29 Of The Most Interesting Questions To Ask People To Draw Them Out

Do you ever have trouble connecting with people and engaging with them on a deeper level? 

One of the best ways to draw someone out and get to know them is by asking interesting questions.

Asking the right questions can stimulate more exciting and fun conversations.

It can set the stage for discovering common interests, developing a more authentic connection, and fostering mutual empathy and understanding.

29 Interesting Questions to Ask People to Get to Know Someone

By asking these questions to get to know people, you are revealing something about yourself as well. You are showing others that you are engaged, interested, and aware of their value as a person.

You are inviting authentic and genuine sharing and connection. When you make others feel valued and important, you set a foundation for a lasting, mutually satisfying relationship.

1. What is your best childhood memory?

This fun question always makes people smile and often leads to a humorous or poignant exchange about family, travel, holidays and traditions, hopes and dreams, and friendship.

You learn a lot about someone when they share aspects of their childhood.

group talking, questions to ask people

2. If you had a chance for a “do-over” in life, what would you do differently?

Good interesting questions that give you insight into a person's state of mind about who they are, their vulnerabilities, and their hopes and dreams create deep conversations.

Often sharing regrets or unmet desires opens doors to considering new possibilities or the confidence to make a needed change.

3. How did the two of you meet?

This is a personal question to ask people who are dating or married. Quite often sharing the story of how they met draws them together in a mutual happy memory.

It gives them a reason to reconnect and allows you to learn more about their past and how they interact together as a couple.

4. What do you feel most proud of?

This is one of the best questions to ask to make people feel you are really interested in them and who they are.

Everyone wants to feel accomplished and proud, and we all want an opportunity to share our successes without looking like a braggart.

The answers give you great insight into what the person values most in life.

5. What is your favorite music?

The music we enjoy helps define us and reflects the dreams and attitudes of our generation.

What we listen to reflects what speaks to our souls. It reveals who we are and what we believe — in an illuminating and honest way that's often hard to put into words.

6. If you could travel anywhere, where would you go and why?

This question not only allows you to discuss and share travel experiences, but also it affords insights into the other person's interests, personality, and sense of adventure.

7. If you could only keep five possessions, what would they be?

This personal question really makes people think. We are so attached to our possessions, but truthfully there are only a few that matter deeply to us. When people are forced to define those few, it gives insight into what they value most.

8. What teacher in school made the most impact on you and why?

Teachers can play a pivotal role in helping us develop a love of learning, discover our life passions, and draw out our innate skills.

Sometimes they are people who inspire us or who simply believe in us and want the best for us.

9. What do you want your tombstone to say?

Although this is a morbid question, it does go right to the heart of what we want for ourselves.

father and son, questions to ask people

At the end of our lives, how do we want to be remembered and what legacy do we want to leave?

10. What was one of your most defining moments in life?

This is a great question to invite sharing on a deeper and more vulnerable level.

Often defining moments come during profound life transitions like death, divorce, job loss, etc.

It is during these times we are called to make a huge mental, physical, or emotional shift.

11. Why did you choose your profession?

The story of how someone landed in a particular profession opens the door to learning a lot about a person and their motivations, interests, education, and ambitions.

We spend most of our days working, so the answer to this question also reveals how a person chooses to define their lives.

12. How do you spend your free time?

This is a great follow-up question to the previous question.

It rounds out the picture of how this person has created his or her life and what hobbies, interests, and obligations they have created for themselves.

13. If you won the lottery, what would you do?

This is a fun question that reveals so much about a person and their attitudes about money, work, and life passion.

Would they leave their job? Buy their dream home? Do something altruistic? Would they be happy about having a lot of money or want to avoid it?

14. Who do you most admire in life?

This is an interesting question to learn more about the kind of person someone wants to emulate. We admire people whose actions and character reflect what we want in ourselves. This will tell you a lot about the true character of a person.

15. What are your top three favorite books and why?

Sharing favorite books opens the door for interesting conversation and finding common ground between you.

