You may think you and your best friend know everything about each other, but there are still surprisingly plenty of questions to ask your best friend.
Find all the best questions to ask your best friend below and immediately start having better, more interesting conversations.
When looking for questions to ask your best friend, start with the best. These are the best questions out there to start a great conversation that can go anywhere with your friend, and wherever it goes, it’s interesting.
Here are 11 best questions to ask your best friend:
1. What is one thing you regret having done or not done in your life?
You and your friend probably rarely discuss regret; do so now.
2. What do you think has been the hands-down funniest moment in our friendship?
Relive the best moments.
3. Which famous person would you like to be BFFs with?
See the qualities your friend likes in you in their celebrity choice.
4. What are you best at?
Find out more about what your friend thinks about themselves.
5. Who do you wish you could get back into contact with?
Who is the long-lost friend that might enrich your friend’s life?
6. What’s a common experience for many people that you’ve never experienced?
What part of life are they missing out on?
7. What’s the most amazing true story you’ve heard?
A great chance to tell each other stories.
8. What’s something you were really stressed about, it turned out to be no big deal?
Helping with stress is a major best friend job, so what actually stresses your friend out?
9. Who or what is your nemesis?
Maybe a silly question to ask your best friend, but it may lead to a real answer.
10. What is the best compliment you’ve ever received?
Learn the sort of compliment that really builds your friend up.
11. What’s the best thing about your life right now?
Take a chance to take stock and appreciate things.
When you are looking for questions to ask your best friend, you’re probably also looking for a way to start a conversation that has such questions.
Use these conversation starters to get the conversation going.
Here are 9 conversation starter questions to ask your best friend:
12. Have you considered running for president?
You’d be surprised how many people say “yes.”
13. If you could buy one material thing, and money was not an issue, what would it be?
What does your friend really want?
14. What movie can you watch over and over without ever getting tired of?
Ask, then watch it together.
15. In the past people were buried with the items they would need in the afterlife, what would you want buried with you so you could use it in the afterlife?
Probably their iPhone, but ask to be sure!
16. What’s your favorite hobby to do alone?
A great way to start talking about how you behave without each other around.
17. What’s your biggest pet peeve?
If there was ever a question to ask your best friend to get a conversation started…
18. Where’s one place you’d like to go that you haven’t been?
Find out and make a plan to go together soon.
19. What is something that is popular now that annoys you?
Another chance to grumble about the world and have a great conversation.
20. What was your best birthday?
Find out, make notes, and top it next year.
The point of a question is, after all, to get to know something. So, you want the questions to ask your best friend to also be get to know you questions.
Use these to really get to know them.
Here are 8 get to know you questions to ask your best friend:
21. If you had to choose one thing you were most passionate about, what would it be and why?
Get straight to the point about what your friend cares about.
22. What music do you listen to to lift your spirits when you’re feeling down?
Music says a lot about a person.
23. What is the most important material possession you have and why?
The choice will explain how they relate to the world.
24. What is the most important memory you have and why?
That memory helped make the person.
25. What are you currently worried about?
Politics, exams, romantic partners: find out what’s really on their mind.
26. What are some of your own personal goals in the next 5 years?
Where does your friend see themselves in the future?
27. What’s one thing you want to do before you die?
Get a peek at the bucket list.
28. What’s the scariest thing you’ve ever done?
Find out what scares them, and how they overcame the fear.
When you’re looking at questions to ask your best friend, sometimes the best questions and answers come from random questions.
Random questions get more genuine answers because they come out of nowhere. Use the questions below to get some unexpected and honest answers.
Here are 9 random questions to ask your best friend:
29. How old is the most expired item in your fridge?
What does your friend think they like to eat but don’t actually like to eat?
30. What’s under your bed?
You may or may not want to know the answer.
31. 100 kittens or 3 baby sloths?
It’s almost too much cute either way.
32. What’s the most expensive thing you’ve broken?
Find out if you should trust them with your precious objects.
33. What invention doesn’t get a lot of love, but has greatly improved the world?
Nail clippers? The cushioning in shoes? Be grateful for the little stuff.
34. What’s your favorite beer?
Get a recommendation and a great conversation about beer.
35. What is the most interesting piece of trivia you know?
A sure way to get a great fact.
36. Bruce Willis or Harrison Ford?
Who is the ultimate charming action movie hero?
37. Would you rather have one real get out of jail free card or a key that opens any door?
The follow up questions are almost as interesting as the original.
Having funny questions to ask answers a basic question problem: how do you find questions to ask your best friend that your best friend will respond to?
If you get them laughing, they’ll be game to answer anything. Use these questions for a chuckle and a good answer.
Here are 8 funny questions to ask your best friend:
38. Would you rather wear a snow suit in the desert or be naked in Antarctica?
Choose your discomfort.
39. If you could switch two movie characters, what switch would lead to the most inappropriate movies?
Work through the story implication for more hilarity.
