You may think that you know everything there is to know about your best friend, but if that’s how you feel, it’s only because you’re not asking them the right questions.
Asking your best friend questions is the best way to get to know them better, connect in a more meaningful way, and strengthen your bond with them.
If you need some help knowing exactly what to ask in order to spark deeper conversation, or even just want to enjoy some funny, lighthearted conversation with your bestie, then you came to the right place.
Start having more interesting conversations with your BFF with the following 173 questions.
Sections
- Funny questions to ask your best friend
- Deep questions to ask your best friend
- Questions to ask your best friend about yourself
- Funny questions to ask your best friend about yourself
- Questions to ask your best friend of the opposite gender
- Weird questions to ask your best friend
- Personal questions to ask your best friend
- Random questions to ask your best friend
- What questions should you avoid asking your best friend?
Funny questions to ask your best friend
There are very few better ways to spend your time than hanging out with your best friend. There is no one that understands you better and that you can laugh harder with. Just in case you need some inspiration to help you laugh harder than ever with the person that you love, here are 27 fun questions to ask your BFF when you’re bored.
1. If there were no consequences for a day, what would you do?
 
2. What would you name your alter ego?
 
3. Which word best describes our relationship?
4. If you could stay one age forever, which would you choose?
 
5. Which of us do you think is more likely to get arrested?
 
6. If you won the lottery, what’s the first thing you would buy?
7. If you were a flavor, what would you be?
 
8. What’s the first thing you do when you’re bored?
 
9. Would you ever go to a strip club with me?
10. If you could choose any celebrity to be best friends with, who would you choose?
 
11. Do you wish that you could delete all your social media and just go off-grid?
 
12. I’m your best friend, right?
13. What is the worst first date you’ve ever been on?
 
14. Do you think I would make a good best man or maid of honor?
 
15. If you could choose one thing about me to change forever, what would it be?
16. Do you have any recurring dreams or nightmares?
 
17. What is the most embarrassing moment of your life?
 
18. Do you do anything weird when you’re home alone?
19. How do you think your ex would describe you?
 
20. What’s the most toxic quality that you are attracted to in the opposite sex?
 
21. Would you get a matching tattoo with me? If so, what would you want?
22. Where’s the most embarrassing place you’ve had to pee?
 
23. Would you let me look through your browser history?
 
24. What confuses you most about the opposite sex?
25. What movie has completely scarred you for life?
 
26. What would the sitcom of our friendship be called?
 
27. What did you want to be when you grew up?
You might be interested in this list of fun questions to ask your friends.
Deep questions to ask your best friend
It might seem like you know all there is to know about your best friend, but there is always more to learn. You just need to ask the right questions. Here are 25 thoughtful and deep questions to ask your best friend to get to know them better.
1. Do you feel genuinely happy about your life?
 
2. Is there anything about your life that you wish you could change?
 
3. What’s the happiest memory you have from your childhood?
4. When you can’t sleep, what are you thinking about?
 
5. Do you feel like I support you well through the hard times of your life?
 
6. What’s the happiest memory you have of us together?
7. Do you ever worry that you won’t end up finding someone to spend your life with?
 
8. What’s one thing about yourself you wish you could change?
 
9. What in your life do you feel the most proud of?
10. Who is the last person that made you cry, and why?
 
11. What motivates you to get out of bed in the morning?
 
12. What is the biggest challenge you’re facing in your life right now?
13. On a scale from 1-10, how much do you think your childhood still affects you today?
 
14. Is there anyone in your life that you wish you were closer with?
 
15. Have you ever wanted to die?
16. What’s the hardest goodbye you’ve had to say?
 
17. What’s one thing about yourself that you absolutely love?
 
18. What do you think is the meaning of life?
19. What do you think is your greatest strength?
 
20. What’s the best compliment you’ve ever received?
 
21. What’s the worst decision you’ve ever made?
22. What’s one thing I could do that you’d consider unforgivable?
 
23. What’s the most loved you’ve ever felt?
 
24. Who was your first friend? Are you still friends with them?
25. What’s a day that you wish you could forget forever?
Go here for a list with more deep questions to ask your friends and get to know them better.
Questions to ask your best friend about yourself
Have you ever wondered what your best thinks about you and just how well they know you? These questions to ask your best friend about yourself are a little on the serious side, but they will help you see how well your BFF knows you.
1. What do you really think about me?
 
2. If I could spend every day for the rest of my life doing one thing, what do you think I’d choose?
 
3. Do you think I’m happier right now than I was a year ago?
4. Has the way you see me changed over the course of our relationship?
 
