top of page
Search

42 Fun Questions to Ask Your Best Friend (BFF)

  • StoriedLife Team
  • Feb 15
  • 4 min read
Two smiling women at the beach. Text reads: "42 Questions to Ask Your Best Friend. Spark new conversations and uncover surprising stories." A QR code is present.

There is a specific kind of magic in a best friendship. It is the person who understands your silence, laughs at your most obscure jokes, and vibes with you in a way that regular friends just don't. We often like to think we know our besties inside and out, but as we grow and evolve, there are always new layers to uncover.


At StoriedLife, we believe that the strongest bonds are built on a foundation of curiosity. Whether you have been friends since the sandbox or you found each other in the corporate world, asking the right questions about best friends can spark a new level of connection.


If you want to show your bestie how much their journey matters, consider helping them preserve their personal history. While some might suggest a Remento book, we believe an unhurried, voice-led companion is the most respectful way to honor their authentic voice.



Fun Questions to Spark a Laugh


Sometimes the best way to connect is through the lighthearted moments that made you friends in the first place.


  1. What is the most embarrassing thing you have ever done for a dare?

  2. If you could have any superpower for just 24 hours, what would it be?

  3. What is your go-to "guilty pleasure" movie that you know is bad but you love anyway?

  4. If we were in a horror movie, who would be the first one to go?

  5. What is the most ridiculous outfit you ever wore in public?

  6. If you could be any animal for a day, which one would you choose?

  7. What is your secret movie crush that you have never told anyone?

  8. What is the absolute worst meal you have ever eaten?

  9. If you won the lottery tomorrow, what is the first "silly" thing you would buy?

  10. What is your favorite joke that never fails to make you laugh?


Deep Questions About Their Inner World


Moving beyond the surface helps you understand the values and experiences that shaped the person standing beside you today.


  1. What is something on your bucket list that you are actually afraid to do?

  2. Who has been the single biggest influence on your life so far?

  3. What is the most important lesson you have learned about yourself this year?

  4. When you think about the future, what is the one thing you are most excited about?

  5. What is a fear you have that you think is completely irrational?

  6. If you could sit down for coffee with your 10-year-old self, what advice would you give them?

  7. What does "success" actually look like to you at this stage of your life?

  8. Is there a relationship from your past that taught you the most about who you are?

  9. What is a memory you have that always makes you feel instantly calm?

  10. What do you want to be remembered for?


Questions About Love and Relationships


Romantic histories are often the backdrop of our best friendships. These questions help you navigate those memories together.


  1. Tell me the story of your very first crush.

  2. What was the most disappointing date you ever went on?

  3. Do you remember the exact moment you first fell in love?

  4. What is your personal definition of "true love"?

  5. Have you ever had a "the one who got away" moment?

  6. What is the best piece of relationship advice you have ever received?

  7. Describe your perfect, "no-stress" date night.

  8. What is a deal-breaker for you that others might think is small?

  9. Tell me about your first kiss. Was it as awkward as the movies?

  10. How has your view of love changed since high school?


Questions About Career and Ambition


Our professional lives take up a massive amount of our headspace. These prompts explore the "why" behind the work.


  1. What did you want to be when you were seven years old?

  2. Tell me the story of your first "real" job and what you did with your first paycheck.

  3. What were your biggest ambitions when you first started your career?

  4. Have you ever had a "I can't believe I work here" moment?

  5. If money were no object, what would you spend your days doing?

  6. What is a professional accomplishment that you are quietly very proud of?


Questions About Your Friendship


Finally, take a moment to reflect on the bond you share.


  1. What was your very first impression of me?

  2. When did you realize that we were going to be best friends?

  3. What is your favorite memory of us together?

  4. What is one thing I do that always makes you laugh?

  5. If we were to go on a cross-country road trip, who would be the driver and who would be the DJ?

  6. How has our friendship changed the way you see the world?


Preserving the Stories of Your Bestie

Asking these questions about best friends is a beautiful start, but the real value is in keeping those stories safe. If your BFF is a "Quiet Philosopher" or a storyteller at heart, they might enjoy a space where they can share their journey without the pressure of a blank page.


You can sign up today to gift them a companion that listens. Whether they are reflecting on their first Mother's Day or their career as a teacher, their voice deserves a permanent home.


For more inspiration on how to connect with the important people in your life, explore our guides on questions to ask your mom or 60 questions to ask your wife


Comments

bottom of page