When you have a special bond with someone, you want to know as much as you can about each other. Which is why we have gathered all the best random and juicy questions to ask your best friend to for fun conversions.
Now go ahead and browse through to find your favorite.
Questions to Ask Your Best Friend
What is the best compliment you’ve ever received?
What mistake have you made that you think you learned the most from?
What’s your favorite memory of our friendship as a whole?
How do you think you take after your parents?
Which sport is simply not for you?
Favorite memory of our friendship in the last year?
Do you believe that rejection can sometimes be protection? Have you ever experienced this?
What superpower would you want, and how would you use it?
When you were between 5 and 10 years old, what did you want to be when you grew up?
What makes you feel powerful?
What do you think is the worst quality a person can have?
What does love mean to you?
What is your proudest career achievement so far?
Do you struggle with anxiety?
If you already have kids, what’s your favorite aspect of parenthood? Least favorite?
Do you think people are basically good or basically bad?
Could you forgive infidelity?
Have you ever broken up with someone in a way you now regret?
What do you consider to be your top coping mechanism?
What’s the nicest thing you’ve ever done for another person?
What do you want people to know about you?
Who was your very first kiss? Where was it? How was it? Give up the deets!
What’s the scariest thing you’ve ever done willingly?
Who was your celebrity crush as a tween or teen?
Which ice cream flavor does not get enough love?
When you can’t sleep at night, what are you usually thinking about?
Who do you see as the earliest positive influence in your life?
You get a no-strings $1000 shopping spree. What are you buying?
What do you want your life to look like in ten years?
What was your least favorite subject in school?
Do you think we are more alike than we are opposite? How, either way?
What do you remember most about your best friend as a kid?
Have you ever kept anything from me? If so, why?
Who was your favorite teacher? Why did this teacher inspire you?
What is the most beautiful sight you’ve ever seen?
What is your love language?
Do you have a secret you want to share with me that you haven’t yet?
What job might you like to have if you weren’t pursuing your current career?
Do you think it’s ever OK to break a promise?
What’s your fave guilty pleasure reality show?
Describe your very first boyfriend/girlfriend. Do you have positive memories, or wish you’d learned the ropes of love with someone else?
What language would you love to learn?
What song reminds you most of being a kid?
How can I better show my appreciation for our friendship?
Who do you feel most inspired by?
What has been your biggest heartbreak ever? What did you learn from it?
What is your all-time favorite item of clothing? Why do you love it?
How did you get your first and middle names? Who in your family named you?
What’s the one thing you’ve always wanted your partner to do for you, but you’ve been afraid to ask for?
How closely do you really follow your zodiac sign?
If you could have dinner with anyone, dead or alive, who would it be?
What hobby do you want to take up next?
What was the best family holiday celebration you ever had?
If you didn’t have your current job, what would you be doing instead?
What’s the biggest risk you’ve ever taken for love?
What’s your biggest dream to make a reality?
What is the toughest challenge you’ve ever met?
Which song do you have stuck in your brain right now?
Which member of your family do you feel most comfortable with?
Do you prefer playing it safe or taking a risk?
What Christmas or birthday gift did you want SO much, but didn’t get?
Would you like to be famous?
If you could live in any decade, which one would you choose?
Do you have a secret talent I don’t know about?
What would you like your legacy to be?
What was your favorite childhood movie? Do you still comfort-watch it?
Do you have any regrets? What are they?
What’s one thing you’re determined to accomplish this year?
What do you consider to be your most embarrassing moment?
Have you ever held a grudge?
What’s the best gift you’ve ever received?
If your partner didn’t like me, what would you do?
What’s your least favorite day of the week? Why?
Would you ever move to a totally new city and start over from scratch?
Which country would you most love to visit?
If you could have dinner with any of your ancestors, who would that be and why?
What habit do you have that you’re dying to break?
What about a special stuffed toy? What was its name, and why was it your favorite?
What would you change about me if you could? No worries, I WANT to know!
Would you ever trace your DNA ancestry? Why or why not?
What family meal from your childhood makes you feel happy and nostalgic? (I’ll make it with you!)
What quality do you prize most in me as a best friend?
Describe your perfect Saturday night.
Are you into manifesting?
What matters more to you–money or peace of mind?
What’s the most boring movie you ever sat through?
What was the hardest moment of your life?
What’s the best place you’ve ever visited? Wha did you love about it?
Can you tell me your life story in three minutes?
What do you appreciate the most about out friendship?
What family tradition will you carry on forever?
When you’re upset, how do you typically like to be comforted?
Do you remember the first thing you said to me the day we met?
What is the worst fashion trend of all time?
What’s the most selfless thing you’ve ever done?
If you had a day when you could absolutely anything you wanted, what would you do?
What’s your dream car?
What lesson did you learn from your family that helps you to this day?
Do you believe in love at first sight?
Do you think you’re easily influenced by other people?
Why do you think you’re such a good friend to me?
How many kids do you want?
Describe your favorite family vacation growing up–why was it so special?
What food have you pretended to like but secretly hate?
What did your parents’ relationship teach you about the kind of love you want in your life?
What’s your favorite season? Why do you love it?
What do you think we’ll be doing for fun together when we’re 90?
Which movie star should play you on the big screen?
What was the worst day of your life like?
What’s the first memory you have of the world?
When do you feel the most fulfilled?
What part of your body do you love the most? Or is it the whole gorgeous package?
Did you have an imaginary friend when you were little? Spill the beans on your relationship!
What makes your life feel purposeful?
What’s your prized possession?
What do you most look forward to doing with me in the future?
Of all the things in your life, what are you most grateful for?
What do you think is the most fun thing we’ve ever done together?
What would your dream vacation with me look like?
What do you dislike the most–talking on the phone, texting, or Zooming?
What are some of the things you still want to accomplish in your life?
Would you ever want to be famous? If so, in what way?
What is the best advice I ever gave you?
What’s one thing I can do to be even more supportive of you?
What three qualities do you admire most about yourself?
How much do you worry about climate change?
In general, are you happy?
What’s your hidden talent?
What famous person would you most like to meet? Why?
What’s the most magical thing you’ve ever experienced?
Do you want kids? Why or why not?
What was your all-time favorite Halloween costume?
What’s your perfect place to live look like?
Do you prefer being too cold to being too hot, or vice versa?
Do you have any superstitions?
So that is it for our list of Questions to Ask Your Best Friend. We hope you found the perfect one for you!
If you like these, you might also want to check out our other lists of Daily Journal Prompts, Deep Questions and Questions to Ask Your Boyfriend.
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About the Author
Laynni Locke
I am Laynni Locke, a Canadian writer, reader and traveller with a passion for sharing life’s moments on social media. Keeping friends and family in the loop of our lives though photos and videos has become an essential activity for most.
And it doesn’t matter if you are travelling, celebrating a special occasion or just appreciating day-to-day life, when you take that perfect photo you are going to need the perfect caption or quote before you share it. Which is why we started Routinely Shares, providing comprehensive lists of quotes and captions to cover every occasion, adventure or loved one.
With extensive experience as a travel writer, social media specialist and grant writer, I have made it my mission to curate the best and easiest to use lists for your next post.