65 Fun & Deep Questions to Ask Your Best Friend and Bond Like Real BFFs

Your best friend may be your ride or die, but do you know them as well as you think you do? Here are 65 questions to ask your best friend!

Even though you and your friend are BFFs, there may be things you still haven’t shared or asked each other. Maybe you’re too shy or worried about what they’ll think. But if you don’t ask these questions to ask your best friend, you will never know.

There’s nothing wrong with asking funny, awkward, or controversial questions to learn more about your best friend. If anything, it helps you become even better friends.

They are your best friend. They’ve seen you at your best and at your, well, not so best. Yet, through it all, they stuck by you. So ask them these questions and get to know them even better! [Read: How to be a good friend – 49 traits & friend codes that define a real pal]

How conversations deepen friendship

When it comes to your best friend, more often than not, you probably share the same opinions about certain topics. However, there might be a thing or two you both don’t see eye to eye on. Even though you think you know everything about your best friend, do you really?

Holding conversations with friends allows you to understand each other on a deeper level and ultimately brings the two of you closer. Because we are social beings, close friendships grow our sense of belonging as well as purpose. This increases our happiness and overall quality of life!

We all want to have an open and honest relationship with the people around us. It is part of what makes us human. We crave honest connection and open communication because it fulfills aspects of our emotional needs.

Questions to ask your best friend that’ll reveal it all

Sometimes, even when we spend a lot of time together, we don’t know the deeper side of our very best friend. There are tons of things you probably want to know about them and vice versa.

If you think you know everything there is to know about your best friend and think you both see eye to eye on all different subjects, ask them these questions. You might be surprised by what you find out. [Read: Fun things to do with your best friend & create lasting memories]

Here are 65 questions to ask your best friend that ranges from playful to serious. Prepare to have some interesting conversations!

1. What do you think about aliens?

Do they exist? What do you think they look like? Your BFF probably has a couple of thoughts on it. [Read: 25 personal questions to ask your best friend and bond like a real BFF]

2. What animal would you be if you could choose?

Bunny? Dog? Fish? It’s a silly question, but the funny thing is we’ve all thought about it.

If you really want to get to know them even better, this question to ask your best friend will reveal their true character. Or, if you think you know them better than anyone else, see if your guess about their spirit animal is the same as theirs!

3. What’s your favorite holiday?

Everyone has a favorite. Christmas? Thanksgiving? Easter? You can only pick one!

4. What era would you live in if you could choose?

The rockin’ 80’s? The classic 50’s? The Medieval era? What time period would they love to explore if they could?

5. You have $10,000—what would you do with it?

Are they going to spend it all? Save it? What would they do with all that cash?

Are they charitable enough to donate a large portion of it, or are they smart enough to invest it? See, these questions to ask your best friend actually can help you find out a lot about them!

6. Are you a dog or cat person?

There’s always one that we like over the other. Make them pick one, no matter how hard the decision is to make! [Read: Fur baby – Why millennials are choosing puppies over babies]

7. Do you like eating breakfast foods for dinner?

You’re either hardcore for breakfast food at dinner, or you find it to be an abomination. There isn’t much room for an in-between. What does your best friend think?

8. Dessert or a fancy drink?

This one is really more for fun than anything else. But nonetheless, it can tell you a little something you may not have known before. It can show how much they value a great drink or a delicious dessert when they’re dining out.

9. Would you rather go skydiving or cliff jumping?

Although this isn’t the most telling question, it could help you see the difference in how adventurous the two of you are. An added bonus: it might even stir up a new adventure for both of you to take on together.

10. If you could only use one kind of cosmetic product for the rest of your life, what would you choose?

Not only is this a fun one to think about, but it can actually reveal a lot about your best friend. It might even show an insecurity of theirs that you never knew about before.

11. What’s more relaxing to you: a day at the spa or a night out with your friends?

This differs from person to person. But if you like the spa and they like a night out, trying to relax together might be a little difficult.

12. What foreign language do you want to learn?

Is there a language they’re curious about? Do you share the same passion for languages?

13. Bars or clubs?

They are similar, but definitely not the same. One is perfect for those who want to sit and chat over a few drinks, while the other is better suited for the party animal who prefers dancing to the beating tunes over holding a conversation.

Could the two of you have fun out during the night or do you both want something different when heading out? [Read: The girl’s guide to strip clubs and female strippers]

14. If you had to eat only one food for the rest of your life, what would it be?

Either they’ll choose their favorite food ever or think about the nutritional aspect of eating only one food forever. Regardless, you can determine if you both think alike in terms of choosing favorites over logic.

15. If you were stranded on a deserted island, what’s the one thing you would want with you?

Would they bring something practical, or their favorite non-practical item? It’s surprising what people value over different things.

16. Would you rather be rich or famous?

This is one of those personal questions to ask your best friend that may seem like a surface-level question, but actually, it can tell you a lot about someone. Why did they answer the way they did? [Read: Would you rather questions to leave you thinking]

17. If you were famous, what do you think it would be for?

The answer here might shock you. Some would say acting, others singing, and some might say writing a book or being a weather person. The options are endless.

