255+ Deep & Fun Questions to Ask Your Best Friend

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Plus, learn how to have deep, meaningful conversations with your BFF
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Are you ready to schedule a bonding session with your bestie and need some good questions to spark great conversations? Well, you’ve come to the right place! We’ve put together a list of over 255 deep , funny , and downright random questions to help you get to know them better and make your friendship even stronger. Plus, we spoke with expert therapists and psychologists to learn how to have even better conversations and connect with your BFF in a healthy way.

Top Questions to Ask Your Best Friend

  • What do you think you’ll be like in old age?
  • What do you think it means to be a good friend?
  • What would your perfect day look like?
  • What’s your least favorite emotion?
  • Did you enjoy growing up in your hometown?
  • How do you know what's right and wrong?
  • Would you sacrifice money for freedom?
Section 1 of 12:

Deep Questions to Ask Your Best Friend about Themselves

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  1. “Make sure that the time you spend together feels rich in terms of the conversation,” recommends licensed clinical psychologist Chloe Carmichael, PhD. Having a deep conversation is a great way to make your time richer. Try one of these deep questions to really understand how they see the world:
    • What brings you the most happiness in life right now?
    • If you could erase one memory from your mind, which would you pick?
    • What’s one piece of advice you’d give to your younger self?
    • What thing keeps you going on hard days?
    • What’s the worst decision you’ve ever made?
    • What do you think you’ll be like in old age?
    • Do you have any regrets? If so, what are they?
    • If this was our last conversation, what would you want me to never forget?
    • When do you feel the most beautiful?
    • Is there a specific event in your past that you think was a major turning point for you?
    • Which of your personality traits are you most proud of?
    • Do you consider yourself an extrovert or an introvert?
    • What do you think is your best quality?
    • How would you describe your personal style?
    • If you could stay one age forever, what age would you choose?
    • What instrument would you like to learn how to play?
    • What’s the first thing you do when you wake up in the morning?
    • If you had to change your name, what would your new one be?
    • If you could have one superpower, which would it be?
    • Do you feel like you act differently when you’re by yourself versus when you’re with a group of people?
    • Do you think there’s something that people misunderstand about you?
    • What's the first thing you notice when you meet a person?
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Section 2 of 12:

Questions to Ask Your Best Friend about Friendship

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  1. Get a sense of what they want in a friend with questions about friendship. Dr. Carmichael defines a friend as “somebody who's reliable, somebody you can count on, somebody who genuinely celebrates when things go well in your life.” But your BFF might have different ideas. Figure out what they want in a friend with these questions:
    • What’s something you’d consider unforgivable?
    • Have you ever gone through a friendship breakup? What caused it?
    • When did you feel most betrayed by a friend? How did you deal with it?
    • Is there anything you would change about our friendship?
    • Is there anything I do that makes you feel especially supported?
    • What’s more important in a friendship, loyalty or honesty?
    • What recent experience made you feel closer to me?
    • What was your impression of me when we first met?
    • Do you tend to befriend people who are similar to you, or do you think opposites attract?
    • What do you think it means to be a good friend?
    • Do you believe in having one best friend?
    • What do you value most in friends?
    • Do you think friends or family are more important?
    • What does your ideal friend weekend look like?
    • Is there anything I can do to show my appreciation for your friendship that I do not already do?
    • Have you ever stopped talking to a friend?
    • Is there a childhood friend that you’re still in touch with today? How has your relationship evolved?
    • How long has your oldest friend been in your life?
    • What’s your favorite memory from our friendship?
    • If you could have a celeb as your BFF, who would it be?
    • Who is the first person you text when you get good news? Bad news?
    • How do you prefer to be comforted when you're upset?
Section 3 of 12:

Questions to Ask Your Best Friend about Likes & Dislikes

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  1. According to clinical psychologist Allison Broennimann, PhD, “It's hard to have a nourishing friendship without taking the time to build it.” Try out these interesting questions to go beyond the surface about your best friend’s likes and dislikes and build your friendship:
    • What do you wish you did more of?
    • If you had to curate the soundtrack to your life, what songs would be on there?
    • What do you love most about life?
    • What would you most like to do right this second?
    • What luxury item would you splurge on?
    • If you could only eat pizza, wings or burgers for the rest of your life, which would you choose?
    • Do you prefer sunny or rainy days?
    • What’s your favorite comfort food?
    • What’s your least favorite emotion?
    • What is something that makes you really angry?
    • Would you rather live by the beach or up in the mountains?
    • What type of food do you absolutely hate?
    • What’s the worst book you ever read all the way through?
    • Do you prefer sweats or dressing up?
    • What song could you listen to on repeat for the rest of your life?
    • Who is your favorite musician or band?
    • Would you rather drink coffee or tea for the rest of your life?
    • What is your comfort movie?
    • What’s your least favorite type of music?
    • If you could only eat at one restaurant for the rest of your life, what restaurant do you choose?
    • Do you prefer to stay in or go out on the weekend?
    • What hobby would you like to try out?
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Section 4 of 12:

Questions to Ask Your Best Friend about Family & Childhood

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  1. Ask about your BFF’s background to know where they come from. Our family relationships and childhood experiences have a huge impact on our lives and how we think about the world. [1] Ask your best friend a few of these questions to get a better sense of how their family and childhood experiences have shaped who they are:
    • What was the most memorable vacation you went on as a child?
    • If you had to describe your family in one sentence, what would it be?
    • Were your parents strict, or were they more laid-back?
    • Which of your parents’ traits do you admire the most?
    • What gives you a sense of family or makes you feel like you belong?
    • What’s the first memory you have of the world?
    • What's a toy you had growing up that you wish you still had?
    • Are you closer to one parent than the other?
    • Which family member do you look up to the most?
    • Did you enjoy growing up in your hometown?
    • What is your favorite childhood memory?
    • If you could change one thing from your past, what would it be?
    • What’s the most challenging part about spending time away from your family?
    • Do you ever wish you had more or fewer siblings?
    • Have you ever looked into your family lineage? Do you know anything about your ancestry?
    • Does anyone in your family have a nickname for you?
    • Were you a rebel or an obedient kid growing up?
    • What’s your favorite story your grandparents have told you?
    • Who gives the best gifts in your family?
    • Were there any family traditions that you looked forward to every year when you were a kid?
    • Out of all your family members, who are you the closest with?
    • If you can give your parents one thing in the world, what would it be?
Section 5 of 12:

Questions to Ask Your Best Friend about Values

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  1. It’s not a big deal if you have different values and faiths, though. According to licensed marriage and family therapist Lia Huynh, LMFT, “There is so much to like and enjoy about a person aside from your faith [and] beliefs.” But asking questions like the ones below can help you get a better understanding of where they’re coming from:
    • Do you believe in God or some higher power?
    • What do you believe happens when we die?
    • What do you believe is the purpose of your life?
    • Would you convert to a different religion for your life partner?
    • What is the most awe-inspiring thing you've ever seen or experienced?
    • How much of a role does chance or randomness play in what happens?
    • Do you believe humans can ever truly live in harmony with nature?
    • Have your beliefs stayed the same throughout most of your life, or have they changed a lot?
    • How do you know what's right and wrong?
    • What do you think is the worst quality a person can have?
    • Do you think people are basically good or basically bad?
    • Have you ever participated in a protest? Which one(s)?
    • What are the most important values that you have always stood by?
    • What’s a value you’re unwilling to compromise on?
    • What, according to you, should be your spirit animal?
    • If you knew it was your last day on Earth, what would you make sure to do?
    • If you could ask God one question, what would you ask?
    • What’s the biggest leap of faith you’ve taken?
    • What is your life motto or mantra?
    • Are there any lessons or values from your childhood that you still carry with you today?
    • Do you consider yourself a religious or spiritual person?
    • If you had to fight for one global cause for the rest of your life, which would it be?
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Section 6 of 12:

