100 Questions to Ask Friends for a Stronger Bond

While we can never know everything about someone, we can learn more about individuals by having questions to ask friends to deepen the bond. Our friends are often our chosen family and are with us for our biggest wins and the hardest part of life. There is no such thing as knowing everything there is to know about a person.

However, learning more about each other is a great way to deepen your connection and become a better friend. One of the best ways to learn more about each other is to ask personal questions or fun questions that teach us new information about our friends so ongoing connection-building can happen as we continue to spend time with each other.

Healthy communication helps create a strong bond, from an early positive influence to a life-long friendship that survives many challenges. The more we learn about each other and establish that we are a safe space for each other, the more rewarding and exciting the relationship will be.

This article will outline some questions that you may consider asking your friends. They range from deep questions to ask a best friend to silly questions to ask friends that you may want to get to know better. If you need a conversation topic, this article may come in handy from dinner parties to happy hours to first dates.

Benefits to Asking Questions

Before diving into the questions, it can be helpful to understand some of the benefits that you can receive by asking questions and creating a stronger bond with your friends. When you understand these benefits, working questions to get to know or understand another person better will become a priority and eventually a habit, taking many of your relationships to the next level.

Deeper Connection

The biggest and likely most obvious benefit is that asking questions with your friends will help you to develop deeper connections and understand one another better. Even if we have known a person their whole lives, we may never have the chance to understand their thoughts and motivations like we will if we take the time to ask. Having those conversations will often help you develop more compassion toward a friend when you understand deeper parts of them.

Chances to Share

Another benefit to asking these questions is allowing your friends or acquaintances to share more about themselves, which people love to do. By providing the space for them to share and connect with you, you also create a space where you are comfortable diving into topics that would not be accessible otherwise. This again leads to a deeper bond and connection.

Mental Health

The final benefit we will discuss is working through these questions to ask friends allows you to check in on your friends’ mental health in a more natural way. Many people are not able to process their emotions and feelings unless they are asked directly about them, either in response to the way they are acting or out of a natural check-in with a friend. By choosing to ask your friends about their lives and mental health, you allow them to share and even process some of the hard things that they may not be able to do otherwise.

Your mental health will likely also benefit from engaging in deeper conversations with your friends, and you may even be able to share in response, allowing you to describe your current state and where you would like to be moving forward. Getting to connect with others through deep conversations allows you to make sense of new people through unnatural life transitions and develop a healthy support system.

Silly Questions to Ask New Friends

When you are just getting to know someone, you are not quite ready to dive into the deep and difficult questions that you may be able to ask your best friends. However, there are still a whole host of questions to ask friends that you are still getting to know to understand them better. These can be silly questions, such as asking about favorites or how they spend their time.

They can also be questions aimed at moving the connection from an acquaintance to a friend that you feel comfortable with. Some of these can also be great icebreakers for a group of people just getting to know one another.

Learn About Their Favorite Things

Getting to know a person’s favorite memories or time of the year can help you find more things that you have in common and can even create traditions for friends as you continue to get to know one another. Asking a friend questions about their favorites will help you understand them better.

What is your favorite season and your favorite activity to do during it?
What is your favorite color and how do you incorporate it into your life?
What is your favorite podcast to listen to on a long car ride?
What is your favorite meal to make for other people?
What is your favorite game to teach people?
What was your favorite subject growing up and how did it impact what you do now?
What is your favorite food that you can eat over and over without getting sick of it?
Who is your favorite book character? Who do you identify with most?
What is your favorite holiday to celebrate and why?
Which Halloween costume was your favorite ever?
What is your favorite memory of a birthday party for you or someone you care about?
What is your favorite movie that annoys others when you watch it?
What is your favorite form of vacation transportation?
What are your favorite fashion trends and would you wear them?
What is your favorite class you’ve ever taken?
Which social media app is your favorite to use?
Did you have a favorite cartoon character growing up?
Did you have a favorite childhood pet? What was their name?
Tell your favorite “dad joke” that always makes you laugh.
Where was your favorite meal you’ve ever eaten?

Random Questions to Break the Ice

When you are in a group of new people, it can be helpful to ask some questions to break the ice and start getting to know one another past the initial introductions. These are some silly and fun questions to help you get to know the group better.

Are you an early bird or a night owl?
Where is the most awe-inspiring place you have ever been?
Tell me a silly item on your bucket list.
Describe your biggest pet peeve and the typical reaction you have.
What three words would your friends describe you as?
What fashion moment do you wish you skipped out on now?
What did you name your imaginary friend when you were a child if you had one?
What is the weirdest thing you thought was cool as a child?
What was your aim screen name and how did you come up with it?
What is the best advice you’ve heard and how did you implement it?
Who played at the first concert you remember going to?
Describe the ideal friend weekend and what you would do.
Who was your first celebrity crush? How do they relate to your current relationships or partner?
What’s the best gift you’ve ever been given and why was it important?
If you could start a business, what would it do or sell?
If you threw a dinner party, who would you want there, and what would you serve?
How do you take your eggs?
What would you do if you won a Megamillions jackpot?
Which holiday do you think is the most overrated and why?
What is your ultimate comfort food?
If you drink, what is your go-to cocktail or drink order?
If money was not an object, where would you travel? Where would you live?

