If you’re keen to get to know your bestie better, here are some fun and deep questions to ask your best friend. You might be shocked at their answers!
If you want to get to know your best friend better than ever and keep the conversation ticking along nicely, you need things to talk about. So, why not come up with a list of questions to ask your best friend, ranging from fun to deep?
After all, you might have known your friend for years and years, but there are still things to discover. There is no end to the bond between best friends. [Read: 71 friendly, funny questions to get to know someone in a happy way]
Why you should ask your best friend deep questions
It might seem obvious. Deep questions bring people closer together. Sharing personal feelings, experiences, and fears enhances your trust and helps you understand one another better.
If you have a best friend that you never ask deep questions, it does not mean the friendship is doomed to fail, but it can plateau and remain on a surface level.
With the help of deep BFF questions and the answers to those questions, you can share so much more with each other and form an unbreakable bond. Or, of course, strengthen the one you already have. [Read: 15 signs of a best friend that prove you’ll never find someone better]
The best deep questions to ask your best friend
Deep BFF questions can range anywhere from your five-year plan to your greatest fear and beyond. And when your best friend is involved, there is really no limit.
Whether you are having a deep conversation or just randomly asking some of these questions while you’re out getting frozen yogurt, this type of conversation will surely bring you closer together.
So, let’s check out some deep questions to ask your best friend and get you started on the road to discovery!
1. What does our friendship mean to you?
This is a great place to start. You can dive deeper into what your relationship means and what you want it to mean. Do you have fun together, do you share everything? Or are you practically family? [Read: How to build lasting friendships in life]
2. Are you afraid of dying?
Although it is likely something we all think about time and again, it is very possible you’ve never spoken to your best friend about it. Sharing your greatest fears may not make them dissipate, but it can help you get them off your chest.
3. What do you think happens when you die?
This is a controversial BFF question! Is there a heaven and hell? Do we just disappear? Are we still connected to our bodies? Do we become ghosts?
There is a lot to share here, and who better to discuss it with than your BFF? [Read: The unique traits that make a person trustworthy]
4. Do you want to have kids?
Another personal question that would be inappropriate for the lady down the street to ask, but from your best friend, it tells you about the future and can open up a whole new side to your best friend.
5. How is your relationship with your family?
Again, you may see your best friend daily, but talking about the ins and outs of family dynamics is not the easiest, especially if things are on the fritz.
Discuss where things are. Are they tense? Is there anything you can do to help? [Read: Family orientated – The meaning and what it means to be this person]
6. Are you really over your last breakup?
We all tend to put up a good front when we are in pain and reeling over a bad breakup. And although we stop talking about it before we stop thinking about it, it could still be very painful. Make sure your friend knows you are happy to let them vent.
This is one of the best deep questions to ask your best friend because it leads to healing.
7. What is your biggest regret?
Think about your biggest regret, wouldn’t talking to someone you love and trust about it make it a little less heavy to carry around? [Read: 50 nice things to say to your best friend to brighten their day]
8. Who do you idolize the most?
And why? The person you idolize says a lot about who you are and who you aspire to be. Ask this BFF question and find out!
9. What makes you furious?
Politics? People not recycling? Texting and driving? Your alarm clock? Your parents annoying you to get married and give them grandchildren? Who knows, you probably share a lot of the same pet peeves.
10. If you could go back to any time in your life, when would it be?
Would your best friend go back to high school? Would they want to change things or just experience them again? [Read: Why your blunt bestie is a big boon in disguise]
11. Are you satisfied with where your life is right now?
This can really open up a can of worms, but it is important to admit if you’re unhappy so you can do something about it. And if they are happy, celebrating that with the person you’re closest to means a lot.
12. When was the last time you cried? And why?
Did they cry recently because they fought with their partner? Did they cry when they saw a baby at the store?
13. Is there anything you would change about me?
Do not pose this deep question to ask your best friend if you are not prepared to hear the answer or answer it yourself.
But, if this person is really your best friend, they likely know a lot about you. That means they know your flaws, yet they still chose you as their best friend.
So, the answer couldn’t be too bad. [Read: 25 personal questions to ask your best friend and feel instantly closer]
14. Have you ever kept a secret from me? If so, why?
They most likely had a good reason for keeping something from you, or maybe they admit they were wrong and would have done something differently if they could.
Using this BFF question to discuss stuff you may have swept under the rug can make your relationship stronger. [Read: How to make your life better through friendship]
15. If you found out my partner cheated on me, would you tell me? And vice versa?
This is something you should definitely discuss with your best friend. Honesty is the best policy, but knowing your best friend’s take on the situation is very important.
If something were to happen, would they want to hear it from you or their partner? And would they feel comfortable telling you?
16. Do you believe in ghosts, psychics, etc.?
Many people are intrigued by mediums and ghost sightings, and this is always so fun to talk about. It isn’t just about scary stories but lets you into your friend’s beliefs.
