Deep Questions to Ask Your Best Friend

Friendship is a beautiful bond people share and with time, this bond becomes so strong that they begin to see themselves as best friends or “besties” as it is popularly known. However, it is important to know that beyond the chit-chat we have with our friends we should also get to know deep things about their likes, dislikes, fears, and aspirations -especially those they might not casually share with us.

So, if you are curious to know all about your best friend or to assess how well you know your bestie, ask them these deep questions below.

Deep Questions To Ask Your Best Friend

It is essential that you have background information about your best friend to a certain degree because knowing every tidbit about your friend helps create a special bond with that person. More so, indebt knowledge about your best friend will ensure the reduction of conflicts.

Below are some deep questions to ask your best friend that will help foster the growth of the friendship.


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1. What are you most afraid of?

Almost everybody has something they are afraid of – this is a common attribute of humans. While some have fears that they could probably laugh about, some people tend to be very cranky about their fears. More so, people tend to hide their fears to avoid being judged or mocked.

However, when one considers you as a best friend, sharing such information will not be a problem because it is only your best friend that will definitely understand your fears no matter how insignificant or enormous they might be. You should thus seek to know the answer to such a question if you consider someone as your best friend.

2. What are your life expectations?

This is another important and deep question to know if your best friend’s expectations are realistic or practical. Some people make and plan for unrealistic or unattainable expectations. This will indeed help you to be able to evaluate your best friend’s plans and how he intends to achieve them. You might even get to learn a thing or two from his/her answer or help them figure things out if they are uncertain about the future.

3. Who do you love the most, your father or mother?

According to research, sons tend to bond more with their mothers while daughters, on the other hand, seem to be more attached to their fathers. Although this might not be a hard and fast rule, your best friend might just fall on the bandwagon of such a classification. Better still, he or she might have a different perspective – with this question, you will definitely know who your best friend prefers and why.

4. What are your biggest regrets in life?

Sometimes people regret not following a career path, not expressing their feeling to a loved one, or not helping someone in need. The motive for asking this question could be to cheer him/her up and know some of the decisions that hurt him/her the most. This can be turned into an interesting conversation that will help you two get to know each other more.

5. How often do you visit the hospital?

We find persons not disclosing their medical records or history to people for many obvious reasons – sometimes even those closest to us might just hide this fact. If your best friend is suffering from one illness or another that they have not mentioned, this question will be the ice-breaker and given the bond of friendship you share, he/she will definitely confide in you once you ask.

6. How old would you love to live on earth before you die?

Death is inevitable as every human is destined to die either old or young, although people sometimes shy away from talking about death. This question is indeed a very sensitive one that can only be answered by a best friend. It doesn’t have to be a very serious conversation as you can as well have fun while talking about this.

7. Have you killed an animal before?

People that conserve wildlife advocate for the preservation of animals, especially animals that are on the verge of extinction. It is an important question to be asked since you would like to know your best friend’s position in relation to the killing or preservation of animals.

8. What would you like to be remembered for when you die?

Some humans aspire to leave lasting legacies before they die. The question is a deep one that will be answered after some long hard thoughts. The answer doesn’t have to be linked to something and you two can have fun sharing your dreams for the future.

Funny Questions To Ask Your Best Friend

Deep Questions
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Friendship creates a bond that makes it easy to be around someone and you will definitely not have a gathering of friends with no comic relief. Below are some funny questions to ask your friend that will also make you crack up!

1. What makes you laugh?

When we are happy and relaxed, we tend to laugh and smile a lot. More so, the company we keep can also determine how often we laugh and illuminates a positive feeling in us that is expressed through laughter. Ask your bestie this question to know exactly what triggers their happy and hilarious moments. You might also be in luck to know that you are one of the people that always make them laugh!

2. What is the silliest lie you have told someone?

People may lie in order to hide information he/she does not want you to know about. There are various other reasons why people tell a lie. Your best friend must have been trapped in the web of lies before and it would be nice to know the most frivolous lie he has ever told someone and how he managed to save his face – if he actually did.

3. When was the last time you hugged your parents?

Parents and their children sometimes share a special kind of bond, especially when they are very young. With this question, you will definitely get to know how fun-loving and carefree your bestie is – especially if he/she is fond of hugging his parents. If you are already adults, it gets more interesting to know their relationship with the parents at the stage.

