100 Questions to Ask Your Best Friend
These questions are for best friends who think they already know everything about each other. Start with the funny ones, pick a few from each group, and save the deep ones for a late night chat or a long trip. Ask them face to face, over text, or turn them into a quiz and see who really knows who.
Funny questions to ask your best friend
- If I got arrested, what would you assume I did first?
- We are stuck in a lift for three hours. Who panics first?Example: you / me / we both laugh it off
- What is the most embarrassing thing I have done in front of you?
- If I had a warning label, what would it say?
- I send you a voice note. How long is it, honestly?Example: 30 seconds / 2 minutes / a full podcast
- Which of my habits would make a terrible roommate run away?
- What is the weirdest thing you have seen me eat?
- If we swapped phones for a day, what would you be most scared I would find?
- You see me trip in public. What do you do first?Example: help me up / take a photo / laugh, then help
- What song would play every time I walk into a room?
- Which cartoon character am I most like when I am hungry?
- If I started a YouTube channel, what would it be about and how fast would it fail?
- I order food. How long do I take to decide?Example: 1 minute / 10 minutes / I let you pick
- What is the dumbest argument we have ever had?
- What is my most dramatic overreaction you still remember?
Funny questions to ask friends: would you ever
- Would you ever shave your head if I lost a bet?
- Would you ever go on a blind date I set up for you?Example: yes / only if you come too / never
- Would you ever post your worst photo of me if I paid you?
- Would you ever sing on stage with me, even badly?
- Would you ever eat something gross for a free meal?
- Would you ever go a week without your phone for me?Example: easily / maybe two days / not a chance
- Would you ever pretend to be my partner to get me out of an awkward date?
- Would you ever get a matching tattoo with me?
- Would you ever travel somewhere with me with no plan at all?
- Would you ever read my old diary out loud at my wedding?
- Would you ever let me pick your outfit for a whole week?Example: sure / one day only / no way
- Would you ever take the blame for something I broke?Example: yes / only if it was cheap / no, you are on your own
- Would you ever wake up at 5 AM just to watch a sunrise with me?
- Would you ever tell my crush I like them if I asked?
Memories together
- What is the first thing you remember about me?
- When did you know we would be close friends?Example: day one / after a fight / slowly, over time
- What is our best inside joke, and how did it start?
- Which trip or outing with me do you still talk about?
- What is the hardest we have ever laughed together?
- What is one fight we had that you are glad we got past?
- Which day with me would you live again?Example: a trip / a birthday / a random boring day
- What is a photo of us you would save if your phone broke?
- When did I surprise you the most?
- What is the worst plan we ever made that still turned out fun?
- What is something I said once that you never forgot?
- Which time did I show up for you when you did not expect it?
- What is the silliest thing we got in trouble for?
- Which version of me do you miss the most?Example: school me / first-job me / the me from last summer
Think your best friend would get these right? Test them.
How well do you know me
- I have a free Sunday. What am I doing?Example: sleeping late / out with friends / watching shows all day
- What do I do when I am stressed but do not want to talk about it?
- What is the one food I would never share, even with you?
- I am in a bad mood. What fixes it fastest?Example: food / a nap / being left alone
- Which of my friends would I call first if I was in trouble?
- What do I always say when I am lying?
- What is my go-to order at our usual place?
- How do I reply when I am annoyed with you?Example: "ok." / no reply / a long paragraph
- What is the one thing I always forget?
- Which movie or show can I watch again and again?
- What is my biggest pet peeve?
- I get a surprise gift. How do I react?Example: overexcited / awkward thank you / I cry a little
- What am I secretly really good at?
- What would I do with a sudden extra month of holiday?
- Who do I pretend not to like but secretly do?
- What time do I actually fall asleep?
Loyalty and trust
- I text you at 3 AM saying I need you. What do you do?Example: call right away / come over / reply in the morning
- Someone talks badly about me when I am not there. What do you say?
- Would you tell me if my partner was not good for me?
- I tell you a big secret. Who would you be most tempted to tell?Example: no one / your mom / your partner
- Have you ever kept a secret for me that was hard to keep?Example: yes, many / just one / I am still keeping it
- If we liked the same person, what would you do?
- Would you lend me money with no questions asked?
- I make a terrible decision. Do you stop me or support me?Example: stop you / support you / both, loudly
- What is one thing I could do that you would never forgive?
- Would you tell me the truth even if it would hurt me?
- If I moved to another country, how would you keep us close?
- Have you ever defended me when I did not know about it?
- What makes you trust someone, and did I pass that test?
- I forget your birthday. How long do you stay mad?
Deep questions to ask your best friend
- What is something you have never told anyone, not even me?
- What are you most afraid of right now?
- What do you think I need to hear more often?Example: you are doing fine / slow down / you are loved
- When did you feel most alone, and did I know about it?
- What is one thing about yourself you are trying to change?
- What do you wish people understood about you?
- Is there a moment in our friendship you wish you could redo?
- What do you think is my biggest strength that I do not see?
- What helps you most on a bad day?Example: talking / quiet time / a distraction
- Who has had the biggest impact on the person you are today?
- What is a belief you used to hold that you have dropped?
- What does a good friend mean to you now compared to when we met?
- When was the last time you cried, and why?
- If our friendship ended tomorrow, what would you regret not saying?Example: thank you / sorry / I love you
Future plans and dreams
- Where do you see us as friends ten years from now?
- What is the first trip we should take together?Example: mountains / a beach / a city abroad
- Who will get married first, you or me?
- What would you name a business we start together?
- What do you want to achieve before you turn 40?
- When we are old, what will we still be fighting about?Example: food / who was right / directions
- Would you want to live in the same city as me forever?
- What role would you play at my wedding?
- What is one dream you have not said out loud yet?
- If you could change careers tomorrow, what would you do?
- What tradition should we start this year?
- What do you hope I never stop doing?
- We both win a big prize. What do we spend it on first?Example: a trip / a house / a party for everyone
Questions in our quiz
Our quiz has its own set of questions with ready answers to pick from. See the quiz questions.
More lists: Would you rather questions, Questions to ask your boyfriend, Questions to ask your girlfriend.
Common Questions
How many questions should I ask my best friend at once?
Five to ten is enough for one chat. Mix a few funny ones with one or two deeper ones so it does not feel like an interview. You can come back to the list any time.
Which questions are best to start with?
Start with the funny questions or the memories group. They get you both laughing and talking. Save the deep and loyalty questions for when you have time and some privacy.
Can I ask these questions over text?
Yes. Send one question at a time and wait for the answer before the next one. Voice notes work well for the longer memory and deep questions.
What are good funny questions to ask friends in a group?
The funny and "would you ever" groups work best in a group, because everyone can answer and argue. Ask one person, then let the others guess their answer before they reply.
How do I turn these questions into a quiz?
Make a free quiz on this site with no account: answer 20 questions about yourself, then share the link with your best friend. They guess your answers, and their score shows on your leaderboard next to your other friends.
Turn your favorite questions into a quiz and send it to your best friend.