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30 Deep Questions to Ask Your Best Friend & Strengthen Your Bond

Need deep questions to ask your best friend? Good. There is always more to learn whether you are new pals or already lifelong BFFs.

Deep Questions to Ask Your Best Friend

One of the best ways to continue to grow your connection and friendship with your BFF is with a list of the best deep questions to ask your best friend.

I don’t know about you, but my best friend and I tell each other everything. We have known each other for over 10 years, but we still have more to learn. There is no end to the bond between best friends.

Why you should ask your best friend deep questions

It might seem obvious. Deep questions bring people closer together. Sharing personal feelings, experiences, and fear enhances your trust and helps you understand one another better.

If you have a best friend that you never ask deep questions to, it does not mean the friendship is doomed to fail, but it can plateau and remain on the surface level.

With the help of deep questions and the answers to those questions, you can share so much more with each other and form an unbreakable bond. Or strengthen the one you already have. [Read: 15 signs of a best friend that prove you’ll never find someone better]

Deep questions to ask your best friend

Deep questions can range anywhere from your five-year plan to your greatest fear and beyond. And when your best friend is involved, there is really no limit.

Whether you are having a deep conversation or just randomly ask some of these questions while you’re out getting frozen yogurt, the answers and act of you asking will surely bring you closer together.

1. What does our friendship mean to you? 

This is a great place to start. You can dive deeper into what your relationship means and what you want it to mean. Do you have fun together, do you share everything? Or are you practically family? [Read: How to build lasting friendships in life]

2. Are you afraid of dying?

Although it is likely something we all think about time and again, it is very possible you’ve never spoken to your best friend about it. Sharing your greatest fears may not make them dissipate, but it can make you feel better to get it off your chest.

3. What do you think happens when you die? 

A follow-up question to the last is one we all consider. Is there a heaven and hell? Do we just disappear? Are we still connected to our bodies? Do we become ghosts? There is a lot to share here, and who better to discuss it with than your BFF? [Read: 5 unique traits that make a person trustworthy]

4. Do you want to have kids? 

Another personal question that would be inappropriate for the lady down the street to ask, but from your best friend, it tells you about the future and can open up a whole new side of your best friend. 

5. How is your relationship with your family? 

Again, you may see your best friend daily, but talking about the ins and outs of family dynamics is not the easiest, especially if things are on the fritz. Discuss where things are. Are they tense? Is there anything you can do to help?

6. Are you really over your last break up?

We all tend to put up a good front when we are in pain and reeling over a bad breakup. And although we stop talking about it before we stop thinking about it, it could still be very painful. Make sure your friend knows you are happy to let them vent.

7. What is your biggest regret? 

Do you already know your friend’s biggest regret? I don’t. But that is something that can certainly open up a different part of yourself. Think about your biggest regret, wouldn’t talking to someone you love and trust about it make it a little less heavy to carry around? [Read: 50 nice things to say to your best friend to brighten their day]

8. Who do you idolize the most? 

Oprah? Michelle Obama? Chris Evans? Harriet Tubman? And why? The person you idolize says a lot about the person you are and who you aspire to be. 

9. What makes you furious? 

Trump? People not recycling? Texting and driving? Your alarm clock? Your parents annoying you to get married and give them grandchildren? Who knows, you probably share a lot of the same pet peeves.

10. If you could go back to anytime in your life, when would it be?

I love this question, personally. Would your best friend go back to high school? Would they want to change things or just experience them again? [Read: Why your blunt bestie is a big boon in disguise]

11. Are you satisfied with where your life is right now? 

This can really open up a can of worms, but it is important to admit if you’re unhappy so you can do something about it. And if they are happy, celebrating that with the person you’re closest to means a lot. 

12. When was the last time you cried? And why? 

One of those deep questions to ask your best friend that can be quite sad is this one. Did they cry recently because they fought with their partner? Did they cry when they saw a baby at the store? 

13. Is there anything you would change about me? 

Do not ask this question if you are not prepared to hear the answer or answer it yourself. But, if this person is really your best friend, they likely know a lot about you, even the flaws, yet they still chose you as their best friend. So the answer couldn’t be too bad. 

As a matter of fact, I know my best friend would say if she could change something about me, it would be for me to take more risks and put myself out there more toexperience things more fully. That’s a pretty darn good answer if you ask me. [Read: 25 personal questions to ask your best friend and feel instantly closer]

14. Have you ever kept a secret from me? If so, why? 

I am not trying to start a fight here, but you likely are over whatever that situation may have been anyway. They most likely had a good reason for keeping something from you, or maybe they admit they were wrong and would have done some different if they could. 

