80+ Hard Questions To Ask Your Friends

hard questions to ask your friends

Here are 81 extremely hard questions to ask your friends to get to know them better. There will come a time in your life when you will want to have a true friend, with that being said, they are really hard to come by. The trick is to get to know your friends inside out before deciding if you want to keep them around for life. 

Make sure that you tread carefully when asking your friends the following questions, some may actually get offended. You also want to choose your timing carefully before asking some of these questions. The aim is to get to know your friends, not scare them away.

hard questions to ask your friends

Hard Questions To Ask Your Friends

Questions are meant to use as conversation starters but sometimes, you may want to get to know your friends a lot better. This is where hard questions come in. To understand a person, you will need to know their fears, inner thoughts, and secrets. use the following questions to help you determine if you’ve found the perfect friend.

#1 Do you trust me?

#2 Do you think I would ever disappoint you?

#3 Does our friendship qualify as true friendship?

#4 What do you hate about me the most?

#5 Do you think that honesty makes friendships stronger?

#6 Do you judge me when something goes wrong or do you think of ways to help?

#7 What are your favorite memories about us?

#8 Who was your favorite childhood friend?

#9 Do you believe in God?

#10 Do you believe that everyone has a soulmate?

#11 How long did it take you to trust me?

#12 If you had to move away, would you remain friends with me?

#13 Do you believe in life after death?

#14 If your partner told you to quit being friends with me, would you?

#15 What are some tough lessons you had to learn the hard way?

#16 If you had to choose 3 things to make your life more bearable, what would they be and why?

#17 When was the best time of your life?

#18 When was the worst time of your life?

#19 What are friendship dealbreakers for you?

#20 What do you want people to remember about you the most after you are gone?

#21 What would be life-changing for you?

Extra Hard Questions To Ask 

#22 If you had a problem, who is the one person you would run to first?

#23 Have you ever lost someone very close to you?

#24 When you are in a bad mood, would you prefer to be left alone or comforted?

#25 Do you believe that people should be given second chances?

#26 Do you feel misunderstood at times?

#27 Would you prefer to be confronted about a situation?

#28 What do you have on your bucket list?

#29 What is something you’ve done that you would do all over again?

#30 If you could do anything in this world without consequences, what would it be?

#31 When you define the word bravery, do you think of yourself as a brave person?

#32 When you look at me as a person, what comes to your mind right away?

#33 Do you feel like you are unstoppable?

#34 What are some of the emotions you experience most in your life?

#35 Do you think you are likable?

#36 What are some of your best traits as a person?

#37 Are you envious of other people?

#38 What drives you the most to become a better person?

#39 Are you competitive?

#40 How do you think you make people feel when they are around you?

#41 Do you think that lying to a friend is acceptable?

#42 What are your vulnerabilities?

#43 What do you like most about yourself?

#44 Do you think that I am a good friend?

#45 Where do you see our friendship in 10 years?

#46 Do you regret knowing me?

#47 If you could change anything about me, what would it be?

#48 If you could change anything about yourself, what would it be?

#49 What makes you feel loved?

#50 What will hurt you the most in a friendship?

Deep Questions To Ask Your Friends

#51 What is something that happened in your life that you just can’t seem to forget?

#52 Who hurt you the most in your life?

#53 What is a secret dream you have that no one knows about?

#54 How do you define the word friendship?

#55 Do you think that what we have is considered a real friendship?

#56 If you had to choose all over again, would you choose me?

#57 What makes you feel angry the most?

#58 What actions make you feel irritated?

#59 What are your utmost fears?

#60 Do you prefer friends with riches?

#61 How do you picture your future?

#62 Do you believe in status and success?

#63 What experiences made you see the world differently?

#64 Do you want to get married?

#65 How many children you do plan on having?

#66 What are things about you that I don’t know about?

#67 Would you marry someone from another religion?

#68 Which would you listen to, your head or your heart?

#69 If you could make one wish, what would it be?

#70 What inspires you the most?

#71 Who is your inspiration?

#72 Who would you call if you were ever in trouble?

#73 If you could change important dates in your past, what would they be and why?

#74 What makes you feel grateful?

#75 Who would you put first, family or friend?

#76 What did you learn from failed relationships or friendships?

#77 What is the best advice you’ve ever been given and by whom?

#78 What do you think about regularly when you are alone?

#79 What qualities do you want your life partner to poses?

#80 What do you think would make our friendship stronger?

#81 Do you think our friendship can survive any obstacle?

Can You Ask New Friends These Questions?

yes! Absolutely! It’s actually better to ask new friends hard questions because it helps you decide if you should or shouldn’t pursue the relationship, to begin with. Just a word of caution, let the question be mutual, and don’t let them come out as an interrogation.


There you have it! 81 hard questions to ask your friends to get to know them better. If you liked this post, please share it with your friends. I would also love to hear your thoughts in the comments below. Until next time, please have some fun!

psyco facts

We share researched psychological facts on life, love, relationships, and everyday happenings!

Recommended Articles

Leave a Reply

Your email address will not be published. Required fields are marked *