking to has fallen in love with someone, then this question is important. Even if they haven't, it's nice to hear how they would have felt about it if they had found the right person at the right time! It will help them feel relaxed and comfortable with you, because of this question.

What's your favorite movie?

A question like this shows that you're interested in who the other person is as a person instead of what they do for a living or what they're doing this weekend. It avoids small talk about what is going on at work and allows them to share something about their personality and who doesn't like a good movie?!

Are you a morning person or a night person?

This is another question that tells a lot about the other person's personality without really telling you anything. Your friend could say that they prefer to sleep past noon, but still be productive and happy in the morning. It also allows you to see how a person likes to spend their mornings and if they're into the same things as you.

What's your favorite type of music?

Everyone has their own musical preferences and musical tastes are an important part of a persons life because it is essentially what makes them who they are. Music unites people and helps you understand the other person better. Everyone will have a different answer to this question too, which shows that you're actually interested in who they are as a person rather than what they do for a living.

Are you an optimist or a pessimist?

Some people view the world in black and white where everything is either wonderful or terrible, but most of us see shades of gray between those two extremes. This question will help you find out how the other person looks at life and how they approach problems.

Where do you see yourself in 5 years?

This is another question that tells a lot about who someone is as a person. It shows that you're interested in the bigger picture of their life and it allows them to talk about it without fear of judgement. They will be able to tell you their hopes, dreams, and aspirations without feeling like they're being judged by you.

What's your favorite comfort food?

Everyone has a particular dish or meal that they revert to when times are challenging or when they just want something familiar and satisfying. It can give you an insight into a person's personality and how they cope with everyday situations. For example, if someone says they love lasagna but are a vegetarian, it would show how dedicated they are to their beliefs or how strong their beliefs are.

What is your favorite season?

This question shows that you're interested in the big picture of what makes a person who they are as opposed to how much sleep they get over the weekend. It will also allow them to tell you about the season when they were happiest or enjoy most. It's nice to get this picture of where your friend sees themselves in life and it also helps them appreciate the things that bring them pleasure now, as everything does!

What was your favorite book as a child?

This question is similar to the previous one, but it will undoubtedly lead to a different answer. It's nice to have small details like this about someone you are getting to know and it allows you to see how their personality has developed over the years.

How does your job make you happy?

If the person you are talking to has a positive outlook on their work or they enjoy what they do, this is an interesting question that gives them a chance to explain why they're happy. It'll also help them appreciate themselves more and re-focus on what makes them happy after hours or in life in general!

What is your favorite saying?

It's always nice to have someone around who has a good life motto to live by and it's fun to hear what some of the popular ones are. As well as giving you some insight into their personality, it will also help you understand the moral code that they live by and what influences them.

What do you find funny?

Everyone has their own sense of humor and it can tell a lot about a person when they're sharing something that makes them laugh. It helps you understand their sense of humor and how they interact with other people who have a similar one to theirs.

How do you relax?

Everyone has their own methods of relaxing and unwinding after a long day at work or to help them get ready for the next one. This is a great question to learn more about someone and it's also a great way to learn more about how they manage stress. Relaxation isn't something we all think about very often but we do need it on a regular basis to keep us as healthy as possible!

What is the oldest story you know?

This question will help you see who the person was before they grew up and as humans, we are constantly changing so it's nice to have a reminder about where we came from in our early days. It also helps you understand the person's sense of humor and how they see the world.

If you could go back in time, what would you tell your younger self to do differently?

It's always nice to know when someone is thinking about their past and where they are within it. It also helps us as people get a better understanding of ourselves and what we think about our self-improvement (if any) or just to see how we have changed for the better.

Who do you respect?

Respect is something that is earned and most of the time, it is not something that can be given to people, it has to be given to others by them. It's also a good way to see how they view other people who they look up to and admire. Just because someone is respected by someone else doesn't mean you'll fully agree with them or like them, but it does help you understand why they are being respected by someone else.

What makes your life worth living?

Everyone wants their life to have meaning for themselves which can create a sense of fulfillment for them in life. People like to live their life in a way that they are doing it for the greater good of themselves and other people. It helps you understand their sense of compassion for others and a way of helping others to live better lives as well.

What do you dream about at night?

The dreams that we have during the night can be very vivid and can help us see our subconscious in different ways. Being able to talk about these dreams can help us find some insight into what our minds are really thinking about in the background and how we might interpret that later on in life.

What are you most proud of in your life?

Everyone has something that they can take pride in because it gives them an element of accomplishment. Being able to talk about this can help you find out what they feel is their greatest achievement in life and how it makes them feel when they accomplish something on their own.

Would you rather be smarter than richer?

Most people would rather have a higher intelligence level than having a lot of money, but some people might say that money can buy happiness and give them a better sense of fulfillment. It will ultimately show you the priorities of the other person and something important to them.

What is one thing you like and dislike about your job?

If they do not like their job, it shows that they may not stay long in the company. Although you want to be a good fit for a company you still have to have some motivation to keep yourself to keep working hard. If they do not like doing what they are doing now, then think about how much worse it would be if you were stuck working with them for the next 40 years.

What makes you angry and happy?

Angry and happy are very important because it tells what kind of person he/she is behind his/her appearance. For example: "I'm angry when I see you." or "I'm happy when your not here." on the other hand, if you're angry because they do not have a good sense of humor, then he/she is definitely someone who does not respect your opinions.

What is the best movie in the world?

Everyone has an opinion on which movie is the best in the world based on their own personal taste and criteria, so this question will help you get to know them better based on what they love. Furthermore, it will give you an insight into their personality by seeing how they react to a particular movie.

What was your favorite toy as a child?

Leaving school is not the only place where we grow up, our whole life is one big experience that shapes us into who we are. This question can help you understand how they grew up and matured among other people to understand more about their personality.

What's the most interesting thing that ever happened to you?

Everyone has an interesting experience at some point in their life and it helps them cope with different situations. It also shows how they deal with pressure in certain situations by behaving very differently from others when they're not put under extreme stress or pressure. Sharing these stories will help them feel more relaxed and comfortable talking to you, because of this question.