100 Juicy Questions to Ask Your BFF

cheerful teenage girls lying together at park
Interesting Questions to Ask Your Best Friend Maskot - Getty Images


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Think back: how did you first bond with your ride-or-die? Maybe you met through a book club and both loved all the same parts of Normal People. It could be that you made small talk, discovered you both love to cook, and have been trying out recipes together ever since. Or maybe you met at a playdate and became devoted parent friends.

Want to enrich your friendship even further? It’s easy — asking your best friend the right questions can deepen your connection. “Asking open-ended questions helps to develop platonic desire,” says Danielle Bayard Jackson, a friendship coach and the author of Fighting for Our Friendships. “People want to know that they’re wanted and that you’re reaching out to them. Asking these questions shows caring, because it says, ‘I want to learn about you and understand you.’”

Discovering your friend’s likes, dislikes, feelings and goals cements honesty, too. “Authentic conversations between friends build safety, trust, and respect,” says Noah Kass, DSW, LCSW, a psychotherapist. “Remind yourself that being honest gives your friend permission to be honest,” Kass adds. “In friendship, vulnerability is contagious and powerful.”

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Kass suggests that some open-ended phrases in conversation that can foster closeness include:

  • What did that feel like?

  • How did you know?

  • Tell me about it.

  • What was that like?

  • What were you thinking?

As for fun topics to ask your bud about? We’ve got you covered! Next night at your favorite Italian restaurant, order that pasta and pizza to share, and kick off the convo with 100 great questions for best friends. Get ready to learn a lot, and have fun!

Questions About Their Childhood

Your friend’s beginnings shaped the person they are today.

  • What’s the first memory you have of the world?

  • Did you have an imaginary friend when you were little? Spill the beans on your relationship!

  • What about a special stuffed toy? What was its name, and why was it your favorite?

  • When you were between 5 and 10 years old, what did you want to be when you grew up?

  • What was your all-time favorite Halloween costume?

  • What Christmas or birthday gift did you want SO much, but didn’t get? (You could always buy it for them now as an amazing sentimental surprise!)

  • Who was your favorite teacher? Why did this teacher inspire you?

  • What do you remember most about your best friend as a kid?

  • What was your favorite childhood movie? Do you still comfort-watch it?

  • What song reminds you most of being a kid?

Questions About Their Likes

The things that please them make them so interesting!

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  • What is your all-time favorite item of clothing? Why do you love it?

  • Describe your perfect Saturday night. (Let’s make it happen!)

  • Which country would you most love to visit?

  • What famous person would you most like to meet? Why?

  • Which ice cream flavor does not get enough love?

  • What’s your favorite season? Why do you love it?

  • You get a no-strings $1000 shopping spree. What are you buying?

  • What’s your dream car?

  • What’s your fave guilty pleasure reality show?

  • What is the most beautiful sight you’ve ever seen?

Questions About Their Dislikes

What they think is in bad taste can show they’ve got good taste!

  • What food have you pretended to like but secretly hate?

  • What is the worst fashion trend of all time?

  • What habit do you have that you’re dying to break?

  • What’s the most boring movie you ever sat through?

  • What was the worst day of your life like?

  • What do you dislike the most–talking on the phone, texting, or Zooming?

  • What was your least favorite subject in school?

  • Which sport is simply not for you?

  • What’s your least favorite day of the week? Why?

  • Do you prefer being too cold to being too hot, or vice versa?

cheerful woman taking selfie with man
Klaus Vedfelt - Getty Images

Questions About Their Love Life

…that you haven’t already talked about over and over.

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  • Who was your very first kiss? Where was it? How was it? Give up the deets!

  • Who was your celebrity crush as a tween or teen?

  • Describe your very first boyfriend/girlfriend. Do you have positive memories, or wish you’d learned the ropes of love with someone else?

  • Do you believe in love at first sight?

  • Could you forgive infidelity?

