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One of the best ways to get to know someone better is by asking open-ended, deep questions.
Even though many questions might sound generic and it may only incite small talk, the responses are usually very revealing. They give you a glimpse into a person’s true nature. Sometimes, answers to personal questions will even reveal what an individual often hides from others or is afraid to tell most people.
Sounds heavy, right?
But really, if you want to get to know a person beyond the basic biographical information of their name, birth date, and hometown, then you need a list of deep questions to ask during conversations.
Deep questions are not only ideal for getting to know others better; you can also use them to become better acquainted with yourself, especially if you are searching for your purpose in life.
So with that in mind, this post contains 371 deep questions that will help you:
Get answers to reveal a person’s core values and true character
Remember that although these questions are great for getting the conversation going, you must be attentive to the answers and ask for details when necessary. As much as possible, even with the more serious questions, keep the “interrogation” light and lively. (Which is why we highly recommend you focus on the practice of mindful listening.)
OK, let’s get to the questions you can ask someone…
If you’re looking for ways to know a girl better, these get-to-know-you questions can help you dig further and reveal more about her personality.
These questions help keep your conversation going, and at the same time, allow you to discover more about her. With these questions, you’ll learn about her life’s story and how it has shaped her in the present, what her tastes are, and how she views other people, among other things.
You can use these more personal questions to start up new conversations instead of revisiting the same old conversations again and again. New topics will lead to learning how someone really feels about something, and this small talk can ultimately lead to a deep and meaningful conversation that can lead to a healthy relationship.
If you were given three things to make you happy, what would these be?
How would you rank the following in importance: family, career, love life?
Which would you prefer: having a baby without a partner or a partner without a baby?
What was your experience about being “mansplained,” and what did you do about it?
Who was your favorite cartoon character when you were a kid?
Do you think God is real, and why?
Do you believe in giving people second chances, and why?
Do you think people fall in love because the right person has arrived, or because the time is right (regardless of whom the person is that they fall in love with)?
When was the last time you spoke with a classmate from high school?
Are you left- or right-handed, and would you want to switch?
What subject were you good at in high school?
What was the most memorable experience you had in elementary school?
Do you find it difficult to admit that you are wrong, and why?
Do you get excited or scared when meeting new people?
What is your secret hobby that others would consider weird?
How do you cope with stressful situations?
Is there anything that you would like to change about yourself?
What musical instrument do you know how to play?
Who or what inspires you?
Which would you prefer in a romantic partner: a dreamer or an achiever?
What is your favorite part of a house, and why?
Who is the fictional character who closely resembles you in terms of attitude?
When you were a kid, what did you say you wanted to be when you grew up?
What was the title of the first movie you watched in a movie theater?
When was the last time you slept outdoors?
What is something that you are proud of about yourself?
What song do you often sing in the shower?
What do you feel is the right age for people to get married?
What would be your super villain name and your powers?
What three non-electric or non-automatic items would you take on a deserted island?
If “hello” were to be replaced by another word as a greeting, what word would that be?
What is the weirdest thing that your family does together?
What was the most embarrassing thing that you’ve done for a friend?
What task would you really fail at doing?
What is your definition of a “perfect life”?
What would be the title of the movie showing your life from birth up to present?
What fashion piece would you invent for women?
What is the single most important thing people should do for the planet?
How do you define evil, and do you believe that a person can be evil?
What do you think are the two things that prevent people from realizing their dreams?
Would you lay down your life for someone?
What word or term do you wish to know the meaning of?
What makes you nostalgic?
Do you believe that each of us has a soul mate?
How would you live your remaining days if you found out you had only a week to live?
Do you listen to other people’s advice, or do you prefer figuring things out yourself?
What is your favorite motivational quote?
Imagine that you are tasked to re-design society – what changes would you make?
What’s the perfect day for you?
Would you wait for the sun to rise or for it to set, and why?
If you were born in another era, when would that period in history be and why?
Have you made someone cry?
What is the most astonishing act that a person can do for you?
What is more important: being true to yourself regardless of who gets hurt or considering the consequences of your actions on other people’s lives?
If you die tonight, would you pass away fulfilled or unsatisfied with life?
90 Deep Questions to Ask a Guy
As with the get-to-know-you questions for a girl, the following list questions has the potential to reveal the true personality of the guy you are talking to.
Ask follow-up questions to the answers given to you. Learn to read between the lines in his answers, as sometimes the things that are being said are colored by the things you want to hear.
How would you describe the perfect day?
Is there any decision that you feel guilty about making in your personal life?
What movie influenced you the most?
At what age do you think people should think of settling down?
If you were stranded on a deserted island, what three items that are not electronic or automatic would you take with you?
If they made a movie about your life, who would you choose as the director and why?
What ability do you possess that you’d think others would find amazing?
Have you ever stayed up all night to wait for sunrise?
When was the last time you slept under the stars?
Would you rather be a world-famous pro-MMA athlete or the president of a country?
Can you remember the last time you cried, and what was the reason?
Who do you feel is your closest confidant among your family members?
If you were given a million dollars today, how would you spend it within three days?
What two items would you need to survive an apocalyptic zombie invasion.
When you were growing up, which superhero was your favorite, and why?
What is your funniest memory of high school?
How would you spend your remaining time if you found out you only had 10 days left to live?
What’s one item you’ve recently crossed off your bucket list?
Do you have a favorite place in the world, and where is it?
One of the benefits of answering deep questions is that you get the chance for self-reflection.
Self-reflection points out exactly where you are right now in your emotional landscape. It can also remind you about the goals you’ve set for yourself and force you to acknowledge whether you’re fulfilling them or not.
When was the last time I lost track of time while doing something?
What was that activity?
How do I want people to describe me at my funeral?
Bonus Round! A Few Questions to Ask Kids
While some of the above questions are deep and meant to spark a more meaningful conversation with someone, it is also always fun to talk to kids. Maybe they have a favorite movie they want to tell you about, or they have an embarrassing moment to share.
The following questions for kids are great conversation starters. They are interesting questions, funny questions, personal questions, and good questions to ask a younger audience.
Can you remember the last time you laughed so hard, you snorted?
How do you eat an Oreo?
What is your favorite letter of the alphabet?
Would you rather have to scream or whisper?
Do you have a favorite chore you like to help with around the house?
What is your favorite movie? Actor?
Would you visit the moon for one day if you could?
What is your perfect dessert?
Do you like board games? Which ones are your favorite?
Final Thoughts on These Deep Questions to Ask Someone
Well, that’s a wrap!
The answers to these questions will hopefully surprise, inspire, and move you.
Before we part, I’d like to leave you with this reminder.
In asking these deep get-to-know-you questions, there are two essential things to consider:
Your sincerity – Is your purpose for asking these questions truly to get to know the person better?
Your confidentiality – Some, if not most of the answers to these questions will be sensitive, and they will be given to you by the person in confidence. Remember to keep their answers private.
Hopefully you picked up a few great questions to ask during your next conversation, and hopefully, the responses will help you build a deeper connection with someone. (If you're looking for more, here are some questions to make you think.)