Questions to Ask Your Best Friend about Career & Goals

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  1. Find out what they want to do with their life with probing questions. “A big part of friendship is feeling supportive of each other,” Dr. Carmichael tells us. Asking a friend about their goals shows you care and gives you an idea of how to support them in the future. Learn how you can help encourage your friends to achieve their goals with a few of these questions:
    • What would you do with your life if money was not a concern?
    • Who is the best boss you've ever had? What do you think made them such a good leader?
    • What does success mean to you?
    • In one year, what do you want in your life that you don't have now?
    • What would you like your legacy to be?
    • Would you sacrifice money for freedom?
    • Would you ever move to a totally new city and start over from scratch?
    • What would you say is your biggest goal in life? Is there anything I can do as your friend to help you achieve it?
    • What is the biggest setback you’ve faced when pursuing a goal, and how did you overcome it?
    • What was your dream job when you were growing up?
    • Are you happy in your current career path?
    • What's one thing about the future that scares you?
    • If you were given a chance to choose an alternative career, what would you choose?
    • Have you ever had “impostor syndrome”? What did you do about it?
    • Do you prefer working remotely or in an office?
    • What are some goals you'd like to accomplish by the time you're 50?
    • Do you keep working despite feeling unwell?
    • If you were elected as POTUS, what would be your first to-do?
    • What motivates you to go after your goals?
    • What’s most important to you: work life or personal life?
    • What does your dream future look like?
    • What career path do you see yourself taking in the future?
Section 7 of 12:

Dating & Relationship Questions to Ask Your Best Friend

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  1. When you ask your friend questions about love, dating, and relationships, it can help you better understand what they’re looking for in life. It can also give you clues about what makes them feel emotionally supported in your friendship. Try a few of these questions to better understand their emotional needs:
    • Do you think there is one person out there that each of us is meant to be with?
    • Do you believe in love at first sight?
    • What has been your biggest heartbreak ever? What did you learn from it?
    • What’s your love language?
    • Do you fall in love quickly, or does it take a while for you to fall in love with someone?
    • Which do you think is more important, physical compatibility or emotional compatibility?
    • What kind of person do you picture yourself ending up with?
    • What’s the biggest risk you’ve ever taken for love?
    • Could you forgive infidelity?
    • What's the most petty dealbreaker that will instantly turn you off of a potential love interest?
    • If your exes were all stuck in a room together, what would they say about you?
    • Have you ever been in love?
    • Would you uproot and relocate your life for someone you love?
    • How do you get over heartbreak?
    • What is the longest relationship you’ve been in?
    • Why do you think people cheat on their partners?
    • What are your top 3 most essential qualities in a romantic partner?
    • What’s the best advice an older person has ever given you about relationships?
    • Do you think people fall in love because the right person shows up or because the time in their life is right?
    • Have your parents or family ever not liked your significant other?
    • What was the best date you've ever been on? The worst?
    • What is your idea of the perfect proposal?
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Section 8 of 12:

Funny Questions to Ask Your Best Friend

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  1. Lighten the mood with a few funny questions. Laughing together is a great way to strengthen your bond with your best friend. Plus, it’s good for your health! [2] Try a few of these funny questions to give your bestie a chuckle and brighten their day:
    • Would you rather fight a human-sized duck or the number of regular-sized ducks equal to the weight of an average human?
    • Why do round pizzas come in square boxes?
    • Would rather be 3 feet shorter or 3 feet taller?
    • What celebrity would you challenge to a fist fight?
    • How many animal sounds can you make?
    • What’s the most creative insult you can think of right now?
    • What is one super-specific museum you would visit?
    • What’s the worst song ever written?
    • What’s the dumbest thing you’ve ever looked up online?
    • What's a word that you pronounced incorrectly for years before anyone told you?
    • If you could understand what animals are saying, which one do you think would be the rudest?
    • What's the reason for saying “after dark” when it's actually really after light?
    • What is the funniest thing you've ever seen in another person's house?
    • What's your least favorite planet?
    • What do you think would be the worst "buy one, get one free" sale of all time?
    • What is the funniest name you have ever heard in real life?
    • What do you think the first person to milk a cow was actually trying to do?
    • What's the worst tagline you can think of for a wart removal cream company?
    • Is a hot dog a sandwich?
    • What is the worst possible name you might give your child?
    • Who actually tests the specific dog food when they say that it has a new and improved flavor?
    • What's the funniest joke you've ever heard?
    • What’s your Spice Girls stage name?
    • What’s the funniest Wi-Fi name you’ve ever seen?
    • What meme best represents your life?
    • Do you wash your feet in the shower?
    • If a word was misspelled in the dictionary, how would anyone know?
    • Do fortune cookie predictions have a time limit?
Section 9 of 12:

Weird & Random Questions to Ask Your Best Friend

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  1. Start a really unusual conversation with a weird, random question. Random or weird questions might make your BFF laugh, but they can also spark a truly unique and interesting conversation. Try one of these cool questions to catch your friend by surprise and maybe start a truly one-of-a-kind conversation:
    • What’s your favorite smell?
    • Have you ever eaten a bug?
    • How would you survive a zombie apocalypse?
    • What conspiracy theories are totally real?
    • What’s the weirdest thing you own?
    • Do you believe in ghosts?
    • If a song played every time you entered a room, what would it be?
    • What’s a podcast you don't tell anyone you listen to?
    • What’s the weirdest fact you know?
    • What do you do when nobody is watching?
    • What kind of noises did dinosaurs make?
    • Would a mermaid give birth or lay eggs?
    • If you could be the main character of any movie, what movie would it be?
    • Do you know how to fold a fitted sheet?
    • How many ants would it take to lift an elephant?
    • How would you show that you were from the future if you were transported 200 years into the past with no clothing or anything else?
    • What's the weirdest thing you've given someone as a gift?
    • Have you ever accidentally glued your hands together when doing a craft project?
    • What's the first thing you wash in the shower?
    • If you could put one condiment inside your belly button, what would it be and why?
    • If you had to lose your hands or your feet, which would you choose?
    • If you could be any object, which would you be and why?
    • If you could travel back in time to any historical event, which would it be?
    • Do you think you’d get along with a clone of yourself?
    • In your opinion, which color has the worst personality?
    • Have you ever eaten something off the floor?
    • Is there a limit to how smart someone can be?
    • Do you eat or drink soup?
    • How many pairs of underwear do you own?
    • If you’re bald, what hair color gets listed on your driver’s license?
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Section 10 of 12:

Juicy & Spicy Questions to Ask Your Best Friend

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  1. Get to know your BFF on a deeper level with juicy and spicy questions. Sometimes you have to ask your friend a really juicy question to take your friendship to the next level . Here are a few spicy questions to help you shake things up and really get to know your best friend:
    • What’s the cringiest thing you’ve ever posted on social media?
    • How many people have you kissed?
    • What’s the most scandalous piece of clothing you own?
    • Have you ever been in a love triangle?
    • Have you ever practiced kissing your hand?
    • What’s the best piece of gossip you’ve ever received?
    • Have you ever cheated on anyone?
    • Do you think you’re a good kisser?
    • What’s the most attractive physical feature?
    • What’s an embarrassing thing you’ve done and never told anyone about?
    • What’s the weirdest thing you’ve done in public?
    • Have you ever had a sex dream about a celebrity? Which one?
    • What's the craziest thing you've ever done?
    • How many exes' numbers are still in your phone?
    • What’s the worst thing you’ve done to get out of trouble?
    • Have you ever gone skinny dipping?
    • Do any types of conversations make you uncomfortable?
    • When was the last time you were jealous, and why?
    • What's your relationship really like with your parents?
    • If you found money on the ground, would you keep it or look for the owner?
    • Who was your first celebrity crush?
    • Would you like to be married or be in a live-in relationship in the future?
Section 11 of 12:

