25 Of The Best Questions To Ask People To Draw Them Out

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As a life coach, I use pointed and interesting questions to help my clients gain more clarity about themselves and to help me better understand my clients and their goals.

I generally used my list of questions that can't be answered with a simple “yes” or “no” so that the client is encouraged to dig deeper and uncover answers they may not have realized previously.

Often after I would ask a unique question, a client will say, “I've never thought about that before.” Once they ponder the question and their feelings about it, it can lead to a profound insight or an “ah ha” moment.

Even in social or casual settings, asking the right questions can stimulate deeper and more interesting conversations.

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

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

The Art of Conversation Explained

No one wants to feel as though they're in a job interview or being grilled for information, especially at a social setting. But asking appropriate and open-ended questions, mixed with some of your own comments and observations, is the formula for lively conversation.

group talking, questions to ask people

When you are in a social setting, remember that an artful conversation involves these skills:

  • Show interest in the other person (or people) and reflect genuine curiosity in them with your questions.
  • After asking good questions 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 great questions (see below).
  • Try to be yourself. You don't need to pretend or show off to be a great conversationalist.

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 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.

Here's a list of 25 questions to ask people to really get to know them:

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.

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

Good 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.

Read Related: 15 Great Conversation Starters To Connect With Anyone

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.

Simple Self-Confidence

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. 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 that 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.

father and son, questions to ask people

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 a great 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 question. 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 personal quality?

Many people feel uncomfortable with personal 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 is one of the best questions to ask to really get the conversation and make a good connection.

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 questions 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 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 question 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?

This question 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.

The best 25 questions to ask people to really get to know them. Click To Tweet

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 are setting a foundation for a lasting, mutually satisfying relationship.

Did you find any value from these get to know you questions?

I hope you enjoyed my list of questions to ask people.  Which ones were the best questions to ask your friends and neighbors?

Would you like to share with others?

It would be really great if you could help me spread these great conversation starters. Would you be willing to share this list of questions article on your preferred social media platform?

photo credit: Jim Blob Blann

Click Here to Leave a Comment Below 23 comments
  • holly

    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.


      thats my birthday

  • Ron Clendenin

    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.

  • Friday’s Fresh Five! (10/24/14) | What about this?

    […] “What does a perfect day look like to you?” I could easily answer question #24 of 25 Questions to Ask People, but I would have to stop and ponder my answers to some of the other questions. Whether you ask […]


      some of those questions can not be asked directly as they embarrassing but you can get the answers during the time if the relationship is serious.
      most of friends does not know details about each other even some time they don’t know the family name of the friend.
      I think those questions are important for marriage project to understand spouse personality.

      thank you for sharing your knowledge.

  • İrma

    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.

  • Les.B.

    Good questions to ask ones self


      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.

  • FredZilch

    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.

  • Lynn

    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

  • Dankha

    Hello ! great post . get a a lot of things to make strong relations and some other things to groom personality . looking for more info. thnx

  • Le Ngoc Ngan

    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.

  • Mindfulness Exercises

    […] distract yourself with your phone, computer, or the other people around you. For the time you are interacting with them, the other person should have your full […]

  • Dhayanithi

    Great Thoughts! Thanks for sharing! You enrich me! I’m indebted to you!

    Dhayanithi, Coimbatore, Tamil Nadu, India

  • Kaitlyn

    This helped me thank u

  • Cassie

    omg thx

  • tiffany267

    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.

  • Vicky

    helped me in my math project☺☻♥

  • Lynette

    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.

  • anuja

    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.

  • Eman

    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 –


  • Patricia Bea Combes

    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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