100 Intriguing Questions To Ask Your Best Friend

When was the last time you just sat and talked to your best friend about anything and everything?

Are there ever times when you’re not sure what to talk about, so you fill the awkward silence with music or a video – or small talk?

Maybe you and your best friend don’t need much of a prompt to get a conversation going.

queOne of you comments on the other’s sweater, and you’re off to a running start — jumping merrily from one tangent to the next.

And then there are friends who are fine with amicable silence but who also take the time to answer your questions thoughtfully. And one question could be enough for an hour’s conversation (or more).

Whatever default conversation settings you have, if you’re wondering what questions to ask your best friend, try the ones listed below. You might be surprised by what you’ll learn about each other.

As an added bonus, you’ll probably get a better idea of what to get this friend for Christmas (or an upcoming birthday).

Quick note: Having good communication on a date and in a relationship is an important skill to develop. To learn more, check out this course that is helping couples learn healthy communication skills.

How well do you know your best friend?

If you look at your best friend sometimes and think, “How well do you know me?” or “What do I not know about you that I should?” it can’t hurt to ask some personal questions.

This isn’t a first date, after all, and you didn’t just meet your BFF in an elevator. Besties have certain privileges when it comes to getting personal.

You probably have some idea as to the conversation territory your best friend would rather avoid, but you can still learn plenty about each other with the questions that follow.

100 Questions to Ask Your Best Friend

Deep Questions to Ask Your Best Friend

Pick from any of these 25 personal deep questions to ask your friend:

1. Whom do you look up to the most — and what qualities in that person do you want to see in yourself?

2. What do you most want to accomplish in your life?

3. What do you see in yourself that you dislike when you see it in other people?

4. What do you see in yourself that you admire when you see it in other people?

5. What challenges do you most want to overcome?

6. Do you ever wish you’d handled a situation differently? How do you wish you’d handled it?

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7. What is your biggest fear?

8. When you’re sad or upset about something, how do you like to be comforted? Or would you rather be left alone to process it?

9. Tell me about a favorite memory.

10. What do you believe will happen to you when you die?

11. If someone you cared about voted for a candidate you strongly dislike, would you forgive that person?

12. If you won half a billion dollars from the lottery (assume you bought a ticket), what would you do first?

13. Who was the last person to make you cry? What do you wish this person would have said to you?

two men talking Questions to Ask Your Best Friend

14. If money were no object, what one thing would you buy for yourself to make life easier or more fun?

15. If you could be close friends with any celebrity, who would it be?

16. Where do you hope to be three to five years from now? How about ten years?

17. If your next home could have one thing of your choice that your current home does not have, what would that thing be?

18. What are you most proud of? Or when did you last feel overwhelmed with pride in yourself or in someone else?

19. What is your biggest challenge right now (and is there anything I can do to help)?

20. What family member do you feel closest to?

21. If you could travel to anywhere in the world, and money was no object, tell me where you’d go and how you’d get there.

22. What book has had the biggest impact on you?

23. What relationship shaped you the most when you were growing up?

24. Do you want (more) kids? How many?

25. If you could earn any amount as your monthly income, what would that be and why?

Funny Questions to Ask Your Best Friend

Choose from any of these 25 fun questions to ask your friends :

1. What is your most embarrassing memory?

2. If you could wake up with a completely different permanent hair color — any color — what would it be?

3. If you had to choose between living in a fully modernized castle (air conditioning, adequate heating, plumbing, wifi, etc.) by a waterfront and living in a spacious, light-filled, and beautifully furnished downtown apartment, so you could walk everywhere, which would you choose?