It gives you and the other person a chance to learn something new and potentially to understand a new perspective or interest you haven't pursued.

16. What are you most afraid of?

This is a very probing and enlightening query. Everyone has fears, and our fears reveal our vulnerabilities and pain.

When someone shares this with you, you must respond with care, kindness, and trustworthiness. You must treat their fears with dignity so they feel safe connecting with you on this more intimate level.

17. What feels like love to you?

Everyone has their own “love language” — the words, behaviors, and attitudes that make them feel loved and that reveal how they express love.

This is a great question to ask your spouse, romantic partner, or a potential romantic partner.

18. What is your strongest quality?

Many people feel uncomfortable with intimate questions at first because they want to appear modest.

But truly we all want to feel validated about our positive qualities and have others recognize this about us.

People will usually follow up by asking this question of you, and it creates a positive feeling and bond between you.

This inquiry is one of the best to ask to really get the conversation going and make a good interaction.

19. What was your most embarrassing moment?

This is one of those fun questions that can lead to laughter and connection.

Most people enjoy telling funny stories about themselves if there isn't shame or guilt involved.

Occasionally someone will reveal something painful or shameful, and this is the time to show empathy and caring.

20. If you were president, what is the first thing you would do?

You can learn a lot about someone's political beliefs, ideals, worries, and values when you ask this question.

If you want to connect and invite open discussion, just be sure you don't challenge or put down the response you get if it happens to be different from what you would do.

21. What age do you feel right now and why?

This is one of the random things to ask someone over 50. You will get some interesting responses.

As we get older, most people don't “feel” their chronological age. It's enlightening to learn how people perceive themselves internally even though externally they may be at a completely different stage of life.

22. If you could witness any event of the past, present, or future, what would it be?

This is a very interesting question that invites a fascinating discussion.

You can learn about someone's interests and goals, and perhaps you'll be inspired to delve into a new interest yourself.

23. What is a skill you'd like to learn and why?

Most of us have something we want to learn to improve ourselves or for simple enjoyment.

This interesting question gives the person the opportunity not only to share that desire but also to examine why they haven't pursued learning the skill.

24. What does a perfect day look like to you?

Thinking about this question requires us to dig around in our memories for previous perfect days.

It's a feel-good inquiry that gives both people an infusion of happiness and maybe even the desire to recreate that perfect day.

25. How would your friends describe you?

Asking this allows the other person to talk about themselves from an outside perspective. It invites self-awareness and self-honesty and opens the door to a more authentic conversation.

26. What or who really cracks you up and why?

Shared humor can be the foundation for a great relationship. This question can lead to a fun conversation about comedians, friends, movies, and any number of topics that you both find funny.

27. What are your top five life values?

The values you cherish the most reflect who you are, what's most important to you, and where and how you spend your time.

It's good to notice if someone mentions a value that they don't reflect in the way they live or the choices they make.

28. Who are the three people you spend the most time with?

They say we're a reflection of the people we spend the most time with. Knowing who someone hangs with most often can tell you a lot about this person.

Follow up the question by asking for a description of these people and why they are so important.

29. Do you view the world as more good than bad or bad than good?

This question is similar to asking if someone is an optimist or pessimist. But it also goes to the heart of how they view society and our culture as a whole.

You can be a pessimist and still believe the world and people are essentially good. Does this person's worldview align with yours?

More Related Articles:

How To Start a Conversation When You First Meet Someone

101 Of The Best Funny Get To Know You Questions

Why Questions Are So Powerful

By learning good questions to ask people and taking the time and interest to keenly listen, you are setting the stage for more intimate, fulfilling, and enjoyable relationships.

  • Asking interesting, open-ended questions reflects your genuine interest in people and shows you are a reflective and caring person yourself.
  • It also improves your communication skills as you practice different questions and adapt questions to each situation.
  • You can also make other people who are socially uncomfortable more comfortable by drawing them out with the right question. This helps build trust in the conversation and in a relationship.
  • Questioning others also increases your understanding of others and improves your knowledge, as there is something new to learn from everyone.

