There will come a time in your friendship that you’ll feel the need to learn more about the person you’ve come to know. So soon, those shallow conversations will become deeper, and you’ll find yourself in the position to ask your friend more personal questions to tap into their personality, their history, and their inner most thoughts.

While a lot of people might feel vulnerable when being asked intimate, personal questions, there are certain questions that can provoke deep answers without having to put that person on the spot. If you’re wondering how you can get to know your friends better and you want to come prepared with the right through provoking questions, then read through this ultimate list of personal questions you can ask your friends or your love interest.

Personal Questions for Friends

Personal Questions for Friends

A deep, sturdy friendship is founded on mutual love and respect. And we all know that the more you get to know someone, the easier it becomes to love them and treat them with high regard. If you want to deepen your friendships, then these personal questions to ask your friends can be perfect to help you feel closer and more endeared to the friends you have.

  1. What’s one secret that you can share with me?
  2. What’s the biggest lesson you’ve ever learned in life?
  3. If you could change anything about your childhood, what would it be and why?
  4. What’s something that you feel very passionately about?
  5. How can our government improve the quality of life for people in the lowest socioeconomic classes?
  6. If you found out that you’re dying in a month’s time, what would you do with the time you had left?
  7. What do you consider your biggest accomplishment and why?
  8. If you could be famous for a day, what would you do?
  9. If you could have a million dollars fall into your lap right now, but you can’t spend any of it on yourself, how would you spend the money?
  10. What’s one thing that you think you’re really good at that other people might typically have trouble with?
  11. If you would become a parent, what’s something that your parents used to do to you that you would never do to your own child?
  12. What’s your biggest insecurity?
  13. If you could go back in time and change one thing, what would it be and why?
  14. If you could sit down and have a meal with someone – anyone whether dead or alive – who would it be and why?
  15. What’s a life lesson that you think would make the world a better place if everyone learned it?
  16. If someone told you that you would lose all of your earthly possessions tomorrow and you wouldn’t have anywhere to live, what would you do?
  17. What’s something that someone might do to you that you could never forgive?
  18. What’s your biggest character flaw?
  19. If there’s one thing you could change about your personality, what would it be and why?
  20. What is a bad habit you have that you struggle to eliminate from your life?
  21. If you could take a single photograph to represent your whole life, what would it be a picture of and why?
  22. What’s something that most people have but rarely appreciate?
  23. What’s something that you love but feel embarrassed about?
  24. What do you think is the secret to happiness?
  25. How can a person become truly successful?
  26. What is the measurement of a person’s success?
  27. What’s your biggest fear and why?
  28. Do you believe in the saying “forgive and forget?”
  29. Do you think that time does heal all wounds?
  30. Do you think that youth is an advantage, or are people of all ages capable of doing the same things?
  31. If you could dive into a pool of anything right now, what would it be a pool of?
  32. What would you want to be written on your tombstone?
  33. What was the best gift that you ever gave someone?
  34. Was there ever a time when you felt excited to go somewhere, only to have the plans canceled?
  35. What was the most hurtful thing that anyone has ever told you?
  36. If you would come face to face with someone who hurt you in the past, what would you tell them?
  37. What do you think is the worst feeling that anyone could possibly feel?
  38. What have you learned from previous encounters with toxic people?
  39. How would you describe a toxic person?
  40. If someone significant to you – like a parent or sibling – were too toxic to be around, what would you do and how would you deal with it?
  41. What’s the worst thing a person can be?
  42. Do you think that a person’s past defines their future?
  43. When would you consider yourself to be truly successful or accomplished?
  44. What’s more important – stability or excitement?
  45. Is there a memory you have that you hope you’ll never forget?
  46. Do you think that people can get along even when they have absolutely nothing in common?
  47. If you had to live in a remote location for 5 months and you’re only allowed to bring three things from your bedroom, what would they be and why?
  48. If you discovered today that you were adopted, what would your reaction be?
  49. Is it always important to be honest? Or are there some instances when honesty is only a second priority?
  50. Is there any part of your life that you feel needs improvement? What is it and how do you think you can work to achieve that improvement?

Personal Questions to Ask a Love Interest

Personal Questions to Ask a Love Interest

Maybe you’ve made a new love connection, or perhaps you’ve been dating for a while. Whatever the case, there’s always a benefit to learning more about your special someone. If you want to enrich the bond between you and your love interest, then it pays to ask the right personal questions. Try to roll out these intimate questions and provoke deep, meaningful answers from your love to help strengthen your relationship and learn more about the person you’re on this journey with.

