Asking deep questions can be important for building strong, meaningful relationships. Research has shown that engaging in more intimate conversations increases feelings of closeness and emotional connection between individuals.
One study published in the Journal of Social and Personal Relationships found that self-disclosure, or revealing personal information about oneself, was positively associated with feelings of closeness in romantic relationships (Collins & Miller, 1994). Another study published in the same journal found that asking and answering personal questions was associated with greater feelings of intimacy and closeness in both romantic and non-romantic relationships (Aron et al., 1997).
Furthermore, a study published in the Journal of Experimental Psychology found that asking questions and showing genuine interest in another person can increase feelings of liking and attraction towards them (Aron et al., 2004).
Asking deep questions is an effective way to increase intimacy and emotional connection in relationships, and it also helps to build attraction and liking toward another person.
Contents
Deep Questions You Can Ask Anyone
- What has always been on your bucket list but never had the chance?
- What is your biggest fear in life?
- If you could live anywhere, where would it be and why?
- What was the most challenging decision that you ever had to make and what do you regret most?
- What would you change about yourself if you could?
- What belief do you hold that most people would disagree with?
- What is the 1 thing you cannot survive without?
- If you could go back in time and alter 1 thing, what would it be?
- What is your most treasured memory?
- Do you believe in fate or free will?
- How would you define love?
- What makes for a perfect day for you?
- What is your greatest accomplishment any person has done, living or dead, and why?
- What has been the most valuable lesson learned throughout life so far?
- If you could possess any superpower, which would it be and why?
- What 1 thing do you wish people knew about you that no one else knows?
- What question would you ask if you could ask any person in the world, and who would it be?
- What’s a subject you have always wanted to learn but haven’t had the chance?
- What do you believe happens after we pass away?
- What negative beliefs about yourself do you wish to alter?
- What book or movie would you select if you could trade places?
- What’s 1 goal you have set for yourself that you are working towards right now?
- What have you learned from a challenging experience that made you stronger?
- What’s 1 thing you are proud of but haven’t told anybody yet?
- And most importantly, what passion do you have?
- What moment would you wish to relive and why?
- What’s 1 goal you hope to accomplish before death?
- What are you grateful for right now?
- What advice would you give your younger self?
- What three people would you invite for dinner and why?
- What’s something on your bucket list that you have been hesitant to attempt?
- What’s 1 thing people should better understand about you – one pet peeve or something?
- Whomever it may be, it would make for an interesting evening together!
- Which time period would you select to live in and why?
- What’s 1 question you have always wanted to ask your parents but haven’t?
- What would be your lasting memory of you if only one memory were kept?
- If only 1 memory were kept, which one would it be?
- What’s 1 thing that always lifts your spirits when you’re feeling down?
- What has always piqued your interest about the world?
- If you could change 1 thing about yourself, what would it be?
- What advice do you wish someone had given you when younger?
- What would you change if no one judged you?
- What have you always wanted to say but never said?
- What interests you but doesn’t quite feel confident?
- Are there any topics on which you feel informed but lack understanding?
- If you could spend 1 day with any person, who would it be and what would you do?
- What do you hope to accomplish in your career?
- If you could switch lives with any person for a day, who would it be and why?
- What would be 1 thing you would like to learn or explore further in the future?
Questions To Ask Your Boyfriend
- What are your biggest fears?
- What goals and aspirations have you set for yourself?
- What do you believe to be your purpose in life?
- Is there 1 thing about yourself that you wish could change about yourself?
- Where would you go if you could travel anywhere, and why?
- What’s most important in your life right now?
- What have you always wanted to try but never had a chance to?
- If you could change 1 thing about this world, what would it be?
- What’s your biggest regret?
- How do you define success for yourself?
- What has been your greatest passion since childhood?
- What has been the most challenging experience you have had to go through?
- What was the happiest moment of your life?
- What’s something you can’t imagine living without?
- What has been the best gift you have ever received?
- What would you choose as your ideal historical figure, and why?
- What’s 1 thing on your bucket list before death?
- How do you cope with stress?
- What have you learned throughout life that has shaped who you are today?
- Finally, what’s 1 pet peeve of yours?
- In your opinion what is the most essential element in a relationship?
- What have you learned from past relationships that have made the biggest impact on you?
- If you had a choice between love and money, which one would you pick and why?
- Is there anything on your mind that you have wanted to tell me but never had the chance?
- How can we strengthen our bond as friends/partners?
- What’s your ideal day?
