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101 deep questions to take your relationship to the next level

Learn more about people – or even yourself – through these queries for friends, couples or anyone you'd like to get to know just a little bit better.

Asking meaningful questions can be key to living a connected life.

When you ask others – even yourself – questions that delve beneath the surface, it can allow you to go beyond comfort zones and pleasantries to uncover deeper feelings and gain a better understanding of who someone is.

“Being a good listener and question-asker can improve communication skills, help you better engage with others, promote empathetic understanding and, ultimately, build better relationships,” Kimmy Wu, licensed psychotherapist, tells

Asking questions can also help dispel any preconceived notions you may have unknowingly developed, whether it be a friendship or any other relationship.

“Sometimes we make ‘lazy assumptions’ if we have known a person for a long time,” Geremy Keeton, LMFT and senior director of the counseling services department of Focus on the Family, tells

“In life, marriage and extended-family relationships, don’t give up on curiosity and care about another person’s inner life experience just because you think you know them already.”

Gaining insight into how someone thinks or feels can also be beneficial to your career.

“In the workplace, asking and answering deep questions can help you create and contribute to a more open and honest culture, where people are less fearful of sharing their thoughts and feelings,” says Wu, Director of the Asian Mental Health Collective’s WAVES, an initiative that aims to provide a supportive and safe space in the Asian community for discussions about mental health.

Ultimately, the ability to ask meaningful questions is a skill that can not only enhance the quality of your interactions with those around you, but life overall.

With the help of Wu and Keeton, here’s a list of deep questions to help take your relationships to the next level of authenticity.

  • If you were granted three wishes, what would they be and why?
  • What are three adjectives that best describe you?
  • What activities energize you? Drain you?
  • What helps you make difficult decisions?
  • If you could change one thing about yourself what would it be and why?
  • What’s a stressful life event you lived through and how did you handle it?
  • What qualities make you unique?
  • Who have been your greatest influences and why?
  • What are you learning to do right now? What's making that process challenging? What's supporting it?
  • What defines your identity?
  • What are you most grateful for in life?
  • What helps you deal with anxiety or stress? 
  • In what area or areas of your life do you compare yourself to others? How does that affect your wellbeing?
  • What is something you're looking forward to? Why?
  • When do you feel the most confident and why?
  • What quote or piece of advice has impacted you most?
  • What's your favorite song lyric and why?
  • What’s the last thing or person you grieved?
  • What's one thing you are deeply passionate about?
  • How do you learn best?
  • What’s your love language?
  • When do you feel the most loved? Least?
  • What traditions are most important to you?
  • What questions do you have about your heritage or ancestry?
  • How do you handle conflict? Are you more prone to flight, fight or freeze?
  • What are your thoughts on therapy?
  • What childhood trauma have you had to process as an adult? How did you deal with it?
  • When are you most productive? Least?
  • What habit or habits prevent you from accomplishing things you want to do?
  • What toxic thoughts steal your peace, stir up anxiety or assault your confidence?
  • What affirmation helps keep you grounded?
  • What do you believe happens after you die?
  • What role does faith play in your life?
  • What do you think is the meaning of life?
  • Do you think you have a "purpose?" If so, what is it?
  • Is there anything preventing you from fully fulfilling your life’s purpose? If so, what is it?
  • What societal or systemic issue fires you up?
  • What social injustice or inequality is most important to you? What do you wish could be done to change it? How can you contribute to that effort?
  • Are you easily distracted? If yes, what do you do to address those distractions?
  • How do you define personal and professional success respectively?
  • In what areas of your life do you have high expectations? In what area of your life do you accept “good enough”?
  • Who can you count on to give you honest feedback?
  •  What area of your life you could use a coach or mentor for?
  • What do you tell yourself when you make a mistake or something doesn’t go as planned?
  • What do you say to yourself to silent your inner critic? Or do you listen to it?
  • Do you ask for help when you need it? If not, why?
  • Is there a truth, conversation or undertaking you've been avoiding? What is it and stops you from taking action?
  • How would the people closest to you describe you?
  • What type of compliment is most difficult to receive? Why?
  • What chapter of your story do you wish you could rewrite?
  • What do you consider your core values?
  • What areas of your life do you wish you were more efficient in?
  • What motivates you to give your best effort?
  • Do you consider yourself an extrovert, introvert or ambivert?
  • What was a dark time in your life? Looking back, what can you learn from that period?
  • What activity or activities bring you joy?
  • What memory or experience brings you back to your childhood?
  • What have you always wanted to try, but haven't because you think it’s too expensive, too hard, too late or other roadblock?
  •  What are relationship non-negotiables or deal breakers?
  • What does it mean to you to have chemistry with someone?
  • If you could write your own legacy, what would it say?
  • What's something you wish you had more time for?
  • What is something you're irrationally afraid of?
  • Has a phobia ever prevented you from doing something important to you?
  • Do you have a rhythm, routine or system in your life that really works?
  • In what aspect of your life do you wish you had more freedom and why?
  • What gives you a sense of belonging?
  • What do you wish you were better at?
  • What's one thing you've done that you're proud to tell people about?
  • Do you feel like you're taking care of yourself physically, emotionally and/or mentally? If not, why not?
  • What boundaries do you wish you could put in place to live a happier life?
  • What worries you most about the future? What gives you hope?
  • When was the last time you did something out of your comfort zone? What was it?
  • What impact does the opinion of others have on you? Whose opinion do you care about the most?
  • What or who couldn’t you imagine living without? Why?
  • How do you support others who are having a tough time?
  • What do you wish you could say “no” to more often? What do you wish you could say “yes” to more often?
  • In what types of situations do you tend to overreact?
  • Has there ever been a time that you haven't been able to forgive someone? Do you ever imagine a time that you'll reconcile?
  • What’s the best gift you’ve ever received from someone else? What the best gift you've ever given?
  • Have you ever pretended to be someone or something you’re not?
  • What does "living an authentic life" mean to you?
  • How can you learn to embrace your imperfections?
  • What leaves you awestruck?
  • Do you like yourself?
  • How do you define self-love and self-worth?
  • How do you process difficult emotions and when you're experiencing them, do you reach out to others for support?
  • If your life was a book, what would the current chapter be called? Why?
  • Is there someone or something you feel you need to apologize to and for? Why?
  • If you were given the opportunity to see the future, would you take it? Why or why not?
  • If a past version of yourself saw your present life, what would they think?
  • What’s a desire that you rarely tell others, but wish they could know?
  • Do you have a secret that you feel you can never share?
  • Who or what has had the most impact on who you are right now?
  • What do you consider most beautiful in this world? Horrible?
  • If you won the lottery, what's the first thing you'd do with the money and why?
  • How do you define or describe “a good day”?
  • What would you do if you had a week to do anything you wanted?
  • If you could see the future, what would you be doing differently a year from now? The same?
  • Ten years from now, what do you hope to be doing?
  • Who do you know that cares for you most in this world and how do you know that? And, who are the people you most care about and why?