115 Deep Questions To Ask Your Friends

Updated April 6, 2024by Regain Editorial Team

There are some friends you have known for a lifetime and others you have just met. Some may be considered as close to you as a family; they feel like your brother, sister, or cousin. Others you see potential in – maybe with these friendships, you need time to nurture and grow.

In life, friendships are important. They are the people with whom you choose to surround yourself. When it comes to family, you get what you are born into. You may or may not get along with your family, and for many people, being with family can be more a source of stress than an exciting thing. 

Friends are people who have similar interests as you; you could have met them through school, work, or doing your favorite hobby. Some friends you meet when you are young, and then you grow into different people and lose touch, which is a normal part of life. As the popular saying goes, people come into our lives for “a reason, a season, or a lifetime.” 

The friendships that you keep can help ease the stress of other aspects of life. Friends can get you through a day of work and a lot of other stressful periods in life. They can help you navigate and process a future and previous relationship. And while friends are great to backboard against for ideas and life advice, if you need someone to talk to about your relationships, you can also seek professional help.

Being vulnerable with one another can strengthen friendships

When it comes to any relationship, the connection and bond grow with time. There may always be that desire to get to know each other better or look for ways to bond more. Relationships of any kind go through different growth phases, whether it’s with a friend or people you consider to be more than friends. The people involved will not get to know everything about one another in one day.

How to get to know someone

Often, you meet strangers and want to get to know them. For this reason, it may help to read tips to help you talk to strangers. Also, one of the most powerful and surest ways to get to know someone is by asking intentional questions, such as getting to know you questions. One way to help yourself connect easily and effectively with other people is by asking the right questions. This can change your life and help you to know how to harness each relationship. 

Asking deep questions can be very instrumental in enhancing your existing relationships or growing and building new ones. Also, knowing which deep questions to ask is a lot like a secret weapon, especially in social situations. You can choose to memorize some of your favorites or have a list of deep questions to ask on your phone, and you pull them out whenever the need arises. That way, you may rarely be at a loss for words in your relationships or any gathering where you find yourself.

However, it is important to consider the person(s) you are having the conversation with, your gut feeling, the mood or tone of the conversation, and the goal. This way, you will know which questions to use in each scenario and not ask the wrong questions to throw people off-guard or turn them off. 

Close friendships: Is there anything left to ask?

When you consider someone to be your "close friend" it likely does not take any effort to casually invite them for a coffee, dinner, or movie. How to ask a friend out usually depends on the person you are asking; you may need to know a little more about them, their interests, and what they enjoy doing before getting them to agree on going out with you.

Even in the closest of friendships, there are always new things to discover about one another, which can strengthen your friendship. Whether you feel as if you know your friends as well as you know yourself, or you are exploring a fresher friendship, there are likely still many deep personal questions to ask each other. Read ahead to discover a helpful list of 117 deep questions to ask your friends.


115 deep questions to ask your friends

  1. What makes you feel unstoppable?

  2. How do you see me?

  3. What emotion do you experience most frequently?

  4. If you could do anything for the rest of your life in the entire world today, what would that be?

  5. Do you think you are brave?

  6. What makes you feel super loved?

  7. Do you think people fall in love because the right person has arrived, or because the timing is right (regardless of whom the person is that they fall in love with)?

  8. What do you want people to feel when they’re around you?

  9. What is one dream you’ve never said out loud?

  10. What bad habits do you lie about or omit most often?

  11. If you had to change your name, what would you change it to and why?

  12. What makes you feel most alive?

  13. When do you feel the most vulnerable?

  14. What do you think makes me smile?

  15. How easy or difficult is it for you to show yourself love or speak kindly to yourself?

  16. What annoys you the most about people in three words?

  17. What scares you the most?

  18. What is more important to you in a dream job – status, power, or money – and why?

  19. Is there anything you see inside of yourself that makes you curious?

  20. What is that one embarrassing moment you have not told anyone about yet?

  21. What is the nickname that your friends have given you? What does it mean?

  22. Are you more afraid of death or not living?

  23. Where would you like to be in five years?

  24. Do you want kids? If so, would you prefer having a baby without a partner or a partner without a baby?

  25. What was the biggest mistake that impacted you the most in your life?

  26. What type of relationship did/do you have with your parents?

  27. Would you be with someone who doesn’t have the same personal beliefs as you?

  28. How would your best friends describe you?

  29. Do you usually follow your head or your heart?

  30. Do you prefer dating just one person and seeing where it goes or dating multiple people until you decide with whom you’re most compatible?

