Deep Questions to Ask to Truly Get to Know Someone

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Have you ever wanted to get to know a person better, but struggled to find the right words? “How’s your day?” sounds too routine and effortless while “Where do you see yourself in ten years?” gives off interview vibes. Fret not – this article dives into a variety of deep questions to ask someone to improve interpersonal closeness. There are questions that have helped participants in a well-known experiment to feel closer to each other, as well as questions that you may ask a loved one or friend to build closer bonds with them. The article then concludes with some final tips for you to think about before starting such conversations.

Deep Questions from a Research Study on Interpersonal Closeness

In 1997, researcher Arthur Aron and his team conducted what is now a famous experiment aimed at generating interpersonal closeness. Over 45 minutes, some participants were tasked to engage in small talk, while others were asked to take part in self-disclosure talk. The study demonstrated that people felt closer to one another after self-disclosure, as compared to small talk. What made this study so interesting and popular was the list of questions provided for the self-disclosure task (as opposed to the small talk task). There were 36 questions in total, which were divided into three sets of 13 questions each, with increasing levels of self-disclosure required from participants. People were fascinated at the idea that these lists of questions could help them to feel closer to someone else. The three sets of questions are as follows:

First Set of Questions

  1. Given the choice of anyone in the world, whom would you want as a dinner guest?
  2. Would you like to be famous? In what way?
  3. Before making a telephone call, do you ever rehearse what you are going to say? Why?
  4. What would constitute a “perfect” day for you?
  5. When did you last sing to yourself? To someone else?
  6. If you were able to live to the age of 90 and retain either the mind or body of a 30-year-old for the last 60 years of your life, which would you want?
  7. Do you have a secret hunch about how you will die?
  8. Name three things you and your partner appear to have in common.
  9. For what in your life do you feel most grateful?
  10. If you could change anything about the way you were raised, what would it be?
  11. Take 4 minutes and tell your partner your life story in as much detail as possible.
  12. If you could wake up tomorrow having gained any one quality or ability, what would it be?

Second Set of Questions

  1. If a crystal ball could tell you the truth about yourself, your life, the future, or anything else, what would you want to know?
  2. Is there something that you’ve dreamed of doing for a long time? Why haven’t you done it?
  3. What is the greatest accomplishment of your life?
  4. What do you value most in a friendship?
  5. What is your most treasured memory?
  6. What is your most terrible memory?
  7. If you knew that in one year you would die suddenly, would you change anything about the way you are now living? Why?
  8. What does friendship mean to you?
  9. What roles do love and affection play in your life?
  10. Alternate sharing something you consider a positive characteristic of your partner. Share a total of 5 items.
  11. How close and warm is your family? Do you feel your childhood was happier than most other people’s?
  12. How do you feel about your relationship with your mother?

Third Set of Questions

  1. Make 3 true “we” statements each. For instance “We are both in this room feeling…”
  2. Complete this sentence: “I wish I had someone with whom I could share…”
  3. If you were going to become a close friend with your partner, please share what would be important for him or her to know.
  4. Tell your partner what you like about them; be very honest this time saying things that you might not say to someone you’ve just met.
  5. Share with your partner an embarrassing moment in your life.
  6. When did you last cry in front of another person? By yourself?
  7. Tell your partner something that you like about them already.
  8. What, if anything, is too serious to be joked about?
  9. If you were to die this evening with no opportunity to communicate with anyone, what would you most regret not having told someone? Why haven’t you told them yet?
  10. Your house, containing everything you own, catches fire. After saving your loved ones and pets, you have time to safely make a final dash to save any one item. What would it be? Why?
  11. Of all the people in your family, whose death would you find most disturbing? Why?
  12. Share a personal problem and ask your partner’s advice on how he or she might handle it. Also, ask your partner to reflect back to you how you seem to be feeling about the problem you have chosen.

It is noteworthy that as the pairs of participants in the study asked each other the self-disclosure questions, they both had to answer each question. In other words, it was neither a one-way street nor a question-and-answer session in which only one party had to divulge information. This makes sense – it is often easier to share our true thoughts or feelings with someone when they have demonstrated the same vulnerability with us.

Also, while these questions may be helpful conversation starters, it is important to keep in mind that this experiment was conducted in a laboratory setting, and it was not the study’s aim to explore interpersonal closeness in romantic relationships over time.