Do they think their family members are watching over them? Do they think psychics are real? Or are they super skeptical about the whole thing? This BFF question will reveal the answers! [Read: Why online dating is more terrifying than a horror film]
17. Are you afraid of getting old?
So many people are afraid of aging. Whether it is the vanity, the health aspect, or just the fact that life is getting shorter, sharing this deep question with your best friend will guide you into the future together.
This isn’t one of the fun questions to ask your best friend, it’s a lot deeper in fact, but it’ll give you serious insights.
18. Is there anything you’re afraid you’ll never accomplish?
Afraid you’ll never meet someone? Maybe your friend fears never traveling the world or being completely fulfilled at work.
This question can lead to a pep talk from one another to make sure these fears are just fears and not realities. [Read: Best friend bucket list – 15 adventures for you and your BFF]
19. Do you believe in God?
No matter your religion or lack thereof, sharing your belief system with your best friend can clue you into things you may know about each other but never fully understood. [Read: How to be a good friend – The friend code all BFFs must follow]
20. Have you ever not told me when you were upset with me?
This can help air out old wounds. They could be holding onto something from a long time ago, and this gives your best friend a chance to get it off their chest.
This is a great deep question to ask your best friend because coming out of it your friendship will be stronger.
21. What is your most intense memory?
You’ll notice we mentioned the most intense memory, not the best for this BFF question. That is because your most intense memory, whether good or bad, impacts you a lot more than you’re happiest.
This lets you and your best friend really talk about your past and dive deep into the meanings of memories. [Read: Old love letters and memories – Should you keep them or throw them away?]
22. Who do you wish your relationship was different with?
Maybe they wish they were closer to their dad or grandparents. Or, perhaps, their romantic life isn’t what they want it to be.
Talking about this and opening up about it is a great way to get closer to your best friend through deep questions and help them with something they are struggling with.
23. How do you wish the world were different?
We bet there are tons of ways. They wish there was no more traffic, no more racism or sexism, and no more ridiculous robocalls.
You can bond over your answers to this deep question to ask your best friend. And, although these answers can be funny, they can get pretty serious. [Read: The big lessons you need to survive on your own]
24. Do you wish I was closer to the other people in your life?
Asking your best friend this deep BFF question shouldn’t come from a selfish place. It is nice to know if your best friend wants to share you with their family and other friends.
Do you hang out with just the two of you? Do they wish you were closer to their partner? Getting this answer can make your friendship even better. [Read: 19 ways to genuinely connect with others]
25. What movie from your childhood impacted you the most?
Was it a cartoon? Perhaps it was something they watched with a sibling or parent.
Discussing this can even lead to a fun and nostalgic movie marathon.
26. What is the best gift you ever received?
You may hope it was from you, but listen to what they say and their reasoning. This deep question to ask your best friend can really get them thinking.
Maybe they got the most expensive gift from their partner, but when their grandma gave them a locket with their photos in it, it meant the most. [Read: The little things in love that makes romance better]
27. Which family member do you think you’d be friends with if you weren’t family?
This is always a fun and deep question to ask your best friend. It is also a safe question to ask with someone you trust. It is no secret that we don’t like all our family members, even though we love them.
So, which would your best friend choose to spend time with, even if it was in their genes? [Read: How to see the signs of toxic family members and cut them loose]
28. What language or languages do you want to learn?
We personally find this BFF question so telling. And it isn’t just the answer, but the reasoning behind it. For example, does your best friend want to learn Italian so they can live there for a year? Or maybe they want to learn Spanish so they can communicate with their grandparents.
This is one of the fun questions to ask your best friend that could lead to travel opportunities!
29. If we could go anywhere in the world right now, where would you want to go?
Right this second. If you could just blink and be somewhere, where would your best friend want to go? Would they want to see the Eiffel Tower, or would they want to be home in bed, asleep? [Read: 15 reasons why you should travel at least once a year]
30. Is there anything you want to know about me?
We presume that your best friend would be asking a lot of these questions back to you, but there may be something else they want to know. And being an open book with your BFF, you should be able to answer anything that came at you with.
When it comes to fun questions to ask your best friend, they should always lead to a positive outcome.
31. 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]
32. What animal would you be if you could choose?
Bunny? Dog? Fish? It’s a silly BFF 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!
33. What’s your favorite holiday?
Everyone has a favorite. Christmas? Thanksgiving? Easter? You can only pick one!
34. 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? [Read: 8 small ways to deal with big changes in your life]
35. 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? This is definitely one of the fun questions to ask your best friend that’ll open your eyes!
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 can actually help you find out a lot about them!
36. Are you a dog or cat person?
There’s always one that we like over the other. Make them pick one with this BFF question, no matter how hard the decision is to make! [Read: Fur baby – Why millennials are choosing puppies over babies]
37. 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?
38. 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.
39. Would you rather go skydiving or cliff jumping?
Although this isn’t the most telling BFF 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 together. [Read: Best friend bucket list – 20 exciting adventures for you and your BFF]
40. 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.
41. 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.[Read: 50 hardest would you rather questions that have no right answers]
42. 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? As far as fun questions to ask your best friend go, this is a great one! [Read: The girl’s guide to strip clubs and female strippers]
43. 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.
44. 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.
45. 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]
46. 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.
