Good questions are powerful. They force answers.
Deep and compelling questions force us to think profoundly and examine ourselves and learn more about the people we want to know better.
Are you trying to know someone, but you’re at a loss for the right questions to ask?
Or maybe you want to explore your own inner world through questioning to evolve to a new level of happiness, self-confidence, and inner peace.
Good deep questions are more personal questions that go beyond favorite colors and whether or not pineapple tastes good on pizza.
They go to the heart.
Let’s look at some questions to ask others and yourself.
Deep Questions to Ask a Guy
Here are some serious questions to ask a guy you’re getting to know. If some strike him as too personal, you can always offer to go first in answering the question.
1. How would you describe the “perfect life”?
2. Do you think God is real — and why (or why not)?
3. What would you do if your date cooked for you and then started to clean up after the meal?
4. Do you think a woman is ever asking to be treated like a sex object?
5. What is your take on feminism?
6. What is the weirdest thing you’ve ever done?
7. What’s the most embarrassing thing you’ve ever done for someone?
8. Would you rather be a gifted musician, mathematician, or storyteller?
9. What is something you really like about yourself?
10. What do you wish more people knew about you?
11. How would you rank the following in importance: family, career, love life, spiritual life?
12. If you married, would you expect to be recognized as the head of the family?
13. Do you expect your spouse or partner to vote the same way you do?
14. Would you describe anyone as evil, and why?
15. What should all people be taught to do for our planet?
16. Would you lay down your life to save someone else?
17. What would you do for a career if you never had to worry about money?
18. What three items would you want with you on a deserted island?
19. If you could live anywhere in the world, where would you live?
20. Do you believe everyone has a soul mate – or even more than one?
21. If you had one month left to live, how would you spend it?
22. What would a perfect day for you look like?
23. Where do you want to see yourself three years from now?
24. If you died today, would you be satisfied with the life you’ve lived?
25. What movie influenced you the most?
26. Would you rather be a world-famous athlete or the leader of a country? Why?
27. Can you remember the last time you cried? And what was the reason?
28. If you had to live with one of your family members, who would it be, and why?
29. If you had to spend a million dollars in three days, how would you spend it?
30. If someone made a movie about your life, which actor would play you?
31. What ability of yours are you most proud of?
32. Who is your favorite superhero, and why?
33. Would you rather be extraordinary and unknown or ordinary and famous?
34. Which period of history would you change, if you could, and how?
35. Are you a cat or a dog person, or do you prefer another animal as a pet?
36. Are you a collector — and, if yes, what do you collect and why?
37. Have you ever experienced an identity crisis? If yes, what happened?
38. Do you still feel guilty about a choice you made in the past?
39. What’s one item you’ll cross off your bucket list this year?
40. Who is your real-life hero, and why?
Deep Questions to Ask a Girl
If you’re looking to get to know a girlfriend (platonic or otherwise) better, ask any of the following deep questions.
If she’s as ready to learn more about you, she’ll probably ask you to answer them, too.
