25 Questions To Get To Know Someone Deeply

By Stephanie Kirby

Updated January 22, 2019

Reviewer Kelly Kampf

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

You yearn for a deep, meaningful connection…but you just can't seem to break past the small talk.

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.

But where to even start?

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

Whether you're trying to strengthen a friendship that you've had for years 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.

Source: pexels.com

25 Questions to 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.

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.

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.

What is your biggest dream in life?

Where does this person want to go in life? And can you see yourself being part of that?

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 says a lot about who they are…but not nearly as much as their feelings about that childhood.

What's one thing that you wish people understood about you?

Sometimes appearances are deceiving. This question brings out hidden personality characteristics.

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.

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.

Source: pexels.com

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.

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 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.

Do you think you're a genuinely good person?

And why or why not?

This question is helpful 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.

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.

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