A good friendship involves growth, and part of that comes from staying curious about your friend. In this Today article, Mindpath Health’s Leanne Leonard, LMFT, provides questions that can help you deepen your bond with your friends. Dedicate an entire night to this list or start with a few funny standouts. 

75 questions to ask your friends to get to know them on a deeper level_Leanne Leonard, LMFT_Mindpath Health

One of the joys of friendship is that you continually learn more about each other. A good friendship involves growth, and part of that comes from actively choosing to stay curious about your friend.  

With that in mind, it’s important to know what questions to ask your friends to deepen your bond. The key here is not to interrogate your friend, but to open up a space to appreciate one another for who you are and want to be. 

“There is no such thing as knowing everything about a person, so ongoing connection building between friends helps to nurture and grow the relationship, especially through natural and unnatural life transitions,” says Leanne Leonard, LMFT at Mindpath Health. 

We asked experts to share their best questions to ask friends and compiled a list of our favorites below. Dedicate an entire night to this list, start with a few funny standouts or slowly chip away at the deeper questions when there’s a lull in conversation. As a result, you’ll see each other in a whole new light. 

Deep questions to ask friends

  • If you had a whole day where you could do anything you wanted, what would you do? 
  • What are you most proud of about yourself? 
  • What is your greatest accomplishment? 
  • What are you still hoping to accomplish? 
  • What do you want people to know about you? 
  • What do you need more of in your life? 
  • What do you need less of in your life? 
  • What do you feel has been your greatest “win” so far in your life? 
  • What three words describe what you’re most grateful for? 
  • Would you rather people perceive you as being kind, smart or attractive? 
  • How do you like to receive care? 
  • How do you cope when things get hard? 
  • What do you really care about? 
  • What really frustrates you? 
  • What keