192 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.

One 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).

How well do you know your best friend?

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

two men talking Questions to Ask Your Best Friend

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.

192 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?

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?

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?

women sitting on ground talking Questions to Ask Your Best Friend

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?

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 a 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?

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

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?

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?

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?

Sexual Questions to Ask Your Friend

Check out these questions about sex to ask your best friend:

1. Who was the first person you ever had sex with?

2. What's the best sex you've ever had?

3. If you could have sex with one famous person or celebrity, who would it be?

4. What's the most times you've had sex in one day?

5. Have you ever had really bad sex?

6. Have you ever had a one-night stand?

7. Are you a morning or night person when it comes to sex?

8. Have you ever “faked” it?

9. If you had to give up sex or lose your taste buds, which would you choose?

10. Is there something sexual you or your partner want to try but the other doesn't want to?

11. Do you ever have sex when you didn't feel like it?

12. What's the funniest thing that's ever happened during sex?

13. How often would you prefer to have sex?

14. What's the longest time you've gone without sex?

15. Have you ever said someone else's name during sex?

16. Do you use a vibrator?

17. Do you talk during sex?

18. Where is the strangest place you've had sex?

19. How old were you when you lost your virginity?

20. Do you fantasize about other people during sex?

21. Have you ever walked in on your parents having sex?

22. Have you ever sent someone sexy photos of yourself?

23. Do you prefer the lights on or off during sex?

24. Are you happy with your body and showing it during sex?

25. As an adult, what's the longest time you've gone without sex?

Personal Questions to Ask Your Best Friend

Here are some personal questions that you might feel comfortable asking a friend you've known for a long time.

1. Do you ever wish you had different parents?

2. What is your biggest life regret?

3. Have you ever cheated on someone?

4. What recreational drugs have you used in the past?

5. What kind of friend do you think you are to others?

6. What do you feel the most ashamed of?

7. Have you ever been arrested for anything?

8. Are you afraid of dying?

9. If you could change one thing about your body, what would it be?

10. Do you have a bad habit you wish you could change?

11. Have you ever cheated on a test?

12. Do you wonder if there really is a God?

13. If you had one day left to live, how would you spend it?

14. Is there someone in your life you really dislike?

15. If you could have a do-over in one part of your life, what would it be?

16. What do you think are your best and worst qualities?

17. What is something no one else knows about you?

18. Do you think of yourself as more selfless or selfish?

19. Who is the most important person in your life?

20. If you could trade lives with someone, who would it be?

21. Have you ever shoplifted?

22. What is your guilty pleasure?

23. Are you still holding a grudge against someone?

24. Do you have a favorite sibling?

25. If I asked you for an honest opinion that might hurt me, would you tell me the truth?

Random Questions to Ask Your Best Friend

Here are some interesting and fun random questions to ask to get to know your best friend even better.

1. If you were an animal, what kind of animal would you be?

2. If you could visit any period in history, when and where would it be?

3. Do you think there's an alternative reality?

4. Would you ever consider running for public office?

5. If you could only eat salty snacks or sweet snacks for the rest of your life, which would you choose?

6. What actor would you like to play the starring role of your life?

7. Who should play me (as your best friend)?

8. What is your favorite season of the year?

9. If you could keep just five of your possessions, what would they be?

10. What is your best birthday memory?

11. What was one of your favorite gifts as a child?

12. If you were traveling by yourself, where would you go and what would you do?

13. What is something irrational that you've wanted to do but never done?

14. What magical power would you like to possess?

15. Where are you when you feel the most safe and comfortable?

16. Would you donate an organ to someone you love?

17. If you had to wear one outfit every day for the rest of your life, what would it be?

18. How long do you want live?

19. How do you want to be remembered by your friends and family?

20. Who is your favorite fictional character and why?

21. What songs meant the most to you during high school?

22. If you could go back and tell your childhood self something, what would it be?

23. What behaviors do you despise in another person?

24. If you could have chosen your own name, what would it be?

25. If you could be a professional in one sport, which one would you choose?

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Spicy Questions to Ask Your Best Friend

1. What's the most outrageous lie you've ever told to get out of a date?

2. Have you ever had a crush on a friend's parent?

3. What's the most embarrassing thing you've ever done to impress a crush?

4. Have you ever been caught in a compromising situation?

5. What's the most scandalous thing you've ever done at a party?

6. If you could erase one past relationship from your memory, which would it be and why?

7. Have you ever been caught cheating on a test or in a game?

8. What's the most outrageous thing you've done to get someone's attention?

9. What's the riskiest thing you've ever done on a first date?

10. What's the most seductive thing you've ever worn to a party?

11. Have you ever been caught in a lie by someone important to you?

12. What's the craziest moment of jealousy you've had?

13. What's the most embarrassing thing you've ever done at a job?

14. What unconventional job would you consider taking if you had to?

15. Have you ever created a fake social media account? If so, why?

16. Tell me about a ridiculous bet you took and lost.

17. Describe a spontaneous and weird thing you've done out of sheer boredom.

Final Thoughts

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 175 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.