25 Questions To Help You Get To Know Someone Deeply

By: Stephanie Kirby

Updated October 04, 2021

Medically Reviewed By: 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.

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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.

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.

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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.

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. 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.

Frequently Asked Questions (FAQs)

What should I ask in 20 questions?

If you feel stressed about what types of questions to ask, take a deep breath. They are basically conversation starters to help you get the conversation flowing.

With that in mind, good questions are often ones that are open ended. This means that the other person can’t answer with a simple “yes” or “no”. They have to expand on their answer, which helps you get to know them more. It may even lead to follow up questions.

If you’ve read the questions above and are still wondering what are some other great questions to ask, consider using the following:

  • What recurring dreams do you have?
  • What has been the best moment in your life?
  • What family member were you the closest with growing up?
  • What would you consider a dream job?
  • If you were creating a bucket list, what would be your top 3 things?
  • Do you have a guilty pleasure?
  • If you could be one fictional character, who would it be?
  • What are the deal breakers for friendships?

How do you get to know someone deeply?

The best way to get to know someone deeply is to learn about them. It means you need to go beyond the small talk. Don’t be afraid of deep conversation. However, before you start with a lot of personal questions, begin with topics that more people are comfortable with. As you get to know a little more about them, it will help you know what other good questions you can ask that they would be comfortable answering.

Getting to know someone deeply requires deep questions, not just sticking with the small talk. It also means that you need to be willing to share your answer to personal questions as well.

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What are some deep questions?

If you want to know someone deeply, it helps to know good questions that can help get the conversation going. Some open-ended questions that you can use include:

  • What’s your favorite memory from your childhood?
  • What’s one thing that you learned from your best friend?
  • Do you think that having your dream job with little pay is better or earning more money doing a job that you don’t mind?
  • What qualities do you think are important for a healthy relationship?
  • What’s your idea of a perfect day?
  • What’s the best piece of advice that you’ve ever received?
  • What does it mean to be religious or spiritual to you?
  • Which family member made the biggest impact on your life?

What are good questions to get to know a guy?

Knowing the right questions to ask can help you start to get to know a guy better. Some men may not be as comfortable jumping into deep conversations that require them to share a lot of their feelings. It can be best to try conversation starters in the beginning to get to know them little by little.

Some good questions to consider for conversation starters could include:

  • How many bucket list things have you done in your life?
  • What’s your favorite way to spend a Saturday?
  • What’s your favorite holiday and why?
  • What’s the silliest irritational fear that you have?
  • Where’s your favorite place to go on vacation?
  • What do you like to spend time doing when you have free time?
  • What’s the best ice cream flavor in your opinion?

When you are just getting to know someone, you can use the conversation starters of “What’s your favorite...?” for many different things. This will help you get to know their preferences. And once you know things that they like, it can help steer you into good conversation topics to focus on.

What are interesting questions to ask?
When you are looking for to get to know someone, you’re going to want to keep your questions interesting. If you start firing off boring questions to break the ice as conversation starters, the other person may quickly lose interest in talking. This is why it can be helpful to ask questions that start with “What’s your favorite...”. This helps you quickly get to know their preferences so you can ask good open ended follow up questions.

These questions should be tailored to the things that you already know about them. Start with some easy conversation starters to learn the best conversation topics for that person and then slowly start to work towards understanding them better in that area.

What are some questions to ask your crush?

When you’re looking for questions to ask someone that you’re crushing on, they may be different questions than you would ask of a new coworker or the person sitting next to you on the subway. You probably want to find some questions that are a little bit flirty instead of just the basic conversation starters that you’re used to.

Try asking some open-ended questions to learn about their dating preferences. Ask things like “What’s your favorite restaurant?” Or, “What’s your favorite place to go on a date?” Asking the “What’s your favorite____?” questions can give you good insight into your crush.

Focusing on conversation starters will not only help you know what conversation topics are good ones to focus on with your crush, but they’ll also help you know if they’re a person you want to keep investing your time into. If they are, eventually, you’ll want to ask questions about their family members, childhood, and more serious conversation topics as well.

How do you flirt over text?

Flirting over text doesn’t have to be that different from flirting in person but without the body language, it can be something that takes a little more effort. Don’t feel that you always need to play it safe. If you are flirting with your crush vs a person you’re dating will determine the types of texts that you send.

Remember that flirting should be fun. If you’re not having fun when you’re writing and sending your texts, the person on the receiving end isn’t going to pick up on that either. You can still use questions as conversation starters over text.

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