Take the time to prepare some questions for your conversation toolbox, so when the moment is right, you'll have an intriguing question on the tip of your tongue.

The Art of Asking Interesting Questions

There is an art to asking interesting questions and creating an engaging conversation.

No one wants to feel as though they're in a job interview or being grilled for information, especially in a social setting.

But asking appropriate and open-ended interesting questions, mixed with some of your own comments and observations, is the formula for lively conversation.

An interesting conversation involves these skills:

  • Show interest in the other person (or people) and reflect genuine curiosity in them with your questions.
  • After asking someone about themselves it's important to listen mindfully to their reply in order to hear beyond the words spoken.
  • Mindful listening requires watching body language, listening to tone of voice, and being sensitive to what is left unspoken.
  • Follow-up thoughtfully with great questions or make reflective or supportive statements.
  • Be sure there's a balance of give and take in a conversation so that one person isn't doing all of the talking.
  • Prepare yourself with topics of interest and fun questions.
  • Try to be yourself. You don't need to pretend or show off to be a great conversationalist.

Do you feel more confident with these questions to ask people?

Now that you know how powerful this strategy can be, hopefully, you'll take advantage of it the next time you meet someone new

Whether it's a potential romantic partner, a business associate, or someone who might become a friend, using interesting questions shows that you care enough to learn more about the person. 

Try to choose questions that are appropriate for the person with whom you're engaging.

Show interest in the answers, ask follow-up questions, and be open enough to answer any questions that come your way. 

The more you get to know a new person, the more commonalities you'll find that you can build upon to create a long-lasting relationship.

20 thoughts on “29 Of The Most Interesting Questions To Ask People To Draw Them Out”

  1. Thank you for your thoughts on this. Many people are totally stumped with how to initiate or maintain conversations and I believe (this is totally unscientific) that we are getting worse at this as we increasingly go to social media for our interactions.

  2. This is a great list of questions to ask people! #19 about embarrassing moments is one of my favorites. When 2 people feel comfortable enough to share a vulnerable fact or story good conversation usually follows.

  3. Its very informational way to learn about people around you. Many relationships,friendships are so common that you get easily bored.Its because we forget or dont look the detail of that person’s personality.So this questions might help a little.Thank you for sharing.

    • Do you have any scars and how did you get them? That always seems to start an entertaining conversation.

      These questions would work as journal prompts also.

  4. I learned very early to avoid the typical dinner and a movie as a first date in favor of dinner and a stroll. It would give an opportunity to present some of those same questions and better know if a second date was worthwhile.

  5. don’t ask people the tombstone question unless you know they have not recently experienced a death in their family.
    This is a good list of things to ask younger people. A lot of these questions should not be asked of older people

  6. As reading these 25 questions, I’d really love to answer.
    I’m sure some of those will be asked by the people who truly care about you – without reading this article, because they are genuinely interested in you.
    Thank you for sharing.

  7. I would not agree with this list at all. If someone asked me these very personal questions I would be less likely to share my feelings with them on anything. No one but a close friend or loved one should feel a need to ask questions like these.

  8. Thanks for sharing. I feel these questions are pertanent and make it easy for individuals to learn significant elements of the other personality. Some of these questions can be used at a small dinner party too.

  9. Thanks for these brilliant questions. These can be asked in non-formal based relationships but in office settings these questions might look awkward.
    please post some of these.

  10. If you just met the person some of these questions might be hard to ask as its kind of embarrassing but some are completely fine , The person might be on edge but how they say there answer says a lot about there personality so keep an eye out for that .. – its not what they say but its how they say it –


  11. The reason why I read all the question is because I want to improve my english. It helped a lot. While reading the questions, I was pretending that someone was asking me and I had to answer all of it. I know it sounds weird,but it really helps me a lot.

    Thank you so much!

    Trishia Combes

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