100+ Deep & Interesting Questions to Ask Your Friends

In the process of getting to know your friends, you’ve probably already covered basics like “What’s your favorite color?” and “Who’s your favorite musician?” But what if you want to ask deeper, more thought-provoking questions about how your friend sees the world and what they want out of life? You’ve come to the right place! We’ve compiled a list of deep questions to help you get a meaningful conversation going and grow even closer to your friends. Keep reading for everything you need to know about starting a deep convo with your pals!

Deep Questions for Friends

What is the best advice you’ve ever received?
Which of your qualities are you most proud of?
Where in the world do you feel the happiest?
Have you ever been in love?
Do you believe in soulmates?
What do you think it means to be a good friend?
What does success mean to you?

Section 1 of 8:

Deep Questions to Ask Friends about Themselves

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Ask these questions to learn about your friend’s deepest thoughts. These inquiries make excellent conversation starters and they’ll also encourage you to open up and be vulnerable with each other, which can bring you closer together. ^{[1]
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- Which of your personality traits are you most proud of?
- What’s one thing you would change about yourself if you could?
- What brings you the most happiness in life right now?
- Where in the world do you feel the most peaceful and safe?
- What’s the best gift you ever received?
- What’s the best advice you’ve ever been given?
- Is there anyone you’ve lost touch with whom you wish you could reconnect?
- How do you think your closest friends would describe you?
- Is there a specific event in your past that you think was a major turning point for you?
- If you could erase one memory from your mind, which would you pick?
- What keeps you up at night?
- If you had one day left to live, how would you spend it?
- What’s on your bucket list?
- What scares you the most?
- What gives you hope on hard days?
- When do you feel the most alive?
- When do you feel the most vulnerable?
- Do you think you’re kind enough to yourself, or do you think you’re too self-critical?
- What’s an embarrassing thing that’s happened to you that you’ve never told me about?
- Do you think your personality stays the same around different people, or does it change depending on the setting?
- Which of your physical traits makes you feel the most beautiful?
- How do you like to be comforted when you’re struggling?
- What is one surprising thing most people don’t know about you?
- What’s the last lie you told, and why did you tell it?

Section 2 of 8:

Deep Questions to Ask about Love

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Use these questions to reveal your friend’s views on romance. These questions can help you learn more about what your friend needs to feel emotionally supported in both romantic and platonic relationships, and you may also bond over similar experiences you’ve had in your dating lives.
- Have you ever been in love?
- Do you believe in love at first sight?
- Do you believe everyone has one true soulmate, or do you think people can have multiple soulmates?
- Do you think you’ve already met your soulmate?
- If your exes were asked to pick three words to describe you, what do you think each of them would say?
- What’s your love language?
- What are your relationship deal-breakers?
- What’s the biggest lesson you learned from your last relationship?
- What kind of person do you picture yourself ending up with?
- Do you have a specific type?
- What would your dream proposal look like?
- Do you believe in monogamy?
- Is getting married a goal you have in your life?
- Who was your first love?
- Do you fall in love quickly, or does it take a while for you to fall in love with someone?
- What is the most random, strange, or unconventional thing that you find attractive in another person?
- What conventionally attractive traits do you actually find unattractive?
- Which do you think is more important, physical compatibility or emotional compatibility?

Section 3 of 8:

Deep Questions to Ask about Friendship

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Ask questions about friendship to strengthen your bond. These types of inquiries will help you to learn more about how your friend views platonic relationships in general, as well as how they view their specific relationship with you.
- What do you think it means to be a good friend?
- Have you ever gone through a friendship breakup? What caused it?
- Do you tend to befriend people who are similar to you, or do you think opposites attract?
- When did you feel most betrayed by a friend? How did you deal with it?
- How do you deal with conflict in relationships?
- Who have you been friends with the longest? Why do you think that relationship is so strong?
- What’s your favorite thing about our friendship?
- Is there something I do that makes you feel especially loved or supported?
- Is there any part of our relationship you would change if you could?

Section 4 of 8:

Deep Questions to Ask about Family

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Discover how your friend’s family shaped who they are today. If you want to connect with your friend on a deeper level and get to know them even better, try asking these questions about their relationship with their family. You may even find that you shared some common experiences growing up!
- What is your favorite childhood memory?
- What is your favorite family tradition?
- Did you have a favorite holiday to celebrate with your family when you were little?
- What was the most memorable vacation you went on as a child?
- Did you have a pet when you were growing up?
- Did you enjoy growing up in your hometown?
- Who did you feel closest to in your family while you were growing up?
- Is there a story of how your parents chose your name?
- If you had to describe your family in one sentence, what would it be?
- Which family member are you currently closest to?
- Which family member do you look up to the most?
- Which family member are you the most similar to?
- Do you think it’s better to have siblings or be an only child?
- Were your parents strict, or were they more laid-back?
- How did your parents meet?
- Do you have a good relationship with your parents?
- Are you closer to one parent than the other?
- Which of your parents’ traits do you admire the most?
- What’s the biggest lesson your parents taught you?
- Are you happy with the way your parents raised you? What things would you do the same if you had your own children? What things would you do differently?
- How close are you to your family now? Do you wish you were closer, or do you wish you had a bit more space from them?

Section 5 of 8:

Deep Questions to Ask Friends about Success & Goals

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Ask these questions to uncover what your friend wants out of life. Life goals are a pretty important topic, and it can definitely start a deep and meaningful conversation between the two of you. Plus, once you know each other’s biggest goals, you’ll be better equipped to support each other and cheer each other on as you pursue them.
- Are you happy in your current career path?
- What would you do with your life if money was not a concern?
- What was your dream job when you were growing up?
- What career advice would you give your younger self if you could travel back in time?
- Which of your previous jobs was your favorite? And least favorite?
- Who is the best boss you ever had? What do you think made them such a good leader?
- What would you say you’re most passionate about at this moment in your life?
- Where do you want to be in five years? Do you need to make any changes right now to get yourself on that path?
- What is the biggest setback you’ve faced when pursuing a goal, and how did you overcome it?
- Have you ever failed at something very important? How did you deal with it?
- What would you say is your biggest accomplishment to date, and why are you so proud of it?
- What does success mean to you? Is it mainly financial? Does it have to do with prestige or status? Or is it more emotional?
- What would you say is your biggest goal in life? Is there anything I can do as your friend to help you achieve it?

Section 6 of 8:

Deep Questions to Ask About Life and the World

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Ask these questions to learn more about your friend’s unique worldview. Everyone sees the world in different ways, so it can be super fascinating to explore the similarities and differences in your and your friend's perspectives. Ask your friend these deep questions about the world and life, in general, to get an interesting, philosophical convo going.
- Do you think society is headed in the right or wrong direction? Why do you think this?
- If you could change one thing about modern-day culture, what would it be?
- Do you think social media is mainly a positive thing or a negative thing?
- Would you ever want to be famous, and do you think fame is a good thing?
- Do you think it’s important to travel a lot in life?
- If you had to list your top 3 core values, what would they be?
- Do you consider yourself an optimist, pessimist, or realist?
- Do you share your worldview with your family, or did you end up developing a different perspective from them?
- What role does religion or spirituality play in your life?
- Do you believe in the supernatural at all, or do you only believe in material reality?
- What do you think happens after we die?
- If you could find out the day you were going to die in advance, would you want to know?
- How do you want to be remembered by the people who knew you after you’re gone?
- What do you think your main purpose in life is?
- Where does your sense of morality and ethics come from?
- What do you think it means to be a good person?
- Do you believe in karma?
- Do you think it’s important to have a similar worldview to someone if you want to be their friend or romantic partner?