Conversation Starters

115 Funny, Deep, and Juicy Questions to Ask Your Best Friend

Meaningful conversations with your best friend are essential for nurturing and strengthening your bond. These exchanges offer opportunities for connection, laughter, and understanding.

 In this guide, we’ll explore various categories of questions to ask your best friend, ranging from lighthearted and funny to deep and thought-provoking.

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Whether you’re seeking moments of joy or moments of introspection, these questions will help spark engaging conversations and deepen your friendship.

Questions to Ask Your Best Friend

Light-hearted and Funny Questions to Ask Your Best Friend

  1. If you could only eat one food for the rest of your life, what would it be?
  1. What’s the silliest thing you’ve ever done as a kid?
  1. If you could switch lives with any fictional character for a day, who would it be?
  1. What’s your favorite thing to do to unwind after a long day?
  1. If you could have any superpower, what would it be and why?
  1. What’s the most embarrassing thing that’s ever happened to you in public?
  1. If you could travel anywhere in the world right now, where would you go?
  1. What’s the funniest movie or TV show you’ve ever watched?
  1. If you could only listen to one song for the rest of your life, what would it be?
  1. What’s your favorite childhood memory?
  1. If you were stranded on a desert island, what three things would you bring with you?
  1. What’s the weirdest dream you’ve ever had?
  1. If you could meet any historical figure, who would it be and why?
  1. What’s the most adventurous thing you’ve ever done?
  1. If you could have any talent, what would it be?
  1. What’s your favorite joke?
  1. If you could go back in time and change one thing, what would it be?
  1. What’s the best piece of advice you’ve ever received?
  1. What’s your favorite way to spend a lazy Sunday?
  1. If you could be any animal for a day, which one would you choose?
  1. What’s your guilty pleasure?
  1. If you could have dinner with any celebrity, who would it be?
  1. What’s the weirdest food combination you’ve ever tried?
  1. What’s your favorite board game or card game?
  1. If you could invent a new holiday, what would it be and how would you celebrate it?

Funny and Weird Questions to Ask Your Best Friends

115 questions to ask your best friend friendship so true
  1. If you could only communicate in animal noises for a day, which animal would you choose?
  1. Would you rather fight a hundred duck-sized horses or one horse-sized duck?
  1. What’s the most ridiculous thing you’ve ever done for a dare?
  1. If you were a vegetable, which one would you be and why?
  1. If you could only eat one condiment for the rest of your life, which one would it be?
  1. What’s the weirdest dream you’ve ever had that still makes you laugh?
  1. If you could swap lives with a cartoon character for a week, who would it be and why?
  1. Would you rather have the ability to talk to animals or speak all foreign languages fluently?
  1. If you could teleport anywhere in the world right now, where would you go and why?
  1. What’s the most embarrassing thing that’s ever happened to you in front of a crush?
  1. If you could only wear one color for the rest of your life, what would it be?
  1. Would you rather have spaghetti for hair or have to sneeze every time someone says your name?
  1. If you could have any mythical creature as a pet, which one would you choose?
  1. What’s the strangest food combination you’ve ever tried and actually liked?
  1. If you could swap lives with a famous historical figure for a day, who would it be and what would you do?
  1. Would you rather have a permanently itchy nose or constantly feel like you need to sneeze but never be able to?
  1. If you were a superhero, what would your superpower be and what would your superhero name be?
  1. What’s the most absurd thing you’ve ever Googled out of curiosity?
  1. Would you rather have a dragon or a unicorn as a pet?
  1. If you could only eat one type of candy for the rest of your life, what would it be?
  1. What’s the most bizarre talent you wish you had?
  1. If you could shrink down to the size of a bug, what insect would you ride around on?
  1. Would you rather have the ability to fly but only at a walking pace or be able to teleport but only to places you’ve already been?
  1. If you could only speak in rhymes for a day, how would you handle it?
  1. What’s the weirdest thing you’ve ever found at the bottom of your bag or purse?

