120+ Deep Questions to Ask Friends And Uncover Long-hidden Secrets

Bookmark these deep questions to ask friends and take your friendship to a whole new level. They are great conversation starters to get the cat out of the bag!

Anubhuti Mishra
Written by Anubhuti Mishra , Relationship Expert
Updated on Sep 30, 2024 | 12:29 PM IST | 3.3K
Deep Questions to Ask Friends
Deep Questions to Ask Friends

To initiate interesting conversations with your besties, you need a set of deep questions to ask friends prepared. You might know the smallest details of your BFFs but there’s always a scope to read their minds and understand them beyond the surface level. 

Your choice of questions about relationships, life, success, and failure will act as a two-way street. The flow of your deep conversations will determine your rapport, strengthen your connection, and deepen your bond, taking your friendship to a whole new level. 

Asking deep questions to one another is not just a way to know them better but a two-way street that fosters a sense of belonging and promotes emotional well-being. With a willingness to share thoughts and experiences, you and your friends can discover different and more serious versions of yourselves. 

Whether he or she is your best friend, boyfriend, or girlfriend, show your desire to solidify your companionship with our list of questions given below.

 

Deep Questions to Ask Your Friends And Soldify Your Connection

Deep Questions to Ask Your Friends

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

2. What makes you feel super loved?

3. How would your best friends describe you?

4. What makes you feel unstoppable?

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

6. What is your favorite hobby?

7. What’s your guilty pleasure?

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

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9. Do you think you are brave?

10. What do you feel the most guilty about?

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

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

13.  What emotion do you experience most frequently?

14.  What's the biggest lesson your last relationship taught you?

 

Deep Questions to Ask a Boyfriend And Know Him Better

Deep Questions to Ask a Boyfriend

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

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

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

18.  What are you most proud of about yourself?

19.  What is your idea of a dream proposal?

20.  What’s been on your heart and mind recently?

21.  Who do you wish you could reconnect with?

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

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23.  What scares you the most?

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

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

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

Read More: 270+ Questions to Ask Your Boyfriend And Know Him Better

 

Deep Questions to Ask Your Girlfriend And Spill the Beans

Deep Questions to Ask Your Girlfriend

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

28.  What would you like to accomplish in life?

29.  Do you believe in love at first sight?

30.  Did you grow up in an emotionally supportive environment?

31.  What values are most important to you?

32.  Who are you most like in your family?

33.  What really frustrates you?

34.  What stresses you out the most?

35.  Who in your family do you struggle with?

Read More: 200+ Questions to Ask a Girl And Keep the Conversation Flowing

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Deep Questions to Ask Your Best Friend About Relationships

Deep Questions to Ask Your Best Friend

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

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

38.  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)?

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

40.  How do you cope when things get hard?

41. 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?

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

43. What brings you joy?

44. If your exes were all stuck in a room together, what would they say about you?

45.  What is the most important relationship in your life?

46. What does it mean to be a good friend to you? 

 

Deep Questions to Ask a Friend About the World

Deep Questions to Ask a Friend About the World

47.  If you had a whole day where you could do anything you wanted, what would you do?

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

49.  If you could erase one technological advancement from the world, what would it be?

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50.  If you could choose any decade to live in, which one would you choose?

51.  What's something about the modern-day world that bothers you, and what’s something about it that brings you joy?

52.  If you could live a different life, what would it look like?

53.  Who sticks out as being an early positive influence in your life?

54.  If you could leave a “mark on the world” that preceded you, what would it be?

55.  What is the most important lesson you've learned in the past year?

56.  Do you believe in fate, or do you think we have control over our own destinies?

57.  What makes your life feel purposeful? 

58.  What is one thing that society has lost that you wish we could get back?

59.  Do you regret the path your life has taken to this point?

60.  Do spirituality or religion play any role in your life? Why or why not?

61. Who is most important to you now?

62.  Do you have any secrets that would change your whole life if they became public knowledge?

63. What are your best and worst childhood memories?

64.  If you could erase the bad memories from your mind, would you?

65.  Would you trade a long life for a short life full of distinction and success?

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Read More: 50 Poems About Friendship That Talk About Pure Love And Gratitude

 

Deep Questions to Ask Friends When Bored

Deep Questions to Ask Friends

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

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

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

69.  What makes you feel most alive?

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

71.  When do you feel the most vulnerable?

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

73.  What do you want people to know about you?

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

75.  How do you like to receive care?

 