  31. How would you rank the following in importance: family, career, love life?

  32. What are the qualities you are looking for in someone you want to grow old with?

  33. What are you most grateful for in your life?

  34. If you could change anything about your past, what would it be?

  35. Where do you think you will be ten years from now?

  36. What is one thing you would like to change about yourself today, and why?

  37. Where do you go when you need some inspiration?

  38. Who is the first person you call when you are in trouble?

  39. What is the most memorable experience that you’ve gone through with someone?

  40. Would you put your family or your friends first if you had to choose one, and why?

  41. Why did your last romantic relationship end and what did this relationship teach you?

  42. Who was your favorite cartoon character when you were a kid?

  43. What is the best advice you’ve ever been given?

  44. If you could marry anyone in the world, who would it be and why?

  45. If a psychic with a crystal ball told you that you only had one year to live, what would you change in your life?

  46. What is your greatest fear?

  47. Do you think confessions make a relationship stronger?

  48. Have you ever judged someone for the dark secrets they told you?

  49. What has been the best phase in your life thus far?

  50. If you could choose one superpower, what would it be and why?

  51. What is your favorite childhood memory about a favorite teacher?

  52. What would you do if your parents raised concerns about your partner?

  53. Are you still in touch with your childhood friends?

  54. What do you do when you are angry?

  55. What is your biggest regret in life so far?

  56. What was your favorite romantic moment, and why?

  57. What are your beliefs about God or a higher power?

  58. Do you believe in soul mates from a past life?

  59. How long does it take you to trust someone?

  60. If you could move to a deserted island without your friends and family, would you do it?

  61. What are some things that you wished people knew about you?

  62. Do you believe that life after death is possible?

  63. If you got into an argument with your best friend over your lover when they aren’t around, would you stand up for your lover?