Interesting Questions to Transition from Acquaintance to Friend

These questions will dig a little deeper to help you get to know someone better and how they work. These are more personal questions than the icebreakers above, but they are not so deep that they will scare away someone who is not ready to go there yet. These are also good to ask on a date if you are trying to get to know a potential partner better.

What is the most exciting adventure you have ever been on?
What is your biggest fear and how does it impact how you live your life?
Who was your closest family member growing up and are they still the closest?
What is your most embarrassing moment? Do you think it would still be embarrassing if it happened today?
What is your dream job, and are you on the career path to reach that goal?
Do you believe in love at first sight? Why or why not?
What is your current greatest accomplishment and how are working to beat it?
What words describe the person you look up to the most?
Have you ever had to stop talking to someone based on boundaries? What got you to that point?
What is one thing that you want everyone you meet to understand or know about you?
Is there a certain smell that immediately reminds you of a memory?
Describe your dream home and the people that fill it.
What would you be willing to wait in line for multiple days for?
What is the first thing that you notice about a person when you first meet them?
What is your idea of the perfect date?
Is there a conspiracy theory that you kind of believe?
What small things make you smile?
Would you want to be famous? Why or why not?

Deep Questions to Ask Your Best Friend

When you begin to ask your friends deeper questions, you will begin to learn more about how they got to where they are and how they see where they are headed. The questions that follow will help you reach that place with your friends and achieve conversations so ongoing connection-building continues.

Questions about Childhood

Learning about the childhood that our friends experienced can help us understand their reactions and the way they have learned to process the world. This is particularly important if you did not grow up together.

Describe your favorite childhood memory. What about it made it so special? Was it a person, a place, or an activity?
What would you tell your younger self if you could go back in time?
What is your earliest memory? How much of it can you see, hear, smell, taste, and feel to this day?
Which one of your friends got you in the most trouble growing up?
Where do you think your biggest pet peeves came from?
Did your family ever see a family therapist? Was it a good or bad experience?
What is a cultural tradition from childhood that you have continued to embrace as an adult?
When do you think your career aspirations started?
Who was your best friend when you were younger? Do you still consider them a best friend?
How would you have parented yourself differently? How are you implementing this when thinking about your younger self?
What was the worst injury you had as a child?
Did you play a sport or two as a child? What lessons did you learn from that sport?
What was the worst haircut you had as a kid?

Juicy Questions to Dig Deeper

These questions hit on aspects of a friend’s well-being and current development that help you understand motivations and how they make decisions. Understanding these aspects of a best friend can help you create a space to share and encourage each other moving forward.

How do you define success? Would you consider yourself successful based on this definition?
Does your life feel purposeful? What areas do you feel lack purpose?
How would you describe a supportive environment for you when you are working on a big project?
How do you define beauty? How can you shift that to include more things that you see in yourself?
What is the scariest thing on your bucket list? How can you take steps to achieve that goal?
Who makes you instantly light up when they walk into a room?
What do you consider your love language? How do you best feel loved by your friends and family?
What situation do you wish you could go back and change how you reacted to?
What three words describe the goals you have for the next five years?
How do you feel when you are alone?
What can I do to support you when you deal with uncomfortable appointments like women’s health or therapists dealing with healing body, mind, and soul?
Do you believe you can have more than one best friend or does that defeat the purpose?
If you were to create a “happy human playbook” to help others understand how to take care of you, what would be the top three things you need?
What are your top priorities in this season, and how and I create a supportive environment for you to accomplish them?
What is the most valuable part of our friendship to you?
What or who made you cry last?
What has made you feel challenged, and how did you overcome it?
Do you enjoy being challenged in work or life?
What is your biggest regret, and how do you deal with your feelings about it when it comes up?
What do you think or believe that happens when we die? Does that change how you live?
Do you want to have kids? If so, how many?
What’s the weirdest dream you’ve ever had and what was going on in your life at that time?
What are some accomplishments that we can celebrate for you that are not centered on romance and children?
What was the last lie that you told? Why did you tell it?
What was the last New Year’s resolution that you were able to keep? What about the goal do you think allowed you to keep it?
How do you handle conflict? How do you need others to respond to conflict?
When was the last time you laughed so hard you cried?

Final Thoughts

When you are looking for questions to ask friends, you can use this list to spark conversation and get your friends to talk more about themselves, allowing them to share more about their lives and what they hope for in the future. These questions to ask your friends will let you create deep conversations so connections can be formed and continue to form. I encourage you to continue asking questions to learn more about your friends.

To learn more about questions to ask friends, communication skills, conflict resolution, and more, contact ADR Times!

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Emily Holland

Contributing Editor at ADR Times

Emily is a recent graduate of Pepperdine Caruso Law.
While in law school, Emily served as an executive editor on the Pepperdine Dispute Resolution Law Journal and had the opportunity to learn about ADR from world-class professors of the Straus Institute for Dispute Resolution.

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