47. 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! [Read: Unlucky in love? How to turn things around and get lucky instead]
48. What book changed you?
Have they read a book that really changed their outlook on life? Which book was it? Ask this BFF question to find out!
49. Is there a smell that makes you think of me?
Let’s just hope they don’t say dog poo or dirty socks! This BFF question might surprise you!
50. 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.
51. 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]
52. 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?
Some fun questions to ask your best friend will shock you, but hopefully, this one won’t be too much!
53. 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! [Read: 19 annoying and irritating boyfriend habits and traits you should avoid at all costs]
54. 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.
55. 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. [Read: Couples bucket list – 32 must-do things to create experiences together]
56. What is something you have always wanted to do but are afraid you’ll never be able to do?
This BFF 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]
57. Would we be friends if we met earlier?
What do you guys think? Would you? Ten years ago, you may have been a completely different person before you met them.
58. 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! Ask this BFF question and have a good giggle.
59. 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]
60. When was a time you were really disappointed in me?
It’s a hard BFF question to ask and even harder to hear the answer. But this can help you grow as a person and as friends.
61. 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.
62. 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. [Read: Self-concept – How we create and develop it to control our happiness]
63. 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.
64. Who is the most important person in your life?
This is such an important BFF question. Whether it is their mom, sibling, child, or even pet, this lets you know who you should maybe get to know better.
65. 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. [Read: How to get over your first love with a happy memory]
66. 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]
67. 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.
68. 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.
69. 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.
70. What do you think about soulmates?
Do they believe in soulmates? Are you two soulmates?
Fun questions to ask your best friend also reveal the depth of your friendship, and that’s never a bad thing. [Read: Twin flame – What it is, 41 signs & ways to recognize your twin soul]
71. 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]
72. 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.
73. Who last made you cry?
You’ll probably want to go smack that person in the face! Ask this BFF question and find out who it was.
74. 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. [Read: What is considered cheating? The painful types and ways to set boundaries]
75. 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.
76. 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 have this in common by asking this fun question to ask your best friend!
77. 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!]
78. 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. [Read: How to be fearless – 18 ways to set aside fear and live like a champion]
79. 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.
80. 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 if you ask this BFF question. [Read: Do you REALLY know them? 20 fun questions to ask a friend]
81. 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.
82. What is something no one knows about you?
This can be something like your friend keeps a journal, loves to paint, or put a child up for adoption. This can get really deep so be prepared.
83. 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]
84. 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.
85. 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? [Read: 5 ways volunteer work can help heal depression]
86. 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. Just remember that if you both have differing views, the conversation could become heated.
87. 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.
88. 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]
89. 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?
90. 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.
91. 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]
92. 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?
This fun question to ask your best friend could lead to some serious adventures!
93. Who was the first person you had a crush on?
Everyone remembers their first crush. Everyone. It’s like knowing your phone number – impossible to forget. This question is a fun way to take you and your friend down memory lane. [Read: How to make REAL friends outside your social networks]
94. What is your dream job?
This is one of the standard questions to ask a friend. Doctor? Actress? Teacher? What’s your friend’s dream job? What’s YOUR dream job?
And why aren’t you two working your dream jobs right now? Maybe with each other’s help, you can actually achieve your dream jobs. Unless it’s an astronaut, sure, it’s still possible – but a solid challenge. [Read: 17 bad friends that you should unfriend from your life]
95. What’s your biggest insecurity?
We all have our insecurities! Maybe your friend is insecure about her smile or the scar on her arm from falling off her bike. The list of insecurities that people have can turn into a scroll.
It’s important to know your friends’ insecurities because you’ll want to discover them – just in case you’ve been teasing them about it this whole time *and then stop*.
96. What do you love about yourself the most?
Ahh, it’s a beautiful thing when you see someone show you what they love about themselves because it’s probably what you love about them as well. That’s why this is one of the best fun questions to ask your best friend.
97. What have you always wanted to try?
This question is great for getting you both off the couch and crossing something off of your bucket list. River rafting? Bungee jumping? Whatever it is, you have to try it together. [Read: How to be good friends with a co-worker]
98. If you could live anywhere in the world for a year, where would it be?
This is one of our favorite questions to ask a friend. Because it often ends with Googling destinations and rental properties!
99. What would you eat for your last meal?
Is it pizza? Calamari? Pasta? Steak? Wait, there’s just too many options. Or maybe it would be a fruit salad. Who knows! But you can ask this BFF question and find out.
100. What would be your perfect day?
On the beach with a cute guy who rubs suntan lotion on your back? Playing video games with your best friends without your mother yelling at you? This fun question to ask your best friend could lead to the best day ever! [Read: Do you think alike? 20 questions to ask your best friend]
Which of these BFF questions will you start with?
Learning a few fun questions to ask your best friend, along with some deep ones, will help you get to know each other much better.
You might think you know everything there is to know, but the reality might surprise you!
[Read: The 8 types of friends everyone needs in their life]
Using this list of deep questions to ask your best friend can only further enhance your friendship and strengthen your bond. So, go on and ask, the answers will be telling.