  • What’s the one thing you’ve always wanted your partner to do for you, but you’ve been afraid to ask for?

  • What did your parents’ relationship teach you about the kind of love you want in your life?

  • What has been your biggest heartbreak ever? What did you learn from it?

  • What’s the biggest risk you’ve ever taken for love?

  • Have you ever broken up with someone in a way you now regret?

Questions About Their Family

Your bestie’s roots are fascinating and formative.

  • Would you ever trace your DNA ancestry? Why or why not?

  • How do you think you take after your parents?

  • Describe your favorite family vacation growing up–why was it so special?

  • Which member of your family do you feel most comfortable with?

  • What was the best family holiday celebration you ever had?

  • What family tradition will you carry on forever?

  • If you could have dinner with any of your ancestors, who would that be and why?

  • How did you get your first and middle names? Who in your family named you?

  • What family meal from your childhood makes you feel happy and nostalgic? (I’ll make it with you!)

  • What lesson did you learn from your family that helps you to this day?

Questions That Cover How Fabulous They Are

(Let them know you want them to brag!)

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  • What is your proudest career achievement so far?

  • What part of your body do you love the most? Or is it the whole gorgeous package?

  • What three qualities do you admire most about yourself?

  • What’s your hidden talent?

  • What is the best compliment you’ve ever received?

  • Which movie star should play you on the big screen?

  • What’s the most selfless thing you've ever done?

  • What makes you feel powerful?

  • What’s the nicest thing you’ve ever done for another person?

  • What is the toughest challenge you’ve ever met?

friends using smartphone at home
Igor Alecsander - Getty Images

Questions About Their Goals for the Future

It’s great to know where they want to go.

  • What do you want your life to look like in ten years?

  • How many kids do you want?

  • Would you like to be famous?

  • Are you into manifesting?

  • What’s your biggest dream to make a reality?

  • What’s your perfect place to live look like?

  • What’s one thing you’re determined to accomplish this year?

  • Would you ever move to a totally new city and start over from scratch?

  • What hobby do you want to take up next?

  • What would you like your legacy to be?

Important Questions About Their Values

These questions get at the core of who they are.

  • What mistake have you made that you think you learned the most from?

  • What matters more to you–money or peace of mind?

  • What’s your prized possession?

  • Do you think it’s ever OK to break a promise?

  • Do you prefer playing it safe or taking a risk?

  • Have you ever held a grudge?

  • Do you think you’re easily influenced by other people?

  • What do you think is the worst quality a person can have?

  • How much do you worry about climate change?

  • Do you think people are basically good or basically bad?

Questions To Get To Know Them Even Better

These revelations just might make your friend even cooler (if that’s even possible!).

  • Do you believe that rejection can sometimes be protection? Have you ever experienced this?

  • What mistake have you made that you think you learned the most from?

  • What superpower would you want, and how would you use it?

  • What’s the most magical thing you’ve ever experienced?

  • What language would you love to learn?

  • Which song do you have stuck in your brain right now?

  • What job might you like to have if you weren’t pursuing your current career?

  • What’s the scariest thing you’ve ever done willingly? (Bonus points for skydiving or swimming with sharks.)

  • Do you have any superstitions? (Or maybe a lucky pair of socks?)

  • How closely do you really follow your zodiac sign?

Questions About Your Friendship

Feel their feelings, and your friendship can become a true kinship.

  • Do you remember the first thing you said to me the day we met?

  • What quality do you prize most in me as a best friend?

  • Do you have a secret you want to share with me that you haven’t yet? (You know I won’t tell…)

  • What is the best advice I ever gave you?

  • What’s one thing I can do to be even more supportive of you?

  • What would you change about me if you could? No worries, I WANT to know!

  • Why do you think you’re such a good friend to me?

  • Do you think we are more alike than we are opposite? How, either way?

  • What do you think is the most fun thing we’ve ever done together?

  • What do you think we’ll be doing for fun together when we’re 90?

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