Deep Questions to Ask

Other Deep Questions to Ask a Loved One or Friend

Given that the 36 questions above resulted in interpersonal closeness among participants in a research setting, you might be wondering what are some other deep questions to ask someone you are already acquainted with, such as a romantic partner or close friend. It might even feel like you have exhausted all the conversation topics you can think of. If this is you, here are some suggestions that you may wish to try.

How do you define success?

There are various definitions of what it means to succeed. Success can be anything from money and status symbols to having children and teaching them specific values. They can also be having good work-life balance, for example. None are right or wrong; they are just different. It can, however, be insightful to get a sense of how aligned your benchmarks of success are, especially if this is someone with whom you are planning a future.

What makes you feel loved?

What we think we know about our partner’s needs may not always be accurate. For instance, instead of the standard chocolates and flowers, our partner might have appreciated it more if we had simply put our mobile phone away and truly focused on what they were saying. Instead of assuming or guessing what your partner needs, why not ask them directly what makes them feel loved? We all have various preferences after all. Their answer might even surprise you.

How do you manage your emotions, especially the “heavier” ones?

Each of us may have a different combination of coping strategies which we engage in consciously or unconsciously. Some common examples include exercising, taking a walk in nature, listening to music, confiding in family or close friends, managing one’s expectations, and having regular therapy sessions.

In general, how do you think conflicts between family members should be resolved?

This question might also provide you with more information on how comfortable a person is with managing difficult emotions. Most of us dislike conflict and find it uncomfortable – the difference lies in how we respond when it occurs. Do we address it assertively (eg talking calmly, being mindful of everyone’s needs), or do we engage in aggressive (eg shouting, demanding), passive (eg avoiding conflict at all costs), or passive aggressive (eg using guilt trips) behaviours?

What are three values that you find most important in life? How did these values make it to the top of your list?

Given that everyone has different priorities in life, it might be interesting to explore how your partner’s experiences have shaped their value system over time. This question may also lead to some “aha” moments as you begin to understand why some things might seem to mean more to your partner or friend. For example, if a person highly values respect for others’ time, then having to meet someone who is habitually (and unapologetically) late can be a very frustrating experience, even if the person is only slightly late.

Ideally, how would you like the people closest to you to describe you?

Human beings are hardwired for social connection. As such, most of us want to know that we have had an impact on those around us, and that we matter.

What do you like best about me?

You can take this question one step further by going beyond the obvious physical qualities of a person. Aside from those, what does your partner or friend like most about you? It could be a habit of yours, something about the way you communicate with them, how you treat others, or one of the values you hold dear, for instance. This question also gives you a sense of what is important to the other person.

What are some boundaries that you think are important to set in life?

There are many different types of boundaries, such as physical, emotional, spiritual, sexual, financial, intellectual, time, and material boundaries. Some of us might have started setting boundaries earlier in life, while this process may have only been started later for others. People have also got varied ways of implementing and communicating their own boundaries. 

So far, what is one of your happiest memories in life?

It can be so easy to get caught up in the hustle and bustle of life that the good times slip our mind. This is a lighter question that can bring back some nostalgia.

If there was one thing you could change about yourself, what would it be?

Once again, you can take the question to a deeper level by moving beyond physical attributes. What underlying struggles, hopes, or dreams might there be, behind this question?

Deep Questions to Ask

Who inspires you most in life?

This can be someone they know in real life, a famous person they have heard of, or even a fictional character from books or movies. What makes this individual stand out to them, among the billions of others whom they could have chosen from?

Can you tell me about a time when you laughed until you cried? What happened then?

This is another light-hearted question to mix things up and add some laughter. It could be a memorable moment from their childhood, or as recent as this week. Your list of deep questions to ask someone need not always be solemn. A good balance of questions may help the other party open up more easily. 

What is a pet peeve of yours and why?

We all have pet peeves; they are perfectly normal. These can be anything from being stuck behind slow-moving people at peak hour to blatant queue cutting. Sometimes, without realising it, the smallest things can annoy us the most – another common experience.

What are some of your couple goals?

While each relationship is unique, this question may spark some ideas about couple goals that your partner and you might want to work towards in the future. What would the both of you like to see in your relationship? How might you be able to achieve that?