Deep Questions to Ask Your Friend About Life And Death

Deep Questions to Ask Friends

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

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

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

79.  What is your life’s biggest goal?

80.  What are your current priorities in this season of your life, and why?

81.  What is your greatest accomplishment?

82.  Would you rather people perceive you as being kind, smart or attractive?

83.  What do you need more of in your life?

84.  What are the core principles that guide your decision-making and actions in life?

85.  What keeps you up at night?

86.  How do you define happiness, and what do you do to cultivate it in your life?

87.  What are you still hoping to accomplish?

88.  What do you need less of in your life?

Read MoreHow to Make a Girl Like You over Text And Win Her Affection

 

Deep Questions to Ask a Best Friend About Success And Failure

Deep Questions to Ask Friends

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

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

91.  How would you like people to experience you? What kind of person do want to be in the world?

92.  What do you feel has been your greatest “win” so far in life?

93.  Looking back on your life, who or what makes you instantly light up?

94.  What are your biggest fears, and how do you cope with them?

95.  How did you feel about where you grew up?

96.  Is there a time when you did something that seemed so out of character that most people wouldn’t believe it?

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97.  Are you satisfied with your current career trajectory? 

98.  What's your definition of success, and how are you working to achieve it?

99.  What’s a challenge you’ve recently overcome or are currently facing?

100.  If one wish of yours could come true, what would it be?

101.  What is the most trouble you’ve ever been in?

102.  Do you ever feel like a failure?

Read More: 150 Engaging Questions to Ask a Friend for Great Conversations

 

Deep Questions to Ask a Friend Over Text And Get Philosophical

Deep Questions to Ask Friends

103.  What fictional world would you most want to live in?

104.  If your inner monologue was a book, what genre would it be?

105.  What's the most morally questionable thing you would do for a lot of money?

106.  What three words describe what you’re most grateful for?

107.  If aliens came to Earth and you were the first person they saw, what would you do to communicate to them that you were friendly?

108.  What would your role be in the zombie apocalypse?

109.  What skill is the closest thing you have to a superpower?

110.  If you could be famous, what would you most want to be famous for?

Read More: 100+ Great Questions to Ask to Get to Know Someone Better

 

Deep Questions to Ask a Group of Friends for Fun And Laughter

Deep Questions to Ask a Group of Friends

111. If you could relive one day of your life, which day would it be and why?

112. What advice would you give to your younger self?

113. If you could know the day of your passing, would you want to know?

114.  If you could travel anywhere, where would you go?

115.  If you could meet anyone in the world, alive or deceased, who would it be?

116. If you only had 24 hours left to live, how would you spend it?

Read More: 21 Questions Game: 101 Best Questions for an Exciting Game Night

 

Deep Question to Ask Your Best Friend About Yourself

Deep Question to Ask Your Best Friend

117. What do you think makes me smile?

118. How do you see me?

119. What do you like the most about me?

120. What is that one thing you wish to tell me without regretting?

121. How do you feel about me?

122. Have you ever thought about me in your hardest and happiest times?

123. How you do explain my current relationship with you?

 

What Is the Importance of Asking Deep Questions?

Importance of Asking Deep Questions

In order to explore an interesting topic and uncover the long-hidden secrets, you need a bank of thoughtful questions. They are not only conversational starters but topics that keep your discussion flowing.

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Asking deep and personal questions involves complex thought processes that are either emotional or philosophical. They require vulnerability to build bonds and strengthen connections. Plus, a thoughtful and mindfully crafted question bank revolving around personal values, interpersonal relationships, family dynamics, aspirations, fears, and challenges helps one understand the responder better. In fact, both parties can actively explore a genre together and discover new insights. 

Nonetheless, creating a set of deep questions to ask friends can strengthen your connection and develop empathy toward each other. Whether you are feeling bored or spending time at a fancy restaurant with your best friends, consider asking any of the above-mentioned questions. Doing so will not only elicit positive emotions but also initiate meaningful conversations that are thought-provoking. 

FAQ's

How can one know a friend better?
One can know a friend better by asking a few deep questions about themselves, career, relationships, success, and failure.

How do you show your female friend that you are interested in her?
You can ask your female friend deep questions about her family, relationship, and family plans.

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About The Author
Anubhuti Mishra
Anubhuti Mishra
Relationship Expert

A marked inclination toward understanding human emotions and relationships led Anubhuti to become a certified Relationship Expert. With dual

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