5. How do you think I would describe you?
 
6. What’s the most impressive thing I’ve done since we’ve known each other?
7. What is my biggest fear?
 
8. What’s one thing about me that only you know?
 
9. What do you think is my biggest weakness?
10. What do you think is my biggest strength?
 
11. What was your first impression of me?
 
12. How do you describe me to your other friends?
13. What physical feature am I most insecure about?
 
14. Why do you think we get along so well?
 
15. Am I more of a cat or a dog person?
16. Who in my life has hurt me the most?
 
17. How would you describe me in one word?
 
18. What’s one thing I never leave the house without?
19. Where can you usually find me?
Funny questions to ask your best friend about yourself
If you want to have fun testing your best friend to see just how well they know you, then these are the perfect questions for you. Enjoy laughing with your BFF while learning exactly how they see you and your relationship together.
1. Which game or reality TV show would I enjoy being on the most?
 
2. Which of my exes do you think I’d be most likely to get back together with?
 
3. If I called you to bail me out of jail, what would you assume I got arrested for?
4. If I won the lottery, what do you think I would buy first?
 
5. What job would I be perfect for?
 
6. If I was famous, what do you think it would be for?
7. What is my biggest pet peeve?
 
8. What would I choose as my last meal?
 
9. How would I spend my perfect day?
10. What’s one life lesson you wish I would just learn already?
 
11. When we met, did you think we would become best friends?
 
12. If I was an animal, what would I be?
13. What do you consider my most embarrassing moment in our friendship?
Questions to ask your best friend of the opposite gender
If you have a best friend that is of the opposite gender, then you have the perfect opportunity to get to know things about the opposite sex that you otherwise wouldn’t be able to. These are the best questions to use to ask your best friend to get to know them better and maybe gain some insight into the ways of the opposite gender.
1. How would you spend a day as the opposite sex?
 
2. What is the weirdest thing about being your gender?
 
3. Do you think it’s possible for girls and guys to just be friends?
4. Do you think that I’m open-minded?
 
5. What advice do you have for my dating life?
 
6. Do you think we would make good co-parents?
7. Has being friends with me taught you how to be a better partner to your next girlfriend or boyfriend?
 
8. What is the most attractive quality about me?
 
9. Do you think we would make a good couple?
10. What is one thing about the opposite sex that you really admire?
 
11. What is one thing about being a boy or girl that you’ve always wondered about?
 
12. What is your favorite part of our friendship?
13. What area of my life do you think could use the most improvement?
Questions to ask your guy best friend
Compared to women, men often struggle to maintain their friendships.[1] Men sometimes struggle to connect deeply with their friends and can feel nervous to talk about more personal topics. If you are looking for thoughtful questions to ask your guy best friend to get to know him better and help him open up, then these are good questions to do so.
1. Who is the biggest role model in your life?
 
2. What was your best mic drop moment?
 
3. What quality of yours do you consider to be your best?
4. Is there anyone in your life that has completely lost your respect?
 
5. When was the last time you cried?
 
6. What is one thing you could talk about all day if given the chance?
7. What qualities does your perfect partner have?
 
8. What movie do you wish was more like real life?
 
9. How many phones have you either lost or broken?
10. What three events had the biggest impact on who you are today?
 
11. Would you rather hang out with the boys or your significant other?
 
12. What is the most useless skill you have?
13. Do you find it easy to ask others for support or feel like you have to do everything on your own?
 
14. What is one skill that you wish you had?
 
15. Is there anything you would never do for a million dollars?
16. Do you feel comfortable crying in front of other people?
 
17. Do you believe relationships should be 50/50?
 
18. Was your dad an inspiring person in your life for you?
19. What celebrity would make the worst president?
 
20. Would you rather spend an afternoon playing a sport or watching a game?
Questions to ask your girl best friend
Tired of talking to your BFF about their crush? These are good questions to ask your best friend if you want to connect on a more personal level with her and also have the potential for some good laughs as well.
1. What in your life do you still really want to accomplish?
 
2. Where do you hope to be one year from now?
 
3. Do you wish you had better support in your life?
4. When you think about me, what’s the first thing that comes to mind?
 