4. What was your favorite toy as a child?

Childhood memories are always cherished when we become grownups; they are most times unforgettable events in our lives. Many children love toys and play with them and some grow up with memories of those toys still fresh. The question gives you an idea about your best friend’s fascination and the specific toy he liked as a child.

5. Can you eat raw fish if you are paid to do so?

This question is a hilarious one that sounds disgusting as well. Asking if your best friend can eat raw fish or not if the need arises will definitely elicit laughter. Well, if your best friend is Asain, this might not be such a hard puzzle to figure out as people from some parts of Japan and even Europe tend to eat a certain type of raw fish for its nutritional contents.

6. Can you ever work as a crossdresser?

There are cross-dressers who enjoy wearing male or female clothes for pleasure, but some actually earn a living from cross-dressing. Get to know whether your best friend will ever consider being a paid crossdresser with this question. This is also a funny way to bond with your best friend.

Questions To Ask Your Best Friend About Yourself

The bond of friendship in most cases is forged naturally. However, for it to flourish, both parties have to nurture it and a great way to do so is via conversation. When you get to have a chit-chat with your friend, a lot of things are clarified and the end result will be a deep bond forged by honesty, and love.

Some questions that can help you know how your friend interprets your actions or how well they truly know you have been listed below:

1. What do you like about me?

Knowing what a person likes or dislikes about you is important – it will guide you against doing things they do not like. It is important to know the things that attract your best friend to you and to make the friendship a long-lasting one, just keep doing the things they like about you.

2. Do you like the way I talk?

Talking is one of the ways we express ourselves and how we feel. While some persons know how to express themselves properly through their diction, others are unable to express themselves properly. Well, this could be a result of the fact that people have different personalities and they tend to exert who they are by way of speech. This is a simple but apt question to know what your best friend thinks about the way you communicate with him/her.

3. What do you like about my physique?

People have various body sizes, while some are tall and fat others might be short and slim. Knowing what your best friend thinks about the way you look is very important as it might prevent the person from body shaming you, especially if they are doing it unknowingly.

4. What do you like about my hair?

For most people, their hair speaks volumes about their hygiene and how they take care of themselves. It is will take some level of honesty to be objective while speaking or talking about a person’s hair. Response from our friends serves as positive or negative feedback to us on how to take proper care of our hair.

5. Do you think I am humble?

“Humility is a virtue” that is worth emulating, hence, it is important to know whether our best friend(s) actually attest to the fact that you are humble. This could be one of the reasons they are attracted to us. The question is important as people tend to think they are humble when those around them think otherwise.

6. Do you like the way I smile?

Everybody has a unique facial expression whenever they smile. It is important to note that smiling can be infectious and people tend to draw closer to people that tend to smile a lot. More so, know whether your smile is cute enough to brighten anyone’s day!

7. What do you dislike about me?

An objective and realistic answer to this question will inevitably be helpful and may make the person become a better person. Knowing what your best friend dislikes about you is actually a wake-up call to improve on your behavior because our best friends often tell us the truth even when it’s the last thing we want to hear.

8. What is your view about the shoes I wear?

The question reflects how fashionable your bestie actually thinks you are. More so, you will definitely get to know whether you need to upgrade your idea of ‘good shoes’, especially if you are a fashionista. Just ensure that you don’t take the criticisms too seriously because any answer given will help your appearance in public.

9. Do you think I am friendly to strangers?

Meeting new people can either start off on a good foot or not at all as strangers can be obnoxious, rude, or kind towards us. With this in mind, we should be careful when interacting with strangers offering the hand of friendship first won’t hurt. However, even though we might have good intentions, our actions might not correspond with our intentions. With this question, you will be sure to get an accurate response about how you interact with strangers.

10. Do I smell nice?

Every person smells in a unique way – the smell may be pleasant or unpleasant. Your best friend will definitely know if you smell pleasant or not – just take the response in good fate and improve your hygiene if there is any need.