Deep and Thought-provoking Questions to Ask Your Best Friends

115 Deep and Thought provoking Questions to Ask Your Best Friends so true
  1. What is your biggest fear, and what do you think it says about you?
  1. If you could change one thing about the world, what would it be and why?
  1. What does happiness mean to you, and do you think you’ve found it?
  1. What is the most significant lesson you’ve learned from a difficult experience?
  1. Do you believe in destiny or that we create our own paths in life?
  1. What is your idea of a fulfilling and meaningful life?
  1. How do you define success, and do you feel like you’ve achieved it?
  1. What role do you think forgiveness plays in personal growth and healing?
  1. If you could go back in time and give your younger self one piece of advice, what would it be?
  1. What is your greatest strength, and how has it helped you overcome challenges?
  1. Do you believe in the concept of soulmates, and if so, do you think you’ve found yours?
  1. What is your biggest regret, and what have you learned from it?
  1. How do you think your upbringing has influenced the person you are today?
  1. What is the most valuable lesson you’ve learned from a friendship or relationship?
  1. How do you cope with uncertainty and change in your life?
  1. What do you think is the purpose or meaning of life?
  1. How do you handle conflicts and disagreements in your relationships?
  1. What does it mean to live authentically, and how do you strive to do so?
  1. What is the most important quality you look for in a friend or partner?
  1. How do you define love, and what does it mean to you?
  1. What role do you think vulnerability plays in building connections with others?
  1. What are your thoughts on the concept of fate versus free will?
  1. How do you find balance between pursuing your dreams and maintaining relationships?
  1. What do you think is the key to maintaining a strong and lasting friendship?
  1. If you could ask the universe one question and receive an answer, what would you ask?

Juicy and Spicy Questions to Ask Your Best Friends:

  1. What is your wildest fantasy, and have you ever acted on it?
  1. Have you ever had a crush on someone your best friend was dating?
  1. What’s the most scandalous thing you’ve ever done on a date?
  1. Have you ever had a one-night stand, and if so, what was it like?
  1. What’s the craziest place you’ve ever hooked up with someone?
  1. Have you ever had a romantic encounter with someone much older or younger than you?
  1. What’s the kinkiest thing you’ve ever done in the bedroom?
  1. Have you ever experimented with role-playing or BDSM?
  1. What’s your opinion on open relationships or polyamory?
  1. Have you ever been caught doing something naughty in public?
  1. What’s the most embarrassing thing you’ve ever said during s*ex?
  1. Have you ever had a crush on a teacher or authority figure?
  1. What’s your guilty pleasure when it comes to adult entertainment?
  1. Have you ever sent a racy photo to someone, and if so, did it end up in the wrong hands?
  1. What’s the most outrageous pickup line you’ve ever used or heard?
  1. Have you ever had a friends-with-benefits arrangement, and did it work out?
  1. What’s your opinion on s*ex on the first date?
  1. Have you ever had a secret affair or fling with someone you shouldn’t have?
  1. What’s the most unconventional place you’ve ever had s*ex?
  1. Have you ever had a threesome, and if so, how was the experience?
  1. What’s the most embarrassing thing that’s ever happened to you during a hookup?
  1. Have you ever had a crush on a celebrity, and if so, who?
  1. What’s the most risqué thing you’ve ever done to spice up your love life?
  1. Have you ever had a crush on someone of the same gender?
  1. What’s the most adventurous s*exual experience you’ve ever had?

Questions to Ask Your Best Friend About Yourself

  1. What’s the earliest memory you have of us together?
  1. What’s one thing you admire most about me?
  1. Can you recall the moment when you realized we were going to be best friends?
  1. What’s my biggest strength, in your opinion?
  1. What’s one habit or quirk of mine that you find endearing?
  1. If I were a character in a book or movie, who would I be and why?
  1. What’s one thing I always talk about or am passionate about?
  1. What’s my favorite type of music or artist?
  1. Can you remember a time when I surprised you in a positive way?
  1. What’s one of my goals or dreams that you know about?
  1. What’s one piece of advice I’ve given you that has stuck with you?
  1. When do you think I’m at my happiest?
  1. What’s one thing I always say I want to do but haven’t done yet?
  1. What’s my go-to comfort food?
  2. If I were stranded on a desert island, what’s one thing you think I would want to have with me?

These questions offer an opportunity to deepen your bond with your best friend through candid and open conversations.

 Remember, laughter and honesty are the keys to building a strong and lasting friendship. Embrace the opportunity to explore new topics and share experiences together.

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