130+ Deep Questions to Get To Know Friends Better

Are you tired of the same old small talk with your friends? Has “How’s the weather?” become just another cliché? Well, it’s time to ditch the shallow chit-chat and dive into the deep end of the conversation with this list of deep questions for your friends!

These carefully crafted questions will spark meaningful discussions, unveil hidden layers, and unlock the secret chambers of your friends’ minds. We’re talking about questions that will make you ponder the mysteries of life, re-evaluate your priorities, and maybe even shed a tear or two (in a good way, of course).

Whether it’s a casual hangout, a weekend getaway, or a cozy night in, our thought-provoking inquiries are perfect for bonding sessions with your besties. Say goodbye to awkward silences and hello to soul-stirring conversations that’ll leave you feeling like you’ve just had a group therapy session.

So, grab your favorite beverage, gather your closest pals, and get ready to embark on a journey of self-discovery and personal growth.

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Deep Questions for Friends

The below questions are designed to open up conversations and stimulate meaningful dialogue. They are perfect for inviting people to think more deeply about themselves and their relationships with others, as well as the world around them.

Questions for personal growth and self-reflection.

This first section of questions focuses on personal growth and self-reflection. Throwing these topics out to your bestie will help them to reflect on areas of improvement, strengths and weaknesses, and developmental goals, and consider what lies ahead. Additionally, it will allow you two to connect over some meaningful introspection.

1. What is your biggest fear?
2. What is your greatest accomplishment? Why are you proud of it?
3. If you could change one thing about your past, what would it be?
4. What do you consider your greatest strength and weakness?
5. How do you handle stress or difficult situations?
6. What are some habits you’re trying to break?
7. Are there any skills you’re currently working to develop?
8. How have you evolved as a person since the Covid-19 pandemic?
9. Do you think the Covid-19 pandemic affected you? Why or why not?
10. What is the defining moment in your life that shaped who you are today?
11. If you could have any superpower, what power would best help you achieve your dreams?
12. How do you define success, and do you feel you’re on your way to achieving it?
13. In what ways do you practice self-care and maintain mental well-being?
14. What motivates you to keep going during tough times?
15. Which of your school teachers had the biggest effect on who you are today? Were they your favorite teacher?
16. What does personal growth mean to you, and how do you actively pursue it?
17. How do you approach setting and working toward personal goals?
18. When faced with criticism, how do you react and learn from it?
19. Are you an introvert or an extrovert? Do you like what you are?
20. What have you always wanted to learn or try but haven’t yet?
21. How do you maintain a healthy work/life balance?
22. Who is someone you’d like to be more like?
23. Are there any bad habits that you’re trying to kick?
24. When was the last time you really unplugged from it all?
25. What is your favorite childhood memory?
26. How do you stay true to yourself when faced with external pressures or expectations?
27. In what ways do you step out of your comfort zone to grow as a person?
28. What was a major change for you, how did you cope, and how did it affect the rest of your life?
29. How is your mental health these days? What are you doing to improve or maintain it?
30. If you could only bring three items with you on a deserted island, what would they be and why?
31. What role does self-reflection play in your everyday life, and how do you practice it?
32. How do you feel like you maintain a sense of purpose and direction in your life?

Not-so-random questions about dreams, goals, and aspirations.

There is nothing quite like daydreaming with deep yet fun questions and your BFF. This section of questions focuses on your dreams, goals, and aspirations.

These deep questions for friends will help to uncover each other’s ambitions and visions for the future. It can also bring to light any underlying doubts or anxieties about pursuing them. Ask away and open up conversations about where you both want to be in life!

