25 Questions To Help You Get To Know Someone Deeply

By Stephanie Kirby|Updated September 6, 2022

If you're an introvert, or even a little bit socially anxious, you know the struggle.

You yearn for a deep, meaningful connection more than anything…but you just can't seem to break past the small talk. Maybe you just don't know what questions to ask a guy. Maybe you are trying too hard to be an extrovert when you should focus on your strengths, 

Whether it's to make new friends or find a significant other, eventually you have to overcome your reserve and get into those meaty conversations about the things that matter.

Learn How To Get To Know & Better Understand People From A Professional Counselor

But where to even start?

It can be as simple as asking the right questions to get to know someone. Questions that get to the heart of someone's values, personality, and beliefs of the world without any intrusive trespass of their privacy.

Whether you're trying to strengthen a friendship that you've had for years by learning more information about this person or boosting an intimate relationship with your significant other, well-chosen questions can spark a conversation that can help you get to know them in a way you never have before.

25 Questions to Help You Get to Know Someone Deeply

What Are You The Most Proud Of?

What does this person value? Some people might consider their job performance to be their biggest achievement. Others might put more value on relationships with friends and family. Others may have wishes for things they could be proud of in the future. 

What Are You The Most Ashamed Of?

This question requires an honest look at someone's mistakes, as well as the sincerity of their efforts to improve themselves. This allows you both to take looks into how they are trying to better themselves. 

If You Could Go Back And Change One Decision In Your Life, What Would It Be?

The answer will tell you how this person has changed over time, and how her values and beliefs have shifted. This question is aimed at finding something deep in them, not something like changing the numbers on their lottery ticket or the name their parents gave them.

What Is Your Biggest Dream In Life?

Where does this person want to go in life? What country do they want to buy a house in if they could go anywhere? And can you see yourself being part of that story? Do their wishes align with your own?

What Difference Would It Make In Your Life If You Felt Completely Safe, Accepted, And Loved?

This tells you about the challenges a person is facing, and how these challenges affect him.

Do You Think Your Parents Did A Good Job Raising You While You Were Growing Up? Why Or Why Not?

A person's childhood gives a lot of information about who they are…but not nearly as much as their feelings about that childhood. Maybe they have a lot of good memories from when they were a kid, such as birthdays or sports, but they haven't opened up about how they were raised. 

What's One Thing That You Wish People Understood About You?

Sometimes appearances are deceiving especially on social media. This question brings out hidden personality characteristics and can show a lot about a person. 

What Is Your Biggest Flaw?

When answered honestly, asking this question can protect you from unpleasant surprises further along in the friendship. It also reveals what personality qualities your new friend values.

What Event In Your Life Has Shaped You Most As A Person, And How Did It Do So?

This offers valuable insight into the person's past. It may explain many decisions and behaviors as the friendship progresses that would otherwise be mysterious.

Have You Ever Treated A Person In A Way That You Regret?

And related to that: What would you do differently if given a chance?

The answer will reveal much about what she considers to be right and wrong ways of treating others, and tells you what you can expect in the course of the friendship.

Do You Think It's Possible For Men And Women To Be "Just Friends?"

Especially in cross-gender friendships, it's helpful to know exactly what the person's friendship goals are…or are not.

Would You Rather Be Rich And Lonely Or Financially Destitute With Lots Of Great Family And Friends? Why?

This is another question which speaks volumes about this person's priorities. It gives you an understanding of how much he may be willing to give to make a relationship or a friendship work. Maybe they would be fine filthy rich with just a pet by their side. This is something you may want to know. 

Tell Me About Something You Did When You Were Drunk That You've Never Confessed To Anyone.

Often, the loss of inhibition leads us to show our true colors. But what exactly are those true colors? You can either wait until the next time she drinks a little too much…or you can just ask straight out.

If You Could Change One Thing About Yourself, What Would It Be And Why?

Like the question about what you're ashamed of, the answer to this one speaks volumes about a person's weaknesses, and what he is trying to do to conquer them.

If You Knew You Would Die Tomorrow, How Would You Spend Today?

Whether it's seeing a longed-for tourist landmark or just spending the day with a group of closest friends, nothing says more about you than how you choose to spend your time…especially when that time is limited.

Are You Truly Happy?

And why or why not?

This is useful for gauging how positive and upbeat your new friend is. Is she a glass half-full kind of person? Or does he have a tendency to ruminate about negative things? And what triggers her happiness or unhappiness?

Have You Ever Been In Love?

And how do you know? What was it like for you?

Love can seem like a moving target. Everyone has different experiences and different ideas.

When You're Home Alone, And Nobody Else Is Around, How Do You Like To Spend Your Time?

Who is your friend when no one is watching? That's the person that he is likely to become once he is more comfortable around you. Maybe it is something simple like watching movies or tv, cooking an elaborate meal, reading a book, or performing another activity, but it could also be a much deeper answer. 