40. What’s the most epic way you’ve seen someone quit or be fired?
Dreaming about the epic-ness is great therapy after a bad work day.
41. What was cool when you were young but isn’t cool now?
Enjoy some nostalgia and the end of your coolness.
42. Would you rather have hands that kept growing as you got older or feet that kept growing as you got older?
Think of all you could grab with those massive hands.
43. Would you rather give up bathing for a month or give up the internet for a month?
You’d have one stinky friend.
44. What would you NOT do for 5 million dollars?
Come up with ridiculous scenarios and see if your friend takes the money.
45. What’s closest you’ve ever come to being arrested?
It’s definitely going to be a good story, no matter what.
A great font of questions to ask your best friend can come out of never have I ever questions. If you and your friend play, you’ll find out loads about them while also having a great time.
Try a few of these for some playful and insightful responses.
Here are 8 never have I ever questions to ask your best friend:
46. Never have I ever bragged about something I have not done.
Get them to expose the lie and find out why.
47. Never have I ever Lied to a friend to avoid a greater evil.
Find out the greater evil along with the lie.
48. Never have I ever Fallen asleep in the cinema.
What movie was so boring to deserver it?
49. Never have I ever watched the “Gangnam Style” music video and tried to do the dance.
Get them to do their best Gangnam.
50. Never have I ever faked being sick so I could play video games.
Just how passionate is your friend for gaming?
51. Never have I ever Googled my own name to see what comes up.
This is one of the best questions to ask your best friend to find out how vain they are.
52. Never have I ever pretended I was running from zombies while on a run.
It’ll help get you that extra mile.
53. Never have I ever been scared of the dark.
Sure they have, but how recently?
Truth or Dare questions can get people laughing, having a good time, and revealing secrets about themselves.
Use these questions and dares to find out what your friend doesn’t want to reveal about themselves.
Here are 8 truth or dare questions to ask your best friend:
54. If you were a giant, what would you like to do?
Make a stack of cash in the NBA, obviously.
55. Go outside, and while skipping down the street, sing “Let it Go” from Frozen.
You know they always wanted to do it anyway.
56. Go in the kitchen and rearrange everything in the food pantry in alphabetical order.
They’ll wish they took the truth after this one.
57. How long have you gone without showering?
Are they ultra- or anti- hygienic?
58. What’s the dumbest thing you’ve ever done on a dare?
Find out just how far they’ll go in this game.
59. How many best friends have you had during your lifetime?
How big is the group you include yourself in now?
60. What is the craziest thing that you have ever done while drunk?
Get a great story and make sure you’re involved in the next version they tell.
61. Drink chocolate syrup straight out of the bottle.
You’ll only have to ask once.
When the topic of questions to ask your best friend comes up, probably what you really want are deep questions to ask them.
Deep questions open up areas that friends often purposefully avoid, but that they really want to discuss together anyway. These questions give you the opportunity to open those conversations up.
Here are 9 deep questions to ask your best friend:
62. Where do you think is the most worthwhile place to find meaning in life?
What is the place that can provide the most and best answers for life? Go there together.
63. Do you believe in faith and superstition?
For some, the most important deep question of all.
64. What social stigma does society need to get over?
Everyone thinks society is too prudish in one way or another.
65. What Is the Most Important Aspect of One’s Personality That Is Not Associated with a Person’s Appearance?
Find out what part of a person’s character really matters to your friend.
66. What is one dream you have yet to accomplish?
Find out and help them achieve it.
67. Who is your greatest hero?
A real hero has a profound effect on how a person lives their life.
68. Have you ever made a decision that changed your entire life? If so, what was it?
Get the story of how your friend got to the place they’ve arrived today.
69. What’s one thing that defines who you are?
How we define ourselves is a large part of how we present ourselves to the world.
70. What’s one thing that bothers you most about the world today?
They can only choose one, so it’ll be big.
Downloadable List of Questions To Ask Your Best Friend
Here is a downloadable list of questions to ask your best friend (right click the image and select Save Image As…):
More Best Questions to Ask
Need more questions for friends or for others? Mantelligence has it covered, just try these:
- Get all the best questions to ask a girl right here.
- Show you’re interesting by asking all the right interesting questions.
- Chat with any guy, friend or not, with these questions to ask a guy.
Using questions for your best friend is easy enough. All you have to do is follow these three steps:
Here are 3 of steps on how to ask questions to ask your best friend:
1. Choose the right moment
Find a moment when you and your best friend have time for a good chat and are in the mood to give real answers.
2. Choose the right type of question
Not every question is right for every moment. Go silly or serious depending on the mood.
3. Let them answer and move the conversation their direction
Let them give a full and thought-out answer, then let them choose how the conversation progresses.
With the above questions to ask your best friend, you have great lists of questions to ask that lead to all manner of serious and silly conversations, all of which reveal new truths about your friend.
You now have questions to ask friends that can keep any conversation interesting, no matter the context. Get out there and learn more, have more fun, and enrich your friendship.