Here at WorkFun, we always suggest using questions as part of a debriefing of group and team building activities. Of course personal questions are not limited to ice-breaker or fun games, but are a great tool to get to know a co-worker, acquaintance, and also for someone you want to get to know better. In life it is often difficult to make a connection of sorts with people we don’t know that well. So therefore, we thought we would help you out with a whole bunch of questions to get to know someone better.
Please remember when asking the questions, more important than the question itself is how you listen to the person answering your question. Listening is a wonderful skill that can be developed and plays a significant role in strengthening relationships.
Although there are no hard and fast rules, the first batch of questions are more for someone you have only just or recently met, or somebody that you don’t know well. These questions are casual in nature yet still interesting and safe to use.
If you had the choice to not sleep without it affecting your health, how would you spend all the extra time that you now have?
What is your most valuable or sentimental item of clothing that you have?
If money was not a deterrent, what hobby or sport would you like to do?
What would be the main feature if you could choose any house to live in?
How many days per week or month do you get to play sport?
What fictional character would you most want to be?
What type of job will you be very bad at?
When last did you climb up a tree?
If any activity that you do became an Olympic sport, what is it and will have an outside opportunity to earn a medal for it?
What habit of others really annoys you the most?
Deciding on a job for yourself, what would you excel at?
Is there a skill you would like to learn?
If you had to go on a breath-taking adventure, what would it be?
Think of your dream home, if you had more than enough money, what would you build?
Do you have a preferred drink?
If you could, what country or state would you revisit?
Are there any songs you know, that you can sing off by heart?
If you could live in any movie or game world, what would you choose?
Have you ever discovered anything you feel is amazing?
What type of person are you, one who is early or are you always late?
Did you have any pets when you were young?
What type of help do people come to you for?
Does something excessively consume your available time?
Is there something you want to learn more about?
If you were cryogenically frozen and awoke 100 years later, what would be the first question you asked?
Sometimes it’s the small things that matter, what makes your day more pleasant?
Do you have a favourite singer or band you listen to often?
Name the shows you are interested in?
Is there a TV channel you think should be created, but doesn’t exist?
Do you have somebody you look up to and what accomplishments have they reached?
If you could choose, what age would you want to remain at?
Is there a movie or TV show you won’t ever watch?
What does your perfect weekend look like?
Is there something in your life you cannot live without, that others think is a luxury?
Are you famous for something?
Is there anything you enjoy doing the old-fashioned way?
What category movie or book do you enjoy the most?
Do you enjoy people watching?
Have you formed an opinion on anything lately?
Do you have a single ‘best’ day in the year?
Do you have interests that nobody else has heard of?
What do you do in order to relax after work?
Tell us the name of a book or series you think is the best?
Have you ever travelled far from home?
Out of all you’ve seen so far, what is the most encouraging?
Is there a question people ask you, that you find really annoying?
If you could give a 40-minute presentation on a subject without preparing, what would it be?
Imagine yourself as a dictator on a small island somewhere, what ridiculous things would you implement?
Is there something you think that everybody needs to put on their bucket list?
Out of these two options, which would you prefer doing? White Water Rafting or Hang Gliding?
Is there a dream car you would like to own?
If you had to spend money on something worthwhile, what would it be?
There are many popular even obsessive things in the world, what is the one thing everybody just loves, but you just don’t understand what the big deal is?
Is there something happening in the next 10 years you are excited about?
Can you tell us where the most remarkable destination is you’ve been to?
Is there something in your life you have always wanted to do, but have never gotten around to?
During the past week, is there something that happened that stands out?
Out of all the entertainment you have come across, is there something you would like to experience for the first time all over again?
Imagine every job had the same working times and salary, what would you then choose to do?
Have you ever done anything amazing, and there was nobody around to witness it?
Looking back to a year ago, do you think things have changed in your life?
How do you start your day, and do you think it is the best way?
Do you have any peculiarities?
Is there anything you would highly rate?
Is there a trend or craze you wish would come back?
Is there a piece of art you admire the most?
What art form do you like the most?
What would you never want to change?
Out of all the cities in the world, which one would you want to live in the most?
Considering various movie titles, which one most represents your life now?
This bunch of questions are a bit deeper and more personal. Depending on your personality, you may or may not want to ask these questions to people only recently met. These are great questions friends that you want to get to know better.
Is there a reason you chose the work you are doing now?
In your opinion, how can a person better utilise their time?
If by some way you become a woodworking genius, what would you create?
Where have you ever felt the most relaxed and at peace?
Is there a time in your life, where you have felt the most fortunate?
If you had a choice, is there somewhere else you would rather come from?
Have there been instances where you have needed to unlearn something?
Is there anything exciting happening in your life, a few months from now?
Surfing the internet, is there a website you visit more frequently than others?
Is there anything you want that you can’t afford?