Questions to Ask a New Friend

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  1. Make a new friend your BFF by getting to know them better. Sometimes, you just feel like you really connect with a person. But you can’t just rush into calling them your bestie. Get to know who they really are with a few of these questions:
    • What are you most proud of?
    • What habit do you have that you’re dying to break?
    • If you had to pack up and move to another country tomorrow, where would you go?
    • What's one book that changed your life?
    • Do you have a hidden talent?
    • What's your latest guilty pleasure?
    • Do you consider yourself introspective?
    • What do you think it means to be healthy?
    • Have you ever had a moment of deja vu?
    • Is it easy or difficult for you to accept help from people?
    • Do you believe in aliens or life on other planets?
    • What does getting out of your comfort zone look like for you?
    • When was the last time you had a regret?
    • Are there any particular tech or social media habits that you find bothersome?
    • What do you love most about life?
    • Do you enjoy being somewhere no one else knows you?
    • Where is one place you’ve always dreamed of going?
    • What's your biggest pet peeve?
    • If you could have dinner with anyone, dead or alive, who would it be?
    • If you won the lottery, what would you do with the money?
    • If you could have any talent, what would you choose?
    • What would your perfect day look like?
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Section 12 of 12:

Having Great Conversations with Your Best Friend

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  1. Dr. Carmichael explains, “When you know that you're going to be going into a situation where… there'll be a conversation, you can do a little bit of simple, even kind of fun, prep work.” So, make a mental note of a few questions you’d like to ask your friend.
    • For example, ask something like, “If you could go back and relive 6th grade, what would you do differently?
    • Open-ended questions encourage your friend to give answers that are longer than 1-2 words.
    • Asking better questions lets the other person know you’re interested in hearing more about their thoughts and feelings.
  2. 2
    Use active listening and ask for clarification if you need it. When you use active listening skills, you show your friend that you’re engaged and interested in what they’re saying. There are a few different ways to actively listen, including: [3]
    • Limit distractions and give your friend your complete attention.
    • Avoid interrupting them. Instead, wait for a natural break to respond.
    • Use engaged body language like eye contact, nodding, facing the other person, and leaning slightly toward them.
    • Avoid crossing your arms and legs to keep your body language open and relaxed.
  3. 3
    Show genuine interest without any judgment. Even if you disagree with your friend’s opinions or perspective, it’s important to understand what they’re saying and accept it. [4] Dr. Carmichael also recommends that you show your friend that you value them by thanking them for opening up to you. This shows them you want to get closer and build your friendship.
    • When you talk to a friend , avoid making counterarguments or thinking about what you’re going to say while they’re still speaking.
    • Keep any advice to yourself unless they ask for it. Unwanted advice can be annoying and seem a little judge-y, like they need your help.
  4. Wanting to share your thoughts and feelings with your best friend is perfectly normal. According to Dr. Carmichael, “Another big marker of friendship is trust and intimacy, and really feeling known and seen by the other person. And so for some people, that means that they want to share some of the more personal, sensitive information about themselves.”
    • Being vulnerable and opening up can feel scary because you don’t know how the other person will react.
    • But opening up to your friends can lead to better conversations that bring you closer together and help them understand how you feel about things. [5]
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      References

      1. ↑ https://www.psychologytoday.com/us/blog/fixing-families/201903/4-key-ways-your-childhood-shapes-you
      2. ↑ https://www.helpguide.org/mental-health/wellbeing/laughter-is-the-best-medicine
      3. ↑ https://ggia.berkeley.edu/practice/active_listening
      4. ↑ https://ggia.berkeley.edu/practice/active_listening
      5. ↑ https://loveyourmindtoday.org/finding-support/opening-up-to-friends-family

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