- What has been the most positive thing that’s happened to you this year?
- What cause are you passionate about?
- What moment in your life would you relive and why?
- What’s 1 thing that you wish to improve about yourself?
- What has been your greatest achievement?
- What issue are you currently struggling with?
- How do you handle disappointment?
- What do you believe people misunderstand about you?
- What superpower would you choose and why?
- What’s the most valuable lesson learned from a family member?
- What would you change about society if you could?
- How do you deal with failure?
- What are you most excited about in the future?
- What has been the most profound realization you have ever had?
- What passion do you have that others might find strange or eccentric?
- Most importantly, what’s been the most valuable lesson learned about love?
- What’s 1 task you have been putting off that you know you should do?
- What would you most want your future children to learn from you if any?
- If there was 1 talent you wished for but don’t currently possess, what would it be and why?
- What has been your most influential learning experience from a friend?
- What do you find most curious that you haven’t explored yet?
- What has been the toughest decision you have ever made so far?
- What are you most thankful for?
- How would you like to be remembered?
Questions To Ask Your Girlfriend
- What are your biggest fears and how have you conquered them?
- What do you believe is the meaning or purpose of life?
- What are your greatest strengths and weaknesses?
- Most importantly, what truly brings out the happiness in you?
- What would you change about yourself if you could?
- How do you handle difficult situations and challenges, and how has that shaped you?
- What defines true love to you?
- What would make the perfect day perfect for you?
- What is your one goal in life?
- What’s been the most valuable lesson you have learned so far?
- What’s your biggest dream and how are you working towards achieving it?
- What makes a relationship feel loving to you?
- What qualities make someone special to you?
- What do you desire most from me that you don’t currently have access to?
- How can we deepen our connection as partners?
- What has been the most significant decision you have made and how did it shape who you are today?
- What drives you the most passionately?
- What is the 1 thing you wish to learn or explore more about?
- What has been your greatest regret, and what have you learned from it?
- What has been the most profound realization you have ever had?
- What have you discovered about yourself through our relationship that is most valuable?
- What has been the most meaningful gift you have ever received?
- What do you look forward to in the future?
- What would you change about our world if you had a chance to change it?
- What has been your biggest accomplishment thus far?
- How would you define success in relationships?
- What would you do if you weren’t afraid?
- What would be your ideal vacation?
- What lesson do you want to instill in our future children’s minds about our relationship?
- What do you cherish most about it now?
- What has been the most challenging obstacle you have overcome in our relationship?
- What have you learned from past relationships that you think is most valuable?
- What wisdom have you gleaned from family members or close friends?
- What quality does a successful partner possess that you value most?
- And finally, what’s your biggest pet peeve?
- What do you find most intriguing about yourself that you haven’t explored yet?
- What has been the most important lesson learned about forgiveness since we’ve been together?
- How could you improve yourself as a partner to make yourself even better?
- What has changed most since we’ve started dating?
- What is your biggest worry or concern about our relationship?
- What do you find most grateful for each day?
- What has been the most helpful lesson learned about communication in a relationship?
- Finally, how do you take care of yourself?
- What do you need from me to feel supported and understood?
- What has been putting off that you know you need to get done?
- What does your ideal home and family life look like for you?
- What 1 thing have you always wanted to share with me but are afraid to do so?
- What do you believe people misunderstand about you?
- What has been the biggest change in me since we’ve been together?
- What would it take for you to truly love and appreciate me?
Questions To Ask A Guy
- What’s the happiest time you have ever spent with a friend?
- What qualities do you look for in a partner?
- How satisfied are you with your current job/career?
- Is there anything on your bucket list that you just can’t seem to make happen yet?
- Name 1 change you change if you could go back in time and alter one thing?
- What do you believe to be the most essential quality in friendship?
- How do you handle difficult situations or conflicts with others?
- What do you believe to be the purpose of life?
- Have you ever experienced heartbreak? How did you cope with it?
- What topic are you passionate about?
- Which book was the best one you have ever read and why did you enjoy it so much?
- Do people truly change or are they set in their ways?
- What has been the greatest challenge you have overcome thus far in life?
- If you could choose any job, what would it be?
- What accomplishment are you most proud of but rarely share with others?
- How do you cope with stress?
- What would you wish more people knew about you?
- If you can meet any person who would it be, living or dead?
- What’s your favorite activity when you have free time?
- What one thing would you change about yourself if given the chance?
- Do you believe that everything happens for a reason?
- What’s the best advice anyone has ever given you?