5. Is there anyone you’re missing right now?
 
6. What’s the best thing about your life right now?
7. What family member do you feel the closest to?
 
8. Would you ever have a sugar daddy?
 
9. What would your dream job be?
10. What hair color do you think you would look amazing with?
 
11. Are you happy with the relationship you have with your family?
 
12. If you could go on a date with any celebrity, who would you choose?
13. What qualities do you look for in a partner?
 
14. What is something in your life you are working to change right now?
 
15. Do you believe there are good men left in the world?
16. What’s one thing you would never mention on a first date?
 
17. If you got a pet tomorrow, what kind of pet would you want, and what would you name it?
 
18. What’s your favorite thing to do when you’re by yourself?
Weird questions to ask your best friend
Here are some weird, but interesting questions to ask your best friend that are sure to shake up the conversation. Enjoy asking these 15 weird questions, and be ready for some surprising answers.
1. If your pet could talk, what do you think they would say about you?
 
2. Is there anything that you believe even though you know it’s probably wrong?
 
3. What was the weirdest habit you had as a child?
4. If your life was a video game, what cheat codes would you want?
 
5. Have you ever eaten a bug?
 
6. Have you ever screamed at the top of your lungs?
7. How many times in a day do you change your outfit?
 
8. Do you think blind people can see in their dreams?
 
9. How many times in a day do you think you lie?
10. Weirdest thing anyone has ever said to you?
 
11. If you had to give up brushing your teeth or your hair forever, which would you choose?
 
12. Who’s idea was it to milk a cow for the first time?
13. Would you rather have no arms or no legs?
 
14. If someone offered to give you the power to read minds, would you want it?
 
15. What’s the worst purchase you’ve ever made?
Here are more hilarious questions to ask your friends.
Personal questions to ask your best friend
Do you think you know everything there is to know about your BFF? Regardless of how long you’ve been besties, there is always more that you can learn about them. These are hard questions to answer, but the answers will help you to better understand your best friend and allow you to connect on a deeper level.
1. What was your childhood like?
 
2. What is one thing you’ve always wanted to do but are afraid you’ll never be able to do?
 
3. Do you feel worthy of love?
4. What is the one thing you think is holding you back?
 
5. Is there anything about yourself that you feel ashamed of?
 
6. Do you have any regrets?
7. If you had to pick someone in your life to have a kid with, who would you choose?
 
8. How much do you care about what other people think?
 
9. Who is the most important person in your life?
Random questions to ask your best friend
Tired of having serious conversations with your best friend? These are good questions to ask to spice up your conversation and keep your bestie on their toes.
1. What inanimate object would you marry?
 
2. If you were being robbed at gunpoint, what would you say?
 
3. What is the worst thing someone could put on their dating profile?
4. What mythical creature do you think is real?
 
5. How would you describe your romantic life in one word?
 
6. If there was a pole at a club, would you try and dance on it?
7. If you started a blog, what would you call it?
 
8. What’s the weirdest thing you’ve ever posted on the internet?
 
9. Do you think an elephant would make a good pet?
10. Which Harry Potter house would you want to be a part of?
 
11. Do you have any secret talents I don’t know about?
 
12. Did you ever do someone’s homework for them when you were younger?
13. What’s the largest purchase you’ve made that you paid for in $1 bills?
 
14. Have you ever been in a fight?
What questions should you avoid asking your best friend?
When it comes to figuring out which questions are appropriate for your relationship, there is no one-size-fits-all. Which questions are suitable to ask your best friend will vary depending on how close you are and also how comfortable they are answering deep questions about themselves.
Some people are closed books, and someone’s boundaries around what they feel comfortable sharing with you should always be respected. Respecting someone’s boundaries around what they are comfortable sharing is an important piece in building trust in a relationship. Give people the space to open up to you as they feel ready.
If you want to test the waters and begin asking more personal questions to a best friend, pay attention to how they react when you ask them. If they answer quite openly and comfortably, then it should be a non-issue.
Regardless, asking if they are comfortable sharing about that topic is always never a bad idea. If you notice your friend is obviously uncomfortable—meaning they avoid eye contact, they wince, or they move away—when you ask certain questions, honor the friendship and their need for privacy and refrain.
Here is a list of conversation topics that are generally best to avoid:
1. How many people they’ve slept with: Sexuality is a personal topic for a lot of people and should be treated delicately.
2. A traumatic experience: When it comes to difficult experiences, you should avoid bringing it up first. Allow them to start the conversation.
3. Questions about their body or weight: Avoid bringing attention to parts of someone’s body that they might feel self-conscious about, like scars or their weight.
4. Pregnancy: Don’t ask your best friend if they are pregnant. If they want you to know, they’ll tell you.
me and MY pookie had a lot of fun
me and pookie had fun
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me and pookie had fun 😀
It’s either me or my annoying best friend that has asked almost all the do not ask your best friend questions.