  1. In a relationship, does a person’s past matter?
  2. What is your favorite non-physical quality that you look for in another person?
  3. Was there ever a time when you felt you were giving as much love as you could muster, but it was unappreciated or it went unnoticed?
  4. How do you think you best express your love to other people?
  5. How do you like to receive love from others?
  6. What’s something that when done to you, makes you feel unloved or unappreciated?
  7. Are lasting relationships the result of a good match, or the result of hard work?
  8. What’s more important in a relationship – honesty or respect?
  9. What’s the worst thing about being in a committed relationship?
  10. Do you think that two people should start living together before marriage?
  11. How do you define the ideal relationship?
  12. What are your three ingredients to a happy lasting relationship?
  13. How do you know if you should keep holding on or if you should let go?
  14. What’s the most common way that past lovers have typically misunderstood you?
  15. When you’re in an argument with your significant other, do you like to talk it out or do you prefer giving the cold shoulder?
  16. Do you think it’s reasonable for a couple to go on a break if they’re not seeing eye to eye?
  17. What’s one surefire way to resolve any conflict within an intimate relationship?
  18. What is a toxic relationship, how would you define it, and how would you deal with it?
  19. What are your personal flaws that you think get in the way of your relationships?
  20. What’s your biggest fear when it comes to love and relationships?
  21. What was the biggest lesson you’ve learned from past relationships?
  22. Do you believe that we ever truly stop loving people once they leave our lives, or do we continue to love them in more subtle ways?
  23. What’s your surefire method for getting over a past lover?
  24. Is there anything that changes about your mood, disposition, or personality when you’re in a healthy, stable relationship?
  25. How would you define a successful relationship?
  26. What’s a simple, harmless kink that a person might have that’s a major turn off for you?
  27. What are your three ingredients for the perfect mate?
  28. Do you think that people should have a lot in common with one another for their relationship to work out?
  29. Do you think that two people who have absolutely nothing in common could still successfully establish a romantic relationship?
  30. If your partner ended up telling you something that really hurt your feelings, would you tell them that you were hurt or would you clam up and wait for them to figure it out?
  31. Do you consider yourself a high-maintenance partner?
  32. What’s something that you could never give your partner even if they begged you for it?
  33. When you’re in a relationship, do you feel more distracted or inspired?
  34. What do you think people get into relationships for?
  35. What’s the best way you can spend your time with your partner?
  36. Do you think that couples should pool their money and manage it together, or do you think it’s more important for each of them to have their own funds?
  37. What’s a mistake that your partner might make that you could never be able to forgive?
  38. When do you know when you’re in love with someone?
  39. If you could make the perfect partner, what qualities would he or she have?
  40. Do looks matter in a relationship, or is it all a part of the courtship phase?
  41. Do you have a hard time letting go of past relationships or do you move on quickly?
  42. Why do you think most relationships these days don’t last very long?
  43. Would you let your partner help you through a challenge at work, or do you prefer working through similar problems alone?
  44. If your partner apologizes for a mistake once, but ends up doing it again, are those grounds for a break up?
  45. Do you consider flirting to be cheating?
  46. What’s the first thing that attracts you to a person?
  47. Do you think that differing spiritual or religious beliefs and practices can get in the way of a healthy relationship?
  48. What do you think stops people from having healthy, functional relationships?
  49. Do you see yourself as someone who could possibly be in a relationship with the same person for the rest of your life?
  50. Do you think it’s easier to give love or to receive love?
  51. What are the essential aspects of a relationship that every couple needs in order to claim a successful partnership?
  52. What does it mean to be a good partner to your significant other?
  53. What do you think it means for partners to be ‘intimate’ with one another? Does it always mean sex? Or are there other ways that couples can achieve and enjoy intimacy?
  54. What’s one behavior that you can never tolerate in a relationship?
  55. Is a long-distance relationship something you think you could deal with, or do you feel most at ease when you and your partner can get together and spend time with one another physically?
  56. If your partner ends up doing something that upsets you, what’s one thing they can do to apologize that will always work on?
  57. In a relationship, are you the first one to apologize, or do you wait for your partner to come up to you first?
  58. What do you think is your ultimate couple goal?
  59. What are some things you like to do to encourage your partner to be the best version of themselves?
  60. Is there a past lover that you might have caused hurt or pain? What would you say to them now if you were face to face with them?