- What have you always wanted to try but never had the courage to do?
- What’s one thing you do every day that brings joy into your life?
- How would you define success?
- And what fear are you most afraid of?
- What three words best describe you?
- Recently, what have you discovered about yourself? Do you believe in love at first sight?
- Have there been any decisions made that you are regretting?
- What has been your greatest regret thus far?
- How do you feel about your relationship with your family?
- What’s something that no one knows about you that would surprise them?
- If you could travel anywhere, where would you go?
- What skill set are you particularly good at?
- Do you believe it’s possible for people to find their soulmate?
- What have you gained from past relationships?
- If you could possess any superpower, what would it be and why?
- What struggles are you currently dealing with?
- What accomplishment are you most proud of?
- How would your friends describe you if they met you for the first time?
- What goals do you hope to accomplish this year?
- How do you feel about yourself right now?
- What one thing are you working on improving about yourself, and what are you most grateful for?
- What would you say if you could have a conversation with your younger self, and what would it include?
- What are you most looking forward to in the future?
- How do you handle failure?
- What accomplishment do you hope to be remembered for in the future?
- What’s one question you wish someone would ask you?
Questions To Ask A Girl
- What have you always wanted to try but never had the chance?
- If you could change one thing about the world, what would it be?
- What are your biggest fears and how do you manage them?
- What qualities do you believe are most important in a person?
- What makes for a successful relationship?
- What defines happiness to you?
- What advice would you give yourself if you could go back in time and give to yourself when you were younger?
- What do you believe the meaning of life to be?
- What has always been on your bucket list but never got around to trying?
- If you could have dinner with anybody who would it be and why?
- What has been your greatest accomplishment and why?
- What has been your most important lesson learned so far in life?
- What have you always wanted to learn but never had the chance?
- If you could stay anywhere, where would it be and why?
- How would you define success for yourself and why does it matter so much to you?
- What do you consider to be worthy of fighting for in a friendship or romantic relationship?
- If you could go on any kind of road trip anywhere, where would it be and why?
- What do you believe the essence of true happiness to be?
- If you could alter one aspect of yourself, what would it be?
- What has been your biggest risk ever taken?
- What do people often misunderstand about you?
- What do you find to be your passion and why?
- What do you believe to be the key to a long-lasting and fulfilling life?
- What has been the most valuable lesson about yourself that you have learned over time?
- What is something you have always wanted to try but haven’t had the courage yet?
- What do you consider to be the most essential quality in a partner?
- What makes you feel truly alive?
- What has been your most significant lesson learned from past relationships?
- What has been someone’s most meaningful act ever done for you?
- What quality do you consider most essential in a friend?
- What quality would you most value in a family member?
- If you could alter one thing about the world, what would it be and why?
- What are your opinions on spirituality or religion?
- What do you consider to be the most valuable lesson your parents taught you?
- What has been something in your life that you are thankful for?
- What advice would you offer others when facing hardship?
- What do you believe is essential to living a joyful and satisfying life?
- What do you feel is the most significant lesson you’ve learned about love?
- What would you wish more people knew about you?
- What has been your biggest takeaway when it comes to forgiveness?
- Moreover, what has been your most crucial takeaway when it comes to resilience?
- What are you currently struggling with and why?
- What accomplishment are you proud of and why?
- What quality would make a good mentor or role model?
- What has been your most valuable lesson in communication so far?
- What have you always wanted to share with someone?
The sources of the research cited in this response are:
Collins, N. L., & Miller, L. C. (1994). Self-disclosure and liking: A meta-analytic review. Psychological Bulletin, 116(3), 457–475. https://doi.org/10.1037/0033-2909.116.3.457
Aron, A., Melinat, E., Aron, E. N., Vallone, R. D., & Bator, R. J. (1997). The experimental generation of interpersonal closeness: A procedure and some preliminary findings. Journal of Personality and Social Psychology, 73(1), 33–48. https://doi.org/10.1037/0022-3514.73.1.33
Aron, A., Dutton, D. G., Aron, E. N., & Iverson, A. (2004). Shared activities and marital satisfaction: Causal direction and self-expansion versus boredom. Journal of Social and Personal Relationships, 21(2), 247–262. https://doi.org/10.1177/0265407504041379
I’m Kary Walters, a couples mediator, life coach, and writer with a passion for helping couples stay together and achieve their relationship goals. With over a decade of experience, I specialize in self-improvement and have worked with individuals & couples facing challenges.