Friendship Questions: Enhancing Conversations And Bonding Over Memories

Having a thoughtful conversation can be a simple but powerful way to strengthen a friendship. By discussing your thoughts, feelings, wishes, and fears, you may learn to understand each other better while growing closer. How do you kick off this kind of enriching conversation, though? Often, the solution is simply to ask the right questions.

Below, you'll find a list of some interesting questions you can use to get to know your friends better—or to potentially make friends with someone you hardly know at all. Some are lighthearted conversation starters, while others are meant to open up a deeper exchange about the things that matter most in life. While there’s no “perfect question” that can guarantee a closer friendship, the topics listed here should help you get to know someone at least a little bit better than you did before. 

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How vulnerability and honest conversation can build a friendship

When you’re talking with a compatible person, this process can build on itself until you both wind up discussing the things that are nearest and dearest to your hearts or that make you feel vulnerable. Some of the closest and most rewarding friendships in life can be born out of this kind of communication. According to some psychologists, part of the reason humans seek friendship in the first place is because we want to find someone with whom we can express our authentic selves. The following friendship questions may help you reach that place of comfort and trust over time.

Pop culture questions

Discussions of books, movies, TV shows, music, and other forms of media can be an excellent “icebreaker” subject. When you’re not sure what to talk about with a friend, sparking a conversation about the things that most entertain them may help get things rolling. Examples of such questions include:

• If you were stuck on a desert island for the rest of your life with only one book (or movie, or TV show), which would you choose?
• What song do you most like to listen to when you’re sad?
• What song do you listen to when you want to get pumped up?
• If you had to appear on a reality TV show, which one would it be and why?
• What’s a movie that could have been great but was ruined by the ending?
• If you could pick one fictional character to be your best friend, who would it be?
• What piece of media that other people hate do you think is actually great?

What pop culture questions can tell you about a friend

Questions about TV shows and bands might seem superficial at first, but they can actually offer a sense of common ground while prompting deeper discussions. Powerful works of art often speak to a person’s most deeply held beliefs, longings, and fears.

Childhood memory questions 

Knowing where someone came from can sometimes tell you a lot about who they are now. Here are some questions to consider asking about a person’s early life:

• When you were a kid, what did you want to be when you grew up?
• What’s your favorite childhood memory?
• How did you find out that Santa Claus wasn’t real?
• What book or movie influenced you the most when you were younger?
• What was your favorite holiday as a kid?
• Who was the first person you became friends with?
• What did you like most and least about the place where you grew up?
• Who was your childhood hero?
• Who was your favorite family member as a kid?
• When did you first start to realize your parents didn’t know everything?
• How did you feel about school as a child?

Coming-of-age questions

You can follow up your discussion of childhood with questions about adolescence and young adulthood, which may reveal even more about how your friend became the person they are now. Examples include:

• What was the worst trouble you got into as a teenager?
• What fashion trends did you love that make you cringe now?
• What was your AIM screen name (if applicable)?
• What did you study in college (if applicable)?
• What was the first concert you went to?
• What’s your favorite memory from high school or college?
• What’s the craziest adventure you’ve had?

What an adolescent or childhood memory can tell you about a friend

The way people think about their life stories may be a core feature of their identities. By learning more about where your friends came from and how they got here, you may better understand how they see themselves. 

Time travel questions

Many fun conversation starters involve hypothetical scenarios about what a person would do if they could interact with the past or the future. Possible questions include:

• What historical figure would you most like to talk with?
• What do you wish you could tell your younger self?
• What question would you ask your future self?
• If you had to travel to the distant past and could only bring one piece of modern technology, what would you choose?
• What historical event would you change if you had a time machine?
• If you could learn one thing about the future of humanity, what would it be?

What time travel questions can tell you about a friend

Along with prompting a fun chat about history and time travel paradoxes, these kinds of questions can be a chance to talk about your big-picture priorities. You can talk about what you value in today’s world, what you wish was different, and what hopes you have for the future. These may help you discover whether your values and curiosities align with your friend’s.

Bucket list questions

Asking about a person’s “bucket list”—the things they hope to experience in their lifetime—is a classic type of “getting to know you” question. Here are a few examples:

• What’s the one place on Earth you’d most like to see before you die?
• What do you most hope to accomplish during your life?
• Is there someone you wish you could reconcile with while you’re both still alive?
• Who do you most wish you could meet before you die?
• What’s an experience you hope to have during your lifetime?
• If you knew you were going to die tomorrow, what would you do today?

What you can learn about a friend from their bucket list

Many philosophers and psychologists have suggested that an awareness of mortality plays a significant role in how people understand the meaning of life. Reflecting on death can often trigger thoughts about your most significant priorities, so talking about them with a friend can be a deep bonding experience.

Questions about vulnerabilities

Questions about the things that make a person feel scared, sad, embarrassed, or otherwise vulnerable can be the most difficult to ask and answer. However, they may also be among the most valuable ways to build stronger friendships.

Learning the answers to some of the following questions may deepen your bond with your friend. Just remember to respect their boundaries if they don’t want to discuss or share about a certain topic:

• What’s your biggest fear?
• What would you change about yourself if you could?
• What’s your most embarrassing experience?
• Which family members do you have the most difficulty with?
• What are you struggling most with right now?
• What’s the weirdest thing you believe?
• What is your biggest regret?
• Do you have a guilty pleasure?

What questions about vulnerabilities can tell you about a friend

While the conversations prompted by the questions to ask listed above may be difficult, they can show you a side of your friend they don’t show to the rest of the world, which can be a powerful source of intimacy. In addition, they may help you better understand how to support them through difficult times in the future. 

Self-definition questions

The following questions can help you get a better sense of how your friend sees their own identity:

• Are you a night owl or a morning person?
• What’s your favorite season and why?
• Are you a “Type A” or “Type B” person?
• If you were an animal, which one would you be and why?
• What’s your greatest strength?
• What do you wish people understood about you?
• What goals are you working toward right now?
• If you had one extra day every week, what would you do with it?
• What was your proudest fashion moment? 
• What’s your biggest accomplishment?
• What are you most thankful for?
• Who do you think has been the biggest influence on your life?
• What’s the best compliment anyone’s ever given you?
• Which of your parents or other relatives are you most like?
• What do you think is most important in life?
• What would be your perfect day?

What self-definition questions can tell you about a friend

People may not always see themselves with perfect clarity. Still, understanding what your friend thinks about themselves can often help you learn a lot about their behavior, emotional responses, and motivations. 

Want to feel more secure in yourself and your relationships?

Talk it out with a therapist

How a conversation with a therapist could help your friendship

If you’re concerned that you’re not as close with your friends as you’d like, prompting a deeper conversation with them may help. However, discussing what you’re feeling with a mental health professional might also be a good idea. 

Persistent worries and insecurities about your relationships can sometimes be an indicator of anxiety, which therapy could help you address. Working with a counselor might also help you build self-esteem and confidence, which can make it easier to be vulnerable and responsive when talking with the people you care about. 

Not everyone feels comfortable talking with a therapist about these kinds of challenges face-to-face, which is why many turn to online therapy instead. Internet-based treatment can create a sense of distance, control, and comfort that can sometimes make it easier to open up and participate in the therapeutic process.

Current evidence indicates that online treatment can be an effective way to treat persistent worries, self-esteem difficulties, and many other common obstacles to connecting with others. For example, a 2020 meta-analysis of 20 different trials suggests that online and in-person cognitive behavioral therapy “had an equal effect” on clients with social anxiety, with both methods producing significant reductions in symptoms.