1. How would you define the perfect life?
2. If you could achieve anything within the next five years, what would it be?
3. What steps are you actively taking to reach your goals?
4. What long-term goal have you set for yourself, and how do you plan to make it happen?
5. If you could have your dream job and money wasn’t an issue, what would it be and why?
6. What are some short-term goals you’re currently working towards?
7. How do you stay motivated and focused on your aspirations?
8. Did a specific person or event inspire your goals?
9. Have your goals and aspirations changed over time? If so, how and why?
10. What motivates you to get out of bed every day?
11. What resources or support do you feel you need to achieve your dreams?
12. How do you measure your progress toward your goals, and how do you celebrate your achievements?
13. Are there any fears or challenges holding you back from pursuing your dreams? How do you plan to overcome them?
14. How do you balance pursuing your dreams with other aspects of your life, such as relationships, work, and personal well-being?
15. How do you prioritize your goals when faced with competing interests or limited time?
16. What is the biggest thing holding you back right now?
17. What is a dream or goal that you’ve had since childhood? Are you still working towards it?
18. If you had unlimited resources, what would you do? Work? Travel? Etc.
19. How do you handle setbacks or obstacles while working toward your goals?
20. What has been your most significant achievement in pursuing your dreams so far?
21. Do you need a plan or roadmap for achieving your aspirations? Or do you go with the flow?
22. Do you have any mentors? If so, how do you seek guidance or mentorship to help you reach your goals?
23. How do you stay adaptable and open to change as you work towards your aspirations?
24. Have you ever had to let go of a dream or goal? If so, why and how did you cope with that decision?
25. How do you ensure your goals align with your values and contribute to your happiness and well-being?
26. If a genie gave you three wishes, what would they be?

Bucket list questions about values and beliefs.

Use these questions to better understand each other’s core principles and ideals. Asking your best friend these thought-provoking questions can give you an insight into the things that truly matter to them. They can also help both of you appreciate your unique perspectives while still finding common ground.

1. What are the core values you believe in and try to follow?
2. How do your beliefs or religion shape your actions and decisions?
3. Are you religious? Why or why not?
4. Have you ever questioned or changed your beliefs? Why?
5. How has your upbringing shaped what you believe in today?
6. Can you share an experience that significantly impacted your beliefs?
7. How do you handle situations where your values conflict with those of others?
8. In what ways do your values influence your personal and professional relationships?
9. What role do your beliefs play in your overall sense of identity?
10. Did your favorite book or movie influence your worldview?
11. What effect did family members have on your current beliefs?
12. How important is it for you to surround yourself with people who share similar values and beliefs?
13. Have your values or beliefs ever been challenged? How did you respond to that challenge?
14. How do you strive to live in alignment with your values daily?
15. Are there any values you’ve adopted from other cultures or traditions that resonate with you?
16. Do you have any beliefs that directly contradict social norms?
17. Is it important for you to engage in self-reflection and introspection to examine your values and beliefs?
18. In what ways do you actively work to broaden your understanding of different belief systems or perspectives?
19. What role do your values and beliefs play in your decision-making process?
20. Can you think of a time when your values or beliefs positively impacted someone else’s life?
21. How do you navigate situations where your values may be at odds with your professional obligations?
22. How have your values and beliefs evolved, and what factors have contributed to those changes?

Personal questions about relationships and connections.

Questions about relationships and connections can help two friends gain a deeper understanding of each other’s interpersonal dynamics. Asking your best friend these questions will not only reveal more details about their current relationships but also allow you to explore the importance of connection in their life.

These questions can help uncover the multitude of ways they bond with family, partners, and friends and how they feel about the relationships in their lives.

1. What qualities do you value most in a friend or significant other?
2. How do you handle conflict in relationships?
3. What has been your most challenging experience in a relationship, and what did you learn from it?
4. How do you balance time between your friends and your relationship?
5. What is your love language? Do you understand your partner’s love language?
6. Can you share an experience that strengthened a bond with someone in your life?
7. What role does trust play in your relationships, and how do you build and maintain it?
8. How important is open and honest communication in your connections with others?
9. What’s your biggest regret in a past romantic relationship?
10. How do you balance your personal needs and boundaries with the needs of your relationships?
11. What are some strategies you use to resolve misunderstandings or disagreements with loved ones?
12. How do you handle and cope with a breakup?
13. Who is your best friend, and why?
14. How do you approach finding a partner?
15. Do you enjoy small talk, or do you prefer to get to the deep stuff quickly?
16. What do you do to connect on a deeper level with people?
17. How have your past relationships influenced your approach to current and future partners?
18. What are your favorite things to do on a first date?
19. How do you handle relationship stress or external pressures that may impact your connections with others?
20. What role does empathy play in your relationships, and how do you practice it?
21. Do you believe in soulmates?
22. What is your biggest pet peeve that you can’t get over in a potential friend?
23. How important is it for you to maintain a diverse group of friends or connections with different perspectives?
24. In what ways do you support and encourage the personal growth of those close to you?
25. What does being a good friend look like to you?
26. How do you recognize when a relationship is no longer serving you or the other person positively?
27. What is a deal breaker for you when looking for a partner?
28. Have you ever had a long-distance relationship? If so, how did it go?
29. In what ways do you seek to improve your relationship skills and understanding of others’ needs?
30. What defines close friends to you?
31. How has your approach to relationships and connections evolved, and what factors contributed to these changes?
32. What role does social media play in your relationships?
33. If you had to ask your best friend to describe you in three words, what would they say?