What Do You Want People To Say At Your Funeral?

This shows you what a person wants to accomplish in her life, as well as the kind of impression he hopes to make on others.

If You Could Have A Conversation Over Coffee Or Food With Anyone Living Or Dead, Who Would It Be And Why?

Buddha? Elvis? A deceased parent? Whatever the response, you can discover who your new friend admires the most, revealing the attributes that he values above all. Maybe it is someone from music or tv that you didn't even know he admired. This is a great way to find out more about his interests as well. You could even take the question a step further and ask who they would like to be trapped on a deserted island with to find out who they would want to be around when it matters most. 

Do You Think You're A Genuinely Good Person?

And why or why not? Make them describe who they are to get the reasoning behind their word. 

This question is a helpful gift in sorting out your friend's standards of human worth. What does she consider good? Is everyone innately good, or are most people deeply flawed?

How Did You Choose Your Current Profession?

Are you happy with your job? Would you rather be doing something different?

Asking this question helps you understand whether this person is content with his path in life. Is she making steady progress towards her goals, or is he ready to mix things up at any given moment?

If Money Were Not An Issue, How Would You Spend Your Time Each Day?

We can all safely admit that the business of earning a living gets in the way of many a hope and dream. Learn about the hopes and dreams your friend may hide underneath the daily grind of existence. Maybe they would spend it making movies, going places they haven't visited yet, or trying to end world hunger. Whatever it may be, this person will reveal a lot about themselves. 

Tell Me About Your Political Leanings.

Have they changed? How were they developed or influenced?

In some situations, you will prefer the friendship of a person whose political convictions are similar to yours. But if there is open-mindedness, you can have some engaging discussions.

What's One Thing That You Do On A Regular Basis That You Hate Doing, But Nobody Knows That You Despise Doing It?

This is a unique way to discover someone's likes and dislikes, as well as how much they are willing to give up for others or for a necessary cause.

Taking It Further

If you have trouble making social connections or developing meaningful friendships - or if you have a significant other and want to deepen your emotional connection, consider using a professional counseling service. Online counseling is an excellent way to work on your social skills even if you struggle with Social Anxiety. BetterHelp.com offers convenient online counseling that can help you meet your relationship goals - whatever they may be.

When Questions Make Conversations More Interesting

Questions personal in nature not only help you learn about someone; they make conversations enjoyable. Asking questions enables you toremember more about someone’s life while understanding the potential of where the relationship could go. Funny questions help lighten the mood, and icebreaker questions may reduce nervousness or tension. When you want to get to know someone, you may have more than one good question to ask. One thing to keep in mind when meeting someone new is to think about who you’re with and what you want to know about them. Doing so plays an essential role in coming up with intriguing date questions to encourage meaningful conversation.

Questions help you get to know each other but also help you become comfortable in each other’s company. Consider casual questions about their career interests or hobbies. Sometimes unconventional questions enlighten the mood while taking you by surprise with an unusual answer. A common question people ask may include what they look for in a life partner. Many people love this question because it may hint at the qualities you both seek. A question is great when the person you’re with answers with enthusiasm and openness. You know you’re asking the right questions when the conversation leads to deeper questions.

Asking Questions With Confidence And Intrigue

It is common to avoid mundane questions when wanting to get to know someone. People may worry they come off as dull during date night. A boring question may be an annoying question if others have asked the person many times. The key to asking the right questions includes considering what you want to know about them. It shows you are genuinely interested in getting to know them, drawing you closer.

To help you get comfortable with asking questions, think about the types of questions you want to ask during your date, and consider 10 questions to get to know someone. Review them with a friend for feedback before asking that special someone. Consider icebreaker questions to ask when things get awkwardly quiet. Sometimes people purposely ask funny questions just to see a smile or to help someone feel more comfortable. Mix up your questions with simplicity and creativity.

Sometimes curiosity may lead to asking a philosophical question. You may be interested to learn their views on religion, faith, and the meaning of life. A philosophical question may be about happiness or something to provoke deep thoughts.  An example of an interesting question on this subject that is commonly asked is, do you believe true love exists? Many love this question because it gives an idea of what they think true love represents.

Remember, your questions help start and keep conversations going. When getting to know someone new, keep the conversation mutual with a positive vibe or tone. You can also get professional advice about how to ask questions by talking to a counselor or therapist.

Below are some commonly asked questions on this topic:

What are 20 questions to ask to get to know someone?
What questions should I ask in 20 questions?
What are cool questions to ask?
What are 50 questions to ask?
What are some juicy 21 questions?
What are 10 questions to ask?
What is 21 questions to ask a guy?
What are 21 questions to ask a girl?
What are 10 questions to ask a girl?

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