25 Deep Questions to Get to Know Someone

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October 26, 2020

Getting to know someone deeply calls for an objective-oriented communication approach, as opposed to a casual one. You need to have a specific set of deep questions to get to know someone. They will naturally steer your communication towards helping you understand the other person without making it feel interrogative.

What achievement are you most proud of?

The question is an effective one in learning the orientation of a person’s interests. It’ll tell you what they value and hold dearly the most.

What’s the most embarrassing thing or moment of your life?

When answered honestly, you will get a glimpse of the person’s response to fault and shortcomings. It is a fundamental attribute in any level of relationship.

If given a chance to change one decision you’ve made, what would it be?

Acknowledging our wrong shots is a vital ground for growth, and this question enables you to understand the person in this regard. How ready are they to accept their mistake and take a turn around? 

What’s your biggest goal and dream in life?

Two people cannot seamlessly walk together if they have nothing in common. Besides unveiling the extent of their dream, his question will help you see whether you have a place in the person’s future or not. 

What difference would it make if you felt totally cherished and loved?

Almost every person has some form of insecurity, and this is the question to help you know what their insecurity is. The insights will help you in handling your relationship, well, if it progresses.

Do you think your parents did a great job raising you as a kid? Why or why not?

A person’s childhood models their personality, and this question will help you understand why the person is the way he/she is.

What’s one thing that you feel people don’t understand about you?

Self-image plays a huge role in relationships, and this question will help you get the person’s viewpoint of themselves. 

What is your biggest weakness?

Being conscious of our flaws and weaknesses is priceless. Knowing each other’s weaknesses can save a relationship.

What occurrence in your life has influenced you most as a person, and in what way?

Our experiences shape us, and this question will help you learn of the contributing factors to the person’s personality.

Have you ever treated a person in a way that you regret?

It is a question that will help you gauge the person’s value for people. If they’ve ever done wrong to someone and they own it and wish they could undo it, that can show you what you can expect from them.

Do you think men and women can be “just friends?”

If there’s a question that’ll help you unveil a person’s relationship goals, more so for opposite-sex relationships, this one will do.

Would you rather be wealthy and lonesome or financially destitute with a great family and social life? Why?

It is a question that’ll help you weigh what the person values most in life. Some people value money more, and some value their social lives more.

Tell me the craziest thing you did while drunk that you’ve never confessed to anyone.

Some people can do anything when they’re drunk. This question will help you gauge a person’s tipping point when they’re inebriated.

If you could change one thing about yourself, what would it be, and why?

This question should point to the person’s weaknesses. Understanding their weaknesses will make for a better relationship as you’ll be able to understand their actions and responses.

If you knew you would die tomorrow, how would you spend your last hours?

Again, this is a question that’ll shed more light on what they value most. When all the hustle and bustle of life is by-passed, what does the person live for?

Are you genuinely happy about yourself and your life?

If the person is unhappy with themselves as a single person, they most probably will bring that energy into a relationship. Answers to this question will help you better relate with the person and grow a healthy relationship.

Have you ever fallen in love?

Previous life experiences may affect a person’s mentality and attitude towards relationships. Learning about the person’s previous experiences will help you know how to handle your relationship.

When you’re home all by yourself, how do you like spending your time?

Someone said that we are our real selves when we’re alone. Asking this will help you understand the person’s personality and what they love.

What do you want people to say at your funeral?

This question will give you insights regarding the person’s innate desires, the things they would want to achieve, and how they would love to impact the world around them.

If you could have an opportunity to talk with anyone living or dead, who would it be?

If you want to know what motivates and drives the person, then this question will enable you to do just that. It’ll also help you understand their character as their attributes would be more inclined towards the personality of the role model. 

Do you consider yourself a genuinely good person?

This question will help you understand the person’s moral values and what they consider are the hallmarks of a good character and personality.

What influenced you to choose your current profession?

Asking this question should help you unearth whether the person is happy with their professional life or not. It is a factor that can influence a relationship either positively or negatively.

If money were not a problem, what would you be doing each day?

If you want to know what really matters most to the person and what their heart is out for, then this is the question to ask. The busyness to make a living denies most people the opportunity to live out their dreams.

Tell me about your political leanings.

For any relationship to flourish, having similar social and political leanings goes a long way. You’ll avoid unnecessary arguments that might escalate to toxic levels.

What’s one thing that you do regularly and hate doing, but nobody knows that you detest doing it?

This question will shed more light on the person’s dedication and degree of sacrifice for others. 

Taking It Further

Some people are naturally introverted, while others may find it challenging to engage in meaningful conversations towards building relationships. If you’re one of them, don’t beat yourself down for it, it’s natural, and there’s room for improvement. Professional counseling services help individuals with social anxiety, equipping them with better social skills essential for achieving your relationship goals.

FAQ Section

How do you get to know a person deeply?

Knowing someone deeply goes beyond knowing their rudimentary attributes. You have to go deeper by asking deep questions to get to know someone regarding who they are, what they believe in, and what they stand for. However, starting with deep questions may come off as unnatural and interrogative. You want to be as inviting as possible. Ask open-ended questions that will give the person room to go deeper into talking about themselves.

What questions should you ask your crush?

Crushing on someone denotes your prospects for a relationship, and therefore this should chart the course for your conversations. You have to ask questions that will build mutual interest, questions regarding what the person likes, their favorites, and what they detest.

How do you flirt in a text conversation?

There’s no significant variation between flirting in person and over text except for the absence of body language. You can send flirty texts that express your interests from the start without putting the other person off. The trick is being natural, letting your personality show, and not being afraid to express yourself.

Kate Skurat

Kate Skurat

Licensed Mental Health Counselor

Washington, United States

Kate has a B.S. in Psychology and M.A. in Clinical Psychology from Pepperdine University and has worked in healthcare since 2017. She primarily treated depression, anxiety, eating disorders, trauma, and grief, as well as identity, relationship and adjustment issues. Her clinical experience has focused on individual and group counseling, emergency counseling and outreach. Read more.

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