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25 Personal Questions to Ask Your Best Friend & Bond like a Real BFF

You may see your BFF every day, but do you actually know them as well as you think? Here are the best personal questions to ask your best friend.

personal questions to ask your best friend

Sometimes even when we spend a lot of time together we don’t know the deeper side of our very best friend. There are tons of things you probably want to know about them and vice versa. So whether you are hanging out late at night or sick of scrolling through social media while lounging on the sofa, here are some personal questions to ask your best friend. [Read: How to create lasting memories with your best friend]

The best personal questions to ask your best friend

Best friends can be a lot of things. They can be someone you see everyday. They can be someone you have the most fun with, someone you go shopping with, someone you vent to.

#1 What was your childhood like? Someone’s childhood may seem like long forgotten memories, 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 8 types of friends everyone needs in their life]

#2 What scares you the most? 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.

#3 What is your first memory? Some of us remember things back to toddler years, others not until elementary school 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: Would you rather questions to leave you thinking]

#4 How would you describe me to a stranger? This is personal in the sense that you get to see how your friend views you. And be aware they will probably ask the same thing back. 

#5 Do you have high self esteem? We all struggle with insecurities now and then. And to know that you and your best friend share those struggles can feel relatable and bring you even closer. Not to mention you can lift each other’s spirits when those struggles get you down. 

#6 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?

#7 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.

#8 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 towards dating in the future, so learning this can help you give them advice too.

#9 What is something you have always wanted to do, but are afraid you’ll never be able to do? Personally this 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 hard.

But opening up to a friend like this can help release a lot of pressure you put on yourself.

#10 What is the biggest lie you ever told? This is not something you ask to hold something against your best friend, but learn why they told that lie. Were they a dumb kid at the time? Were they protecting someone? Or were they protecting themselves? [Read: The hardest would you rather questions to get to know someone better]

#11 What do you feel the most guilty about? Similarly to the last one, 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.

#12 Are you afraid of dying? You might think, DUH! Who isn’t? But depending on someone’s spiritual or religious beliefs the answer can drastically waiver.

#13 What is something no one knows about you? This can be something like your friend keeps a journal, they love to paint, or they put a child up for adoption. This can get really deep so be prepared.

#14 Are you close with your parents? Someone’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.

#15 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. 

Relationships with grandparents are something that I believe are so overlooked. So asking your friends about them can open that relationship to more possibilities.

#16 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.

#17 Have you ever cheated on someone? There is a lot to say for someone that has cheated on their partner. And as much as my own 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: The 15 qualities of a good friend that sets them apart]

#18 Do you regret anything? 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.

#19 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.

#20 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.

#21 Do you believe in God? 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.

#22 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?

#23 Do you want to have kids? Wanting to have kids is a huge decision. And it is no one’s right to try to change your mind one way or the other. But sharing your opinions and reasoning can be useful for you both. Not only can it bond you, but it can open your eyes to another point of view.

#24 How much do you care about what other people think? To some extent, everyone cares what others think. But how much lets you know how much your friend ignores and how much really affects their attitude and outlook. [Read: Do you really know your friend? Try asking these questions to see]

#25 Who is the most important person in your life? This is such an important question. Whether it is your friend’s mom, sibling, child, or even pet this lets you know who you should maybe get to know better.

[Read: How to be a good friend – The friend code all BFFs must follow]

These are the best personal questions to ask your best friend. This way you can get to know each other better, learn what makes you both tick, and from there your friendship can grow even stronger.

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Samantha Ann
My name is Samantha Ann. I am 28 years old. It was always my dream to become an advice columnist, so after years of off and online dating and eventually finding...