What are some quotes that are memorable to you?

Our favourite quotes may be from philosophers, movies, books, TV. They may even be things that our loved ones have said to us that left an impact.

In general, what are your thoughts about expressing emotions?

This is where family upbringing, culture, and one’s own individuality intersect. In some families, children may have been taught how to acknowledge and explore their feelings. Adults in the household may also have modelled such habits for children to learn from.

On the other hand, some of us may have grown up in households where emotions, particularly the more difficult ones, were buried deep and not talked about at all costs. There may also have been expectations about how much we could tell others about the ongoings within the family; “don’t wash your dirty laundry in public” is one such example. Gender may also play a role, if children were brought up to believe that “boys don’t cry”, for instance.

What energises you?

Well, other than coffee, that is. It might be a long-forgotten hobby, a sport, catching up with good friends, certain types of music or art, laughing at a pet’s silly antics, or anything else that gets you into a state of flow. A state of flow occurs when a person is fully immersed in what they are doing, or as they say, is “in the zone”.

If you could give advice to the you of 10 years ago, what would it be?

This is a slightly more interesting way of asking about what someone has learned about themselves that they did not know 10 years ago.

How can I be a better partner or friend to you?

None of us are perfect and there is always room for improvement. It takes courage and humility to ask this question. Exercise your own judgement when deciding what you would like to do next, with the answer to this question. Are their expectations of you realistic? Is there any part of what they said that struck a chord with you, that you would like to improve on?

What are your thoughts about seeking help from others when you need it?

Many of us would gladly offer help to our loved ones but are less willing to ask for help when we need it ourselves. If this is the case, what might be some reasons behind the double standard? Perhaps some of us may fear being a “burden” to others, or we might be afraid that seeking help makes us appear weak. On the contrary, it takes great courage to seek professional therapy or ask for support from those around us when we need it.

Some Final Tips

As you start selecting which deep questions to ask your loved one or friend, you might want to keep some of the following tips in mind:

Choose an Appropriate Time and Place

Before you jump into the conversation, consider the other person’s needs at that moment. For instance, take note if the individual you are asking is preoccupied with something else. Are they calm and relaxed, or multi-tasking and completing their work? It also makes a difference if you ask the questions privately, as compared to in front of other people. In a group setting, asking general questions such as how a person’s day went may be more appropriate than deeper questions about conflict resolution, for example.

Consider Starting With Your Own Self-Disclosure

Most of us do not like being interrogated with a long string of questions. It might even remind us of the dynamic between a teacher and student or a police officer and suspect. To even out the power differential, consider sharing some of your own answers before diving into your pool of deep questions to ask. You may also increase the level of safety by adding at the start that they always have the option of skipping any questions that they do not wish to answer. Basically, respecting the other person’s autonomy and creating a safe space to share is key.

Pick Questions That Are Relevant to the Situation

It might seem obvious, but this list of deep questions to ask someone is not a one-size-fits-all list. It can be helpful to start from a place of genuine curiosity. For instance, what would you like to know about the most? Feel free to use some of these questions as conversation starters and add on as the discussion unfolds. Likewise, you might want to hold off on asking all your questions in one go.

Be Mindful of How the Other Person Might Be Feeling

As you go along, take note of both what they are saying, as well as their body language. Are the questions making them appear uncomfortable, withdrawn, defensive, engaged, amused, or something else? You can also check in with them as the conversation goes, by asking them about their experience of the questions thus far.

Deep Questions to Ask your friend

Listen to What the Other Person Has to Say

At times, this might mean that they do not wish to answer any questions at all, and that is their choice. We can either respect their decision, or gently ask if there is anything that we can do to make them feel more comfortable. If they do decide to answer the questions, however, give them the time and space to share. Try to avoid poor listening habits. For example, listen to what they have to say instead of thinking about what you would like to ask next.

Conclusion: Deep Questions to Ask to Truly Get to Know Someone

There you have it – the many types of deep questions to ask to get to know someone better. These may be about their dreams, hopes, struggles, coping mechanisms, memories, relationships, thoughts about life, and so on. Conversations may be about the past, present, or future. Ultimately, selecting questions that are relevant to your situation, coupled with a sense of genuine curiosity and your own honest self-disclosure, may pave the way for more meaningful conversations. Which question would you start with? All the best!