4. If you could go on a date – or just out to dinner — with a celebrity, who would it be?

5. If you could play a friendly prank on any actor, whom would you prank and how?

6. What do you do when no one else is around that you’d rather most people didn’t know about?

7. What’s one thing about you that you’d never mention on a first date?

8. If you could eat one thing for dinner every day, what would it be?

9. If you could have dessert every day, but it had to be same thing (every day), what would it be?

10. If you had to get a tattoo, what would you get and where would it go?

11. Have you ever given a gift that the recipient hated (or didn’t know what to do with)?

12. What was the last (or most memorable) gift you’ve received that you ended up donating or giving to someone else?

13. If you had to get either a dog or a cat, which would it be? And do you have a name already picked out?

14. Do you believe in the existence of aliens — specifically intelligent life on other planets?

15. If you were elected president of the United States, and if the current president made a solemn vow to do anything you wanted him to do, what would you tell him? And would that thing be televised?

16. If you were to go (back) to college, what major would you choose?

17. If you could only listen to one type of music (rock, alternative, jazz, classical, etc.) for the rest of your life, what would it be?

18. When you just want something easy and comforting to make for dinner, what do you choose?

19. Has anyone ever mistaken you for someone else — and did they do something either of you regret?

20. If you could be driven around everywhere by a chauffeur, what vehicle would you want that chauffeur to drive?

21. If you had to eat the same thing for lunch every day, what would it be?

22. If you woke up as one of your favorite cartoon characters, who would you be?

23. If you had to wake up to someone or something licking your face, what would you see when you opened your eyes?

24. If someone were to tell you, “Congratulations, you just won a lifetime supply of ______!” what would you want to hear in that blank?

25. How would you react if I told you I was going to shave my head and rent my scalp out for advertising?

Weird Questions to Ask Your Best Friend

Check out these 25 weird questions to ask your best friend:

1. If you could pick an age and just stay that age for as long as you’re alive, what age would you be? And yes, I mean any age.

2. If you could choose between living for 1,000 years and living for only 50, which would you choose — and why?

3. If your significant other lost his/her job and decided to just not work anymore, what would you do?

women sitting on ground talking Questions to Ask Your Best Friend

4. What is your weirdest fantasy, and what would you do if it came true?

5. What did you dream about last night? Or what is the weirdest, most memorable dream you’ve ever had?

6. If you had three wishes, what would you wish for?

7. What did you learn to do before your 18th birthday that most people you’ve met don’t know how to do?

8. If you could live someone else’s life for a day, whose life would you pick?

9. If you were a four-course meal (salad/appetizer, pasta/soup, entree, dessert), what would you be?

10. If you could live in a different time period, what would it be and why?

11. If you could instantly speak any second (or third, etc.) language as fluently as your first, what would that language be and why?

12. What unusual talent or skill do you wish you had that you don’t?

13. What talent or skill do you have that you wish paid really well?

14, If you had the chance to play a role in a movie with one of your favorite actors, but it involved a kissing scene, would you say “Yes.” Or would you rather just sit down with this actor and chat for half an hour over coffee (or something else)?

15. A courier has just arrived with news that you are related to royalty, and they want you to drop everything and head to the royal family’s country to be recognized. What would go through your head while you were being told all this, and would you go?

16. If you had to be stranded on a desert island with a celebrity, who would it be?

17. If you had to choose between the celebrity and a robot or your favorite book, what would you choose?

18. You’ve just won a home renovation package, but you have to choose between a complete reflooring and repainting (inside and out) of your home or upgrades for all your appliances, plus an extra (like a Nespresso machine or an above-the-range microwave). What would you choose?

19. Before you head out one day, your S.O. tells you he’ll / she’ll have a surprise waiting for you when you get back. What do you hope it will be?

20. If I have good news and bad news to share, which do you want to hear first?

21. You just received a gift that reminds you of the best gift you’ve ever received — but this gift came from someone you hardly know, and that someone winked at you when handing you the gift. What do you do?

22. It’s St. Patrick’s Day, and someone pinches you for not wearing green. What do you do?

23. It’s Christmas, and an attractive stranger walks up to you with a sprig of mistletoe and asks for a kiss — “just a little one <wink, wink>.” What do you do?

24. It’s Halloween and your S.O. wants you both to dress up like Vision and Wanda/Scarlet Witch from Avengers: Infinity War and go to a party. You had other plans for the evening. What do you do?

25. Your S.O. bought a new perfume/cologne, and you think it smells terrible. What do you say?

Questions to Ask Your Best Friend about Yourself

Pick from any of these 25 questions to ask your friends about yourself:

1. If I told you one day that I had a superpower that made it unnecessary for me to pay rent (or pay for much of anything), what would you do?

2. Where would you like to see me in five years?

3. If I won the lottery and was suddenly a half-billionaire, what do you think I’d do first?

4. If I were to tell you I had a year to live, what would you do? Or what would you hope I did?

5. If someone who knew us both asked you whether I’d rather have a million dollars or a cool superpower, what would you tell them?

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6. Do you see us doing something together within the next five years? And if so, what do you see us doing?

7. If I could change one thing about my life, what do you think it would be?

8. If I were a musical instrument, which would I be?

9. I just spent way too much money on a new exercise machine, because it has all the features I want, and I didn’t want to wait for a sale. What would you tell me?

10. If you came over, and I was in a terrible mood and not really up for conversation, what would you do?

11. If I started dressing exactly like you – even trying to wear the same outfit every day – and then started talking and acting like you, what would you say to me?

12. If I lashed out at you, but you knew that the person I was really angry with was someone else — and if that someone else was also important to you — how would you handle it?

13. If you saw me stress-eating or drinking more alcohol than you knew I could handle, what would you do?

14. If I was going to repaint my living room, and I showed you a sample of a color — and you hated it — would you tell me? Or would you pretend to like it?

15. If I was going on a date, and I showed you the outfit I was planning to wear, and you thought it was unflattering, what would you do?

two men sitting on bench talking Questions to Ask Your Best Friend

16. My S.O. just left me for someone else, and he accidentally left his credit card in my apartment. You walk in and find me holding it and looking as though I’m plotting something. What do you do?

17. What was your first or most memorable thought when you first met me?

18. When we met, what made you think I’d be a good friend?

19. What is your favorite thing about my home/living space? What is your least favorite thing about it?

20. What is the first thing you usually notice about me when we meet (for coffee, chat, movies, etc.)?

21. Is there anything more I could do to make sure you know how much I appreciate having you as a friend?

22. Is there anything you’ve been dying to suggest to me but haven’t dared because you were nervous about how I’d react? What would make it easier to tell me?

23. When was the last time you tried to talk to me about something that was bothering you, and I did or said something that made you decide not to?

24. How would you finish this sentence if you were directing these words at me: “I wholeheartedly believe that you would make a great ______” or “I hope with all my heart that you finally _______”?

25. Based on what you know about me, what do you think would make my life easier or more fun?

More Related Articles:

31 Good Things To Talk About With Anyone

20 Signs Of Fake Friends And How To Find Real Friends

50 Best Friend Tag Questions And How to Play

Was this fun — and challenging?

That was the plan.

With some of the difficult questions to ask friends listed above, you might learn more about yourself than you do about your best friend. With others, you might both reveal something the other hadn’t so much as guessed.

That’s the risk you take when you make it your goal to know your best friend better.

You may uncover things that test your relationship. But until you’re willing to take that risk – so you can prove that your friendship is more important to you than your differences – you can’t really call each other best friends, anyway.

Take the leap. Be the friend you hope everyone has.

Now that you have 100 good questions to ask your best friend, see how many of them you can both answer. If it helps, print out the list, so you can cross off each question as you answer it.

Or keep these best friend questions handy by saving this article to the Pocket app on your phone or tablet.

If you’ve found value in this article on questions to ask your friend, please share it to help others learn more about their best friends and about each other.

And may your gratitude and sense of humor influence everything else you do today.

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