  64. What is your philosophy in life?

  65. Are you religious or spiritual?

  66. If you were given three things to make you happy, what would these be?

  67. Would you ever take back someone who cheated?

  68. What was the most important lesson of your life?

  69. What was the greatest struggle of your life?

  70. Is what you’re doing now what you always wanted to do growing up?

  71. What are your favorite songs, books, or movies of all time, and why did they speak to you so much?

  72. What makes you feel accomplished?

  73. What is a relationship deal-breaker for you?

  74. Are you more into looks or brains?

  75. Do you consider yourself an introvert or an extrovert?

  76. Which parent are you closer to, and why?

  77. What lies do you most often tell yourself?

  78. Would you relocate for love?

  79. Have you ever written in a journal?

  80. What legacy do you want people to remember about you after you’re gone?

  81. Do you think the present is better than 50 years ago? Why?

  82. What advice would you give to the current younger generation?

  83. What’s the most extreme example of poverty you have ever seen?

  84. What do a lot of parents do that screws up their kids’ development?

  85. What kind of parent do you think you will be?

  86. What life-changing event have you experienced?

  87. Who is that one person you can talk to about just anything?

  88. What is the weirdest thing you have ever eaten?

  89. Do you usually stay friends with your exes?

  90. How do you feel about giving your passwords to your partner?

  91. Is there such a thing as being ready for marriage?

  92. Have you ever lost someone close to you?

  93. What is your idea of a perfect date?

  94. If you are in a bad mood, do you prefer to be left alone or have someone to cheer you up?

  95. Which fictional character do you most relate to and why?

  96. Describe your ideal weekend.

  97. What do you think of having good friends of the opposite sex?

  98. When was the last time you broke someone’s heart?

  99. What are you most thankful for?

  100. Do you believe in second chances, and if so, why?

  101. How would you describe your first crush?

  102. What’s a guilty pleasure that people always misunderstand about you?

  103. Would you rather take a trip to the beach, the mountains, or an amusement park?

  104. What is something you have learned from your previous relationships?

  105. Do you judge a book by its cover?

  106. Are you more of a morning or night person?

  107. What is the craziest thing you've ever done?

  108. Are you confrontational?

  109. What are your thoughts on online dating apps?

  110. What is on your bucket list this year?

  111. When have you felt your biggest adrenaline rush?

  112. What is the craziest thing you’ve ever done, and would you do it again?

  113. If you could do anything knowing you would not fail, what would you do?

  114. If a genie granted you three wishes right now, what would you wish for?

  115. What do you think about when you’re by yourself?

For additional ideas, try searching online for “deep questions to ask your friends.” There are various websites that offer examples of conversation starters with your girlfriend or boyfriend.

Ilona Titova/EyeEm
Being vulnerable with one another can strengthen friendships

Whether you’re having drinks with the guys or a dinner date with your girls, these questions are sure to make any friend hang out interesting. Deep conversations can be intense, but the good thing about them is that they can be incredibly rewarding. While you are discovering quite a lot of new things about the other person, you can simultaneously realize many new things about yourself. This is because diving into deep questions can give us a better perspective. They help us to understand people and why they act the way they do.

Through the course of these discussions, you can form deep connections that you would not get from light-hearted chats. This doesn’t mean the small talks are not useful, either; it means that there is a time and place for different intensities of conversations. Deep questions can help you genuinely understand one another deeply and reflectively; you may each discover or better understand one other’s personal interests, thought patterns, drives, and other fun facts that were previously unknown or unclear. This way, you can move your friendship beyond a shallow level. Your knowledge of one another may broaden.

Seeking support for building friendships

There are many factors that can make it difficult to initiate or grow friendships with people. For instance, some people live with social anxiety or generalized anxiety disorder, which can cause the act of approaching someone, introducing yourself, and being vulnerable to feel like a heavy task. In other situations, maybe you have felt betrayed by a former best friend, or even lost a good friend, and you are experiencing symptoms of depression that cause you to withdraw or isolate yourself from others who could be great additions to your support system.

It may be worthwhile to consider online therapy as a way to form friendships aligned with your values and needs. On the one hand, an online therapist can help you uncover the reasons why you feel apprehensive or afraid about forming new bonds. Additionally, they can role play strategies that mimic social situations with you so that you can act confidently in the actual moment when an opportunity to strike up a conversation manifests.

Online therapy platforms like Regain enable participants to schedule sessions at convenient times – there is no need to sit on a waitlist while you hope to be connected with a caring, qualified counselor. You can even text your therapist directly, should you find yourself in a situation when you want to reach out to a new person. When you schedule appointments online with your therapist, you can meet with them from any preferred location with a reliable internet connection, as well.

You may be curious if online therapy is as effective as traditional in-person counseling; in so many scenarios, this is true! Online counselors can and do utilize many approaches that in-person counselors employ, like cognitive behavioral therapy (CBT), a form of talk therapy that helps people reframe negative thought patterns into more empowering ones. In one recent study, researchers assigned 44 people with social anxiety disorder to two treatment groups: a waitlist control group and a cohort that would receive internet-based CBT. After a pre-assessment, eight-week post-assessment, 15-week post-assessment, and three-month post-assessment, practitioners uncovered that those in the internet-based CBT group experienced significantly reduced social anxiety symptoms compared to the waitlist control group participants. 


While it can feel nerve-racking to strike up a conversation new or take your existing friendship to a deeper level, you may often find that making the effort is highly worthwhile. Having someone you can be vulnerable and open with – without fear of judgment – can have a tremendous impact on your confidence and overall wellbeing. If you feel emboldened to use some of these questions to strengthen existing friendships or build new ones, that’s excellent! If you could use some extra support, know that the compassionate licensed therapists at Regain are available to help you achieve your goals. Take the first step today in reaching out.

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