Discussing stuff, you may have swept under the rug can make your relationship stronger. [Read: How to make your life better through friendship]

15. If you found out my partner cheated on me, would you tell me? And vice versa? 

This is something you should definitely discuss with your best friend. Personally, I always think honesty is the best policy, but knowing your best friend’s take on the situation is very important. 

If something were to happen, would they want to hear it from you or their partner? And would they feel comfortable telling you? 

16. Do you believe in ghosts, psychics, etc? 

I adore this question. As someone intensely intrigued by mediums and ghost sightings, this is always so fun to talk about. And it isn’t just about scary stories but lets you into your friend’s beliefs.

Do they think their family members are watching over them? Do they think psychics are real? Or are they super skeptical about the whole thing?

17. Are you afraid of getting old? 

So many people are afraid of aging. Whether it is the vanity, the health aspect, or just the fact that life is getting shorter, sharing this deep question with your best friend will guide you into the future together.

18. Is there anything you’re afraid you’ll never accomplish? 

Afraid you’ll never meet someone? Maybe your friend fears never traveling the world or being completely fulfilled at work. This question can lead to a pep talk from one another to make sure these fears are just fears and not realities. [Read: Best friend bucket list – 15 adventures for you and your BFF]

19. Do you believe in God? 

No matter your religion or lack thereof, sharing your belief system with your best friend can clue you into things you may know about each other but never fully understood. [Read: How to be a good friend – The friend code all BFFs must follow]

20. Have you ever not told me when you were upset with me?

This can help air out old wounds. They could be holding onto something from a long time ago, and this gives your best friend a chance to get it off their chest.

This is a great deep question to ask your best friend because coming out of it your friendship will be stronger.

21. What is your most intense memory?

You’ll notice I put most intense memory, not best. That is because your most intense memory, whether good or bad, impacts you a lot more than your happiest. 

This let you and your best friend really talk about your past and dive deep into the meanings of memories. [Read: Old love letters and memories – Should you keep them or throw them away?]

22. Who do you wish your relationship was different with?

Maybe they wish they were closer with their dad or grandparents. Or, perhaps, their romantic life isn’t what they want it to be. 

Talking about this and opening up about it is a great way to get closer to your best friend through deep questions and help them with something they are struggling with.

23. How do you wish the world were different?

I’ll bet there are tons of ways. They wish there were no more traffic, no more racism or sexism, and no more ridiculous robocalls. 

You can bond over your answers to this deep question. And, although these answers can be funny, they can get pretty serious.

24. Do you wish I was closer to the other people in your life?

Asking your best friend this deep question shouldn’t come from a selfish place. It is nice to know if your best friend wants to share you with their family and other friends. 

Do you hang out with just the two of you? Do they wish you were closer to their partner? Getting this answer can make your friendship even better. [Read: 19 ways to genuinely connect with others]

25. What movie from your childhood impacted you the most?

For me, it would have to be Mrs. Doubtfire, but for your best friend, this deep question could really get them thinking. Was it a cartoon? Perhaps it was something they watched with a sibling or parent.

Discussing this can even lead into a fun and nostalgic movie marathon.

26. What is the best gift you ever received?

You may hope it was from you but listen to what they say and their reasoning. This deep question to ask your best friend can really get them thinking. Maybe they got the most expensive gift from their partner, but when their grandma gave them a locket with their photos in it, it meant the most. 

27. Which family member do you think you’d be friends with if you weren’t family?

This is always a fun and deep question to ask your best friend. It is also a safe question to ask with someone you trust. It is no secret that we don’t like all our family members, even though we love them. 

So, which would your best friend choose to spend time with, even if it was in their genes? [Read: How to see the signs of toxic family members and cut them loose]

28. What language or languages do you want to learn?

I personally find this question so telling. And it isn’t just the answer, but the reasoning behind it. For example, does your best friend want to learn Italian so they can live there for a year? Or maybe they want to learn Spanish so they can communicate with their grandparents.

I’d like to learn sign language so I can communicate with people who are limited by who they can speak to. 

29. If we could go anywhere in the world right now where would you want to go?

Right this second. If you could just blink and be somewhere, where would your best friend want to go? Would they want to see the Eiffel Tower, or would they want to be home in bed, asleep? 

30. Is there anything you want to know about me?

I would presume that your best friend would be asking a lot of these questions back to you, but there may be something else they want to know. And being an open book with your BFF, you should be able to answer anything that came at you with.

[Read: How to create lasting memories with your best friend]

Using this list of deep questions to ask your best friend can only further enhance your friendship and strengthen your bond. So, go on and ask, the answers will be telling.

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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...