1. Would you rather have a partner without a baby or a baby without a partner?
2. What would you say to a guy who suggested you change the way you dress?
3. Have you ever been “mansplained,” and if yes, how did you handle it?
4. Do you consider yourself religious or spiritual (or neither)? And why?
5. Why do you think people fall in love – chemistry or good timing?
6. Have you ever asked a guy out on a date? If yes, why?
7. Have you ever wondered what it would be like to date a woman instead?
8. What book (or audiobook) influenced you the most?
9. Would you stay with a spouse who cheated on you?
10. Do you believe in giving people second chances? Are there times when you don’t?
11. How do you feel about the #MeToo movement?
12. Do you think human beings are harming the planet?
13. What would be a perfect vacation for you?
14. What mythical creature would you like to be, and why?
15. To which member of your family do you feel closest, and why?
16. What are your favorite ways to exercise?
17. Would you rather have ageless beauty or unlimited wealth?
18. What part of your body do you consider attractive?
19. How would you describe your first crush? And how did it end?
20. What do you look for in a relationship?
21. How would you describe a perfect date?
22. What legacy do you want people to remember you for after you’re gone?
23. Would you date someone who was bisexual or biromantic? Why or why not?
24. What life-changing event have you experienced?
25. What do you think is humankind’s greatest invention (or one of them)?
26. Would you rather be telepathic or be able to teleport?
27. If you could choose a superpower, what would it be?
28. What three adjectives would you use to describe yourself?
29. What made you fall in love with your significant other (or a past partner)?
30. What is your take on astrology?
31. Do you think it’s possible to know the future? And would you want to?
32. Have you had your heart broken? What did you learn from it?
33. Have you ever experienced a break-up that made your life better?
34. What was your favorite subject in high school?
35. Have you ever acted on stage — or have you ever wanted to?
36. Do you find it difficult to admit when you’re wrong? Why or why not?
37. Are you attracted more to impractical dreamers or to practical achievers?
38. When you were a kid, what did you want to be when you grew up?
39. Have you ever lost a loved one? And if yes, how has that loss changed you?
40. What’s your take on body positivity?
Deep Questions to Ask Your Friends
Whether you’re looking for questions to ask your significant other or your best platonic friend, the following deep questions can help you both understand each other better than ever.
1. What do you think happens after we die?
2. Do you think magic is evil, a hoax, or a natural extension of our nature?
3. Do you believe in fate? Or do things happen only because of our decisions?
4. Do you believe someone’s DNA says all you need to know about their gender?
5. What was your most memorable birthday, and why?
6. If you had to give up one of your senses, which would it be?
7. What is your biggest pet peeve in the workplace?
8. What is your view on monogamy and “til death do us part”?
9. Have you ever switched political parties. And, if yes, why?
10. How happy are you right now? And what would make you happier?
11. If you could change something about your appearance, what would it be and why?
12. What important lesson have you learned from a friend or family member?
13. If you could make anything to perfection for someone you love, what would it be?
14. Are you afraid of dying? Why or why not?
15. What do you think of your given name?
16. Have you ever had an experience that helped you make a big change?
17. If you could swap places with someone else for a day, would you?
18. How do you cope on those days when everything seems to go wrong?
19. In an intimate relationship, what is your biggest turn-off?
20. In general, do you prefer engaging in or avoiding political discussions?
21. What are your thoughts on traditional male and female roles?
22. Do you like who you are now?
23. If you died today, is there anyone you’d regret not reaching out to?
24. If all your wishes were granted today, what would your life look like?
25. At what age do you think people should get married, and why?
26. When you’re in a bad mood, would you rather have company or be left alone?
27. When it comes to exes, do you prefer to burn bridges or remain friends?
28. Do you believe people of the opposite sex can be platonic best friends?
29. Do you keep a journal, and, if yes, how often do you write in it?
30. Have you ever learned to trust someone again after they betrayed you?
31. What do people constantly misunderstand about you?
32. What one person do you most want to hear from when you’re hurting?
33. Is there someone in your life you haven’t forgiven?
34. When was the last time someone made you feel unique and amazing?
35. How have your political or religious views changed in the past ten years?
Why it’s difficult to ask yourself hard questions
What do you do when the one you’re questioning turns around and asks you a question you find difficult to answer?
Easy as it is to ask these questions of someone else, it’s not easy to ask and answer super deep questions about yourself.
But if you’re going to ask deeply personal questions of others, you should be prepared to reciprocate by answering theirs.
When people are resisting the inner work it requires to explore powerful questions, it could be for one of the following reasons:
- It’s uncomfortable to face certain truthful questions about yourself.
- You fear the necessary changes the questions will provoke.
- You don’t want to experience the possible pain of self-reflection.
- You feel confused about what your next steps should be.
- You worry your new awareness might negatively impact a relationship.