18. Are you a lucky person?

Do things always happen to work out in their favor? Would they consider themselves lucky?

They have you as a best friend, so no doubt they’re a lucky person to some extent!

19. What book changed you?

Have they read a book that really changed their outlook on life? Which book was it?

20. Is there a smell that makes you think of me?

Let’s just hope they don’t say dog poo or dirty socks!

21. What’s your favorite memory of us?

There’s always one memory that your BFF holds close to their heart. This gives the two of you an opportunity to reminisce over good memories together.

22. What’s your dream job?

We all have a dream job. But do you know what your BFF’s is? News anchor? Restaurant owner? Dog rescuer? [Read: 30 all-around good questions to ask people for a better connection]

23. Would you give anyone the password to your phone or social media accounts?

Is your best friend super private? Or are they an open book? And if anyone, who would they trust with such a thing?

24. What are your top three pet peeves?

We can all be annoyed by small things. Maybe it’s the way someone chews their food or coughs without covering their mouth. What are their peeves?

This question to ask your best friend is actually useful for you because you can find out if you’ve accidentally been doing something that really gets on their nerves!

25. What’s your ideal place to live?

You might not know if your best friend is happy living where they are, or if they’re secretly dying to live elsewhere.

This could show how much the two of you think alike or show how different the two of you really see your lives playing out. They probably have one place that they’ve been dying to explore. Maybe you can make it a reality together.

26. Would you rather live to old age and have an average life, or live a short life but full of adventures?

This one will be surprising no matter which direction it goes because of the reasons associated with it. Maybe you guys think completely differently, or maybe you two are best friends because you see eye-to-eye on things like this.

27. What is something you have always wanted to do but are afraid you’ll never be able to do?

This question is a doozy. Fearing that you won’t be able to accomplish a goal and fulfill your dream is terrifying, and admitting you think you are capable of failure is hard.

But opening up to a friend like this can help release a lot of pressure you put on yourself. [Read: How to be fearless – 18 ways to set aside fear & live like a champion]

28. Would we be friends if we met earlier?

What do you guys think? Would you? Five years ago, you may have been a completely different person before you met them.

29. What will we do when we get old?

This always brings laughs, thinking about when you two will be old. Just imagine all the trouble you two could cause in the nursing home!

30. What are three things we 100% agree on?

You’re not always going to like the opinion of your BFF, but there are things that you both definitely agree on. This might be a good question to whip out if any of these other questions reveal a huge difference in opinions. [Read: Unique traits that make a person trustworthy]

31. When was a time you were really disappointed in me?

It’s a hard question to ask and even harder to hear the answer. But this can help you grow as a person and as friends.

32. Why do we get along so well?

There’s something that connects you, what is it? Every pair of best friends has something that brings them closer together.

33. What words would you use to describe me?

This is personal in the sense that you get to see how your friend views you. And who knows, maybe you’ll find something out about yourself.

34. How do you think I would describe you?

Similarly to how they would describe you, asking them how they think you see them can be very insightful. Not only can this expose how you both truly feel, but it can clear up any confusion.

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

This is such an important question. Whether it is their mom, sibling, child, or even pet, this lets you know who you should maybe get to know better.

36. What’s your earliest memory?

It’s hard to think about, but everyone has memories of their very early childhood, no matter how big or small or fuzzy. Some people remember things back to their toddler years, others not until their elementary-school years or later.

Your first memory is something ingrained in your mind forever. And it sure is a sweet and touching thing to share with someone so close to you.

37. What was your childhood like?

Someone’s childhood may seem like a long-forgotten memory, but that can be a time that truly molds someone.

You could learn why your best friend does certain things, goes certain places, or acts a specific way just by hearing a few throwback stories. [Read: The types of friends everyone needs in their life]

38. Are you close with your parents?

A person’s relationship with their parents affects so many aspects of their life. You may have had this friend for years, but they never mentioned their dad. Or maybe they live with their mom, but you’ve never met her. Learning why will help you get to know your best friend that much better.

39. Do you see your grandparents a lot?

Some people have never even met their grandparents. Others might have only a few memories with them. And some may have been raised by them. Asking your friends about them can open that relationship to more possibilities.

40. Who is your oldest friend?

And are you still just as close as you used to be? Yes, this answer could be you.

But if it isn’t, this can open the door for your best friend to reconnect with someone. It can also let you into why they lost touch and help you prevent that from happening.

41. What do you think about soulmates?

Do they believe in soulmates? Are you two soulmates? [Read: Twin flame – What it is, 41 signs & ways to recognize your twin soul]

42. Who was your first love and what happened?

Depending on how long you have known your best friend, this question can really make you understand them and their dating habits a lot better.

Our first love is a starting point and kicks off our attitude toward dating in the future, so learning this can help you give them advice too. [Read: How your first love affects your future relationships]

43. Do you want to have kids?

It may sound so far away, but the future hits you fast. Wanting to have kids is a huge decision. And it is no one’s right to try to change your mind one way or the other.

But sharing your opinions and reasoning can be useful for you both. Not only can it bond you, but it can open your eyes to another point of view.

44. If you had to pick someone in your life right now to have a child with who would you pick and why?

This can be a great question to ask your best friend, especially if they are single. Maybe the person they truly care for is right in front of them and they never realized it.

45. Who last made you cry?

You’ll probably want to go smack that person in the face.

46. Have you ever cheated on someone?

There is a lot to say for someone that has cheated on their partner. And as much as your personal feelings may be swayed, knowing this sort of thing about your best friend is important.

You don’t hide any part of yourself from your best friend. You let it all out, the good and the bad, and love them anyway.

47. What do you feel the most guilty about?

This is very telling. Looking back, a lot of people have guilt for different things. And talking to someone, especially your best friend, about it can help let that guilt wash away.

48. If you had to choose between money or love, which would you choose?

This speaks volumes about a person. Most people are going to choose love—mainly because if you say money you’re probably considered selfish.

However, there are people out there who value security and living well over living with love in their life. Find out if you and your bestie have this one in common!

49. What is the biggest lie you’ve ever told?

This is not something you ask to hold something against your best friend but to learn why they told that lie. Were they a dumb kid at the time? Were they protecting someone? Or were they protecting themselves? [Read: 50 hardest would you rather questions that have no right answers!]

50. What’s your biggest fear?

This can be a very deep and personal question. At first, you might think of sharks or snakes or spiders, but really the deeper fears are quite a bit darker than that.

Sharing these things with your BFF is important to really know each other and maybe even help each other face that fear.

51. Do you have any regrets?

There may be something they’ve been dying to talk about. Why not share this with your best friend?

Regrets can be very powerful. You can regret not going to university. You can regret being a bully in grade school. And you can regret getting married.

Sharing these things with someone close, who you trust, can help you realize those choices were necessary to get you where you are.

52. What’s your biggest flaw?

It’s a hard question to answer! No one wants to think about their flaws, but your best friend will be open and honest with you. [Read: Do you REALLY know them? 20 fun questions to ask a friend]

53. Do you have high self-esteem?

We all struggle with insecurities now and then. And knowing that you and your best friend share those struggles can bring you even closer. Not to mention you can lift each other’s spirits when those struggles get you down. 

54. What is something no one knows about you?

This can be something like your friend keeps a journal, love to paint, or put a child up for adoption. This can get really deep so be prepared.

55. How much do you care about what other people think?

To some extent, everyone cares what others think. But how much your friend cares about the opinions of others lets you know how much your friend ignores and how much the thoughts of others really affect their attitude and outlook. [Read: 26 whys & ways to surround yourself with positive people & remodel Your life]

56. Are you afraid of dying?

You might think, DUH! Who isn’t? But depending on someone’s spiritual or religious beliefs the answer can drastically change.

57. Are you religious?

This can be an iffy subject for some, but it is nice to know how you and your best friend agree or differ on these big topics.

Not only does it help from a practical sense when it comes to planning events, but also so you understand their beliefs and perhaps become more well-rounded and open-minded.

58. How do you feel about helping the homeless?

This is a coin toss per person. Some feel helping is vital to bring down homeless rates while others believe help is actually enabling it. Do you and your best friend have the same thoughts about this hugely controversial topic?

59. What is your stance on abortion?

This can be a touchy subject for many people, especially since the overturning of Roe v Wade, but it shouldn’t be with your best friend.

It’s an important topic that too many people don’t talk about enough. It also can show you a lot about your best friend’s personal views and choices.

60. Do you ever think the world will be at peace?

Get them to think a little harder about the world today and see if you both are optimistic or think the world is doomed to suffer forever.

61. What do you think could help the world be more peaceful?

This is a great follow-up to the above question. What do they think can help make the world a better place? Maybe one of their ideas is something you’ve never even thought of. [Read: Simple ways to inspire the people around you]

62. If you could change one thing about society, what would it be?

This really brings to light the different issues out there today and which your best friend sees as the most important. Are you two on the same page with this?

63. If you had one day left to live, would you spend it with family or go on an adventure?

Some people would want to relax with loved ones. Find out if your best friend is thinking like you or if the two of you are on opposite ends of the spectrum.

64. When you pass away, what would you want people to remember you for?

Maybe it’s something they’ve already done or maybe it’s something they still want to accomplish. Either way, this gives insight as to what they think the most defining thing in their life is/will be and if it’s in sync with what you want out of life. [Read: What is my purpose in life – 33 secrets to find meaning when you feel lost]

65. What’s the one thing on your bucket list that you absolutely MUST complete?

Everybody has that ONE thing they want to accomplish before their days are over. Do you think alike? Is your bucket list the same or similar to your best friend’s?

What to remember when asking your friend questions

When asking your best friend these questions—especially the serious or controversial ones—you must remember that everyone is different for a reason. Our differences are what bring us together.

Your best friend should feel safe from your judgments just as you should feel safe from theirs. If there is an opinion of theirs that you disagree with, that doesn’t have to be the end of the friendship. Instead, use your difference in opinions to strengthen your bond together.

These questions to ask your best friend will not only bring you closer but they will help you understand each other better. This way, your friendship can grow even stronger.

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