Questions To Ask Your Boy Best Friend

Deep questions
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It is normal to see people of opposite gender becoming best friends. This kind of friendship is unique but can work perfectly if you are compatible. Several questions can be asked to get to know more about your boy best friend and we have compiled a comprehensive list below to help you with that:

1. Will you be spending your old age in the city or not?

Growing old is part of life and people will certainly become old if their lives are not cut short by death. It is also a phase in life that people look forward to and most times, those who have lived in the city for a very long time may want to retire to a serene environment. Finding out what your boy best friend plans for retirement is indeed the right step to getting to know them better.

2. Would you like your child or children to get married to mine?

You may want to enquire about ways to extend the arm of love and friendship of your boy best friend to your prospective children in the future. This may become possible when your children marry your boy best friend’s children or child but what does he think about this?

3. Where will you be traveling to for the summer holiday?

Holidays are periods you take some time off work or school and travel to another location or country to relax alone or with loved ones. Asking about his plans for the holidays will reveal whether he really prioritizes bonding time with his loved ones or not. More so, you might just land yourself an invitation to go on a vacation with him.

4. How many children would you like to have?

Having children comes with lots of responsibilities and the financial aspect is very demanding. Children should be taken proper care of and it is important that you are able to give birth to the number you are able to take proper care of. Ask this question to know whether he wants many kids or not.

5. What do you dislike about me?

People are generally attracted to their best friends for many obvious reasons. However, you may dislike one or two qualities or attitudes of your friend. Dialogue is very important as it will help you and your boy best friend talk about the things you dislike about each other.

6. What have you learned from me since we became best friends?

Learning is continuous – we are likely to learn one thing or the other every day, especially if we are always in pursuit of knowledge or intentional about growing our capacities. What are the things your boy best friend has learned from your months or years of interaction? He definitely must have learned some things – ask this question to find out.

7. Do you think I have chosen the right career?

This is an important question to ask your boy best friend about yourself, he should be objective enough to air his views about your career choice. The career path you follow may ultimately affect your income and general well-being – his response might actually make you rethink your decision if need be.

8. What is your dream car?

Boys are naturally drawn to cars, probably because cars are mostly part of the toys they get as toddlers. Through this question, you can learn about your boy best friend’s dream car and the reason or reasons for his choice. You may also get to know if he likes luxury cars or basic cars that are relatively cheap to buy and maintain.

9. What do you consider your greatest achievement?

It is only natural to rate one’s success in life to what he has been able to accomplish for himself. With this question, you will discover what your boy best friend considers his greatest achievement so far – whether it is material things money can buy or priceless things one cannot buy with money.

10. What do you do when you are bored?

Coping with boredom can be a very difficult thing to do, you may ask this question to find out how your best friend copes when he is bored. This question will also let you know about their hobbies, especially if they are shy to flaunt them.

Questions To Ask Your Girl Best Friend

Deep Questions
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Asking your best friend questions is also a step in the right direction to know her better, and share in her views, decisions, regrets, as well as likes and dislikes. The following questions will assist you to get the most out of your conversation with her:

1. What is your favorite perfume?

You can ask your girl best friend the perfume she loves the most in order to know the brand name she likes and why she wears them. This can help in your next quest to buy her a gift.

2. What is your favorite color?

Sometimes the color we like speaks volumes about our personality. You may want to find out the reason why she likes a particular color.

3. Have you been drunk before?

You may want to know if she has been drunk at some point in her life. More so, how well does she manage her behavior when drunk or does she just sleep it off till the next day.

4. What is that thing you can’t do without?

In as much as we know that humans cannot do without basic needs like food, water, air, clothing, and shelter, there are other things apart from our basic needs that we cannot do without. It could range from not leaving the house without wearing sunshades to going to the spa weekly! Whatever it might be, ask this question to know what your best friend holds dear to her heart.

5. Who was your first crush/love?

Falling in and out of love is part of life. Your best friend should have at least told you about their love life but if not, this question is sure to unravel her love life and how she fell in love for the very first time. The intention of asking these questions is to try to have a better understanding of who your best friend is and to strengthen the bond of your friendship. These questions should be asked in an interactive manner.

Tyna G
Tyna is passionate about sharing authentic news and giving her readers great content. Apart from writing, she is a music enthusiast who enjoys watching good movies

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