Deep conversation starters to ask about life experiences and lessons.

Life experiences, both positive and negative, shape us into who we are today. Asking your friend questions about these types of experiences can help deepen your understanding of their life journey thus far.

You may learn lessons that have shaped their current outlook on life, as well as how they handle different situations or problems. These questions will give you insight into how they view the world and what matters most to them.

1. What has been the most transformative experience in your life?
2. Do you believe in second chances? Is it different for you vs. other people?
3. What was your biggest failure, and how did you grow from it?
4. If you could share one piece of advice with your younger self, what would it be?
5. What coping mechanisms do you rely on during a challenging time?
6. In what ways has your most significant failure shaped your perspective on success and personal growth?
7. Who are the people you lean on during big life changes?
8. How have your relationships been affected by these pivotal moments in your life? Either romantic or not.
9. If you could go back in time, would you change anything about a difficult experience? Why or why not?
10. How do you plan to use the advice you would give your younger self to guide your future actions and decisions?
11. Can you share an experience that taught you an important lesson about life?
12. How do you apply the wisdom gained from your life experiences to your personal and professional endeavors?
13. What is the most valuable piece of advice someone has ever given you, and how has it impacted your life?
14. How do you approach new challenges or opportunities with the lessons you’ve learned from past experiences?
15. Can you recall when you had to step out of your comfort zone? What did you learn from that experience?
16. What TV show character do you feel most similar to, and why?
17. In what ways do you share the lessons you’ve learned with others, such as friends, family, or colleagues?
18. What’s the weirdest thing or unexplainable experience that has happened to you?
19. How do you maintain a growth mindset and continue to learn from your positive and negative experiences?
20. What is your favorite place to visit, and what meaning does it hold for you?

Learn about hopes, fears, and the future.

Asking your friends these good questions about their hopes, fears, and future can open up an honest conversation about what matters to them. It will help you gain insight into their values and dreams for the future. These questions can also be useful for learning how they deal with fear or uncertainty in life.

1. Do you have a legacy in mind that you want to leave?
2. What is something you want to achieve before you die?
3. What about the future excites you? What scares you the most?
4. What steps are you currently taking to achieve the goals or milestones you wish to reach before you die?
5. How do you manage your fears and uncertainties about the future while staying focused on your aspirations?
6. In what ways do you stay informed about trends, advancements, or changes that may impact your future?
7. How do you balance long-term planning with embracing spontaneity and living in the present moment?
8. What role do your relationships and connections play in shaping your hopes and fears for the future?
9. In what ways do you seek support or guidance from others when navigating your aspirations and concerns about the future?
10. How do you prioritize your goals and aspirations amidst competing interests and responsibilities?
11. Can you recall a time when you overcame a fear or achieved a significant milestone? What was the experience like?
12. How do you ensure that your hopes and dreams remain realistic and attainable while still challenging yourself?

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Closing Thoughts

Ultimately, these deep questions for friends can help us better understand each other’s life experiences and gain insight into our shared hopes, fears, and plans. In addition, by exploring personal stories and reflections on meaningful moments in life, we can foster deeper connections with those who matter most to us.

Whether it be sharing advice for our younger selves or talking about how best to manage our fears and uncertainties, conversations based on thoughtful questions can help us feel more connected to the people we care about. These topics may lead you to find out that your friend is going through something difficult. Be prepared with what to say by reviewing these “Comforting Words for Friends Going Through Tough Times.”

By reflecting on these questions together, we can draw strength from one another’s life stories and gain insights into approaching new challenges with resilience. So, don’t hesitate to ask your friends meaningful questions—it’s how we tell the difference between acquaintances and real friends.

Want to lighten the mood with more chill conversation starters? Pick a prompt from our list of “200 Truth or Dare Questions for Adults.”

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Frequently Asked Questions