All of these are valid reasons to feel hesitant about exploring your inner world through questioning — but don’t let them sidetrack you from this valuable work.
Right now is the best time to begin this self-exploration! Consider the following deep questions good practice.
60 Deep Questions to Ask Yourself
1. What legacy am I leaving the world after I’m gone?
2. How am I living or behaving inauthentically?
3. What (or who) am I tolerating that I really don’t want in my life?
4. How am I making choices based on “I should” rather than “I desire”?
5. How am I behaving as a reactor rather than an initiator?
6. How am I censoring what I really think or feel because I’m afraid?
7. Where do I have a “lack” mentality?
8. What negative thought patterns do I have consistently?
9. Are my beliefs about life, religion, my kids, my family, my spouse, other people, or politics the absolute truth?
10. What do I feel passionate about, and how can I spend more time on my passion?
11. How does my work reflect my passions, skills, and interests?
12. How does my living space reflect my inner world?
13. How am I mistreating my body or compromising my health?
14. How do I feel I’m not deserving or worthy?
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15. How am I living a life someone else has defined for me?
16. What makes me consistently happy?
17. What is my vision for the next five years?
18. How am I living outside of my integrity and out-of-alignment with my values?
19. What am I leaving unresolved or unfinished that needs my attention?
20. What am I struggling against that I can simply release?
21. What deep needs do I have that aren’t getting met?
22. Where am I making my life more complicated or difficult than it has to be?
23. How could I be more engaged in life?
24. If I died tomorrow, what would I regret not doing?
25. How am I using tasks, television, work, or the computer to avoid facing something?
26. How much time do I spend dwelling on the past or worrying about the future?
27. What events from my past are hindering my ability to live in the present?
28. In what parts of my life do I need to create actionable goals?
29. In what ways am I allowing fear of change to hold me back from growth?
30. How am I spending too much time on things that aren’t my priorities?
31. Where do I need more learning or skills in order to make the next leap?
32. What do I allow to distract me from really living?
33. What has my intuition been telling me that I might be ignoring?
34. What really pushes my buttons that doesn’t need to?
35. What drains my energy (people or situations) and how can I change it?
36. How am I being irresponsible or unwise financially?
37. What parts of my home don’t reflect who I am?
38. What do I need to do to take the next big leap in my personal growth?
39. In what ways is longing for an outcome preventing me from enjoying the journey?
40. How am I holding back love for myself?
Questions to Ask Yourself in A Relationship
41. How am I not accepting someone I love for who they really are?
42. In what ways do I diminish other people to make myself feel better?
43. Where am I holding back forgiveness?
44. How do the people who surround me reflect who I am?
45. How do I allow other people to cross my boundaries?
46 .What vulnerabilities am I afraid to share with the people who love me?
47 .How am I getting too caught up in other people’s problems?
48. How am I fully present with the people I love when I’m with them?
49. How am I manipulating someone in order to get my needs met?
50. What relationships require more of my time and nurturing?
51. How have I created a miscommunication or misunderstanding?
52. How am I waiting for someone else to solve my problems?
53. What would my friends and family say are my strengths?
54. What would my friends and family say are my weaknesses?
55. How am I violating someone else’s boundaries when I know I shouldn’t?
56. How am I denying my own role in a relationship problem?
57. Where am I prioritizing money and material things over relationships and my values?
58. How am I helping others become their best selves?
59. How am I afraid to show or express love?
60. What expectations do I have for my kids that are more for me than them?
Now that you have 175 questions handy, which ones stick in your head the most, and how soon will you ask them of someone?
Or are you busy answering those questions for yourself? After all, if you want to be prepared for someone else’s answers to these questions, you should know your own.
So, spend some time using these questions to get to know yourself better than ever. Then practice working some of them into your next conversation — with your partner, with a friend, or with someone else you’d like to know better.
Here’s to deeper and more meaningful conversations. And may you and your relationships grow stronger than ever.