On your time off, where do you go?
What place would you go to, if you could spend all your time there?
Where did you grow up and what is special about it?
How old do you want to become?
Is there anything you do that could make you famous one day?
What do you want to achieve the most?
Is there anything extraordinary you can do?
Do you wish you knew more about something?
Is there an important question you would like answered?
In order to learn more about somebody, what questions would you consider asking?
Has something ever changed your mind about an important issue?
Tell us about the best compliment you have received.
What would you do, if you were the only person left on earth?
Do you have somebody you look up to?
How would you want your epitaph to be worded?
Is there something you wish you had grown out of?
What place or situation would make you the most uncomfortable?
Is there something you have done that you thought was ridiculous, but it actually turned out great?
If you decided to write a book, what would it be about?
Is there something you have done, but will never do again?
What thoughts go through your mind the most?
Circumstances can mould you into who you are, what events do you think had an influence on your life?
Do you think there is something you can do better at?
Some people say that in this world, there are two types of people, what do you think they are?
Is there anything you have come across that seemed very strange to you?
Is there something you are absolutely sure you will never experience?
Is there a ridiculous accomplishment in your life, you are pleased with?
If there is one rule everybody has to keep, what rule would you make?
Is there anything you are addicted to?
With all the stereotypes in the world, is there one that you live up to?
What project do you have going that never seems to get done?
Is there something you are afraid of, as you get older?
Do you have a favourite aroma?
Describe your most scary monster?
Do you like a certain artist or song, but would never admit it?
If you new you were going to die in the next hour, what would you want to do before it happened?
Have you read a book that affected you in a major way?
If you could change your name, what would it be?
Many compare life to a game, if this was the case, what rules should there be?
Do you have, or have you ever had an out of the ordinary friend?
Do you give to charity?
What would your friends consider unique about you?
Are there risks you would consider taking and why?
Is there something you just cannot get right, no matter how hard you try?
If you had the power to get everybody in the entire world to do one thing, all at the same time, what would it be?
Is there anything you take for granted?
If you could experience yourself as a roommate, what would be the most annoying things about you?
Is there anything about yourself that you are self-conscious about?
When considering your personality, what is your best quality and the worst?
Thinking back on your life, is there a time you remember when a stranger did something small for you, but it affected you in a huge way?
What gets you excited the most?
Is there something challenging you are facing currently?
Are you afraid of anything?
What advice have you received that you consider the best and worst?
Imagine there is a clock counting down to something, if you could choose, what would the something be?
What do you think a good life involves?
Is there something you know is wrong, but you have no proof to back it up?
Have you been on an adventure lately? What was it?
What makes you feel completely alive?
What gift you’ve received stands out from the rest?
If you wrote an autobiography, what would your chapter headings be?
Describe your family and what you love best about them?
When you die, what will your last words be?
Statistically speaking, what would you want to see happening in your life?
Do you have three favourite numbers?
If you won two million rand, what would you do with it in order to have the most impact on people?
Imagine yourself in solitary confinement for six months, in order to remain sane, what would you do?
The last few questions are very personal. They are perfect for getting know someone you already know well. You can ask them to close friends and people you are in a relationship with.
Is there anything horrible you would recommend people try at least once?
Is there something in your life you have become resigned to?
Is there a time when you saved somebody’s life?
Can you point out some critical moments that had an impact on your life?
If you were to meet your polar opposite, what would they be like?
Are you good at something you are embarrassed about?
Name the three most interesting things about yourself?
Do you have a scars, which one has the best story?
If your life was a book, what would the current title be?
Out of all the lessons in your life, what would you consider the most difficult?
Is there a mistake you make and never learn from, so you make it over and over again?
Is there something about yourself, other people think is weird?
How do you think other people see you?
Out of all the things you have done, what makes you the proudest?
Imagine that you could make a short call to yourself at any point in your life, when do you think would be the best time and what would you say?
Are you a part of any popular crowds and is there anything that annoys you about them?
What doubts keep coming up to haunt you?
When your gone, what do you want others to remember about you?
Do you have your own ‘personal rules’, which you always keep?
Is there something in your life that you regret? Or, is there something you should have done but never got around to it?
What fragrance would you want to wear all the time?
What do you consider the greatest thing about you?
Every time you think about it, what challenges your mind the most?
What are the best traits you inherited from your parents?
Is there a responsibility you don’t want in your life anymore?
What do you consider the most important thing in your life?
What aroma would you compare your childhood to?
Name three major accomplishments you wish to achieve in this lifetime. Are you close to achieving them?
If you could chat with your younger self, what would you say? In ten years’, time, what would you want to tell yourself?
What is your role amongst your friends?
What will your family and friends say you are famous for?
In your life so far, what lesson has had the most impact on your life?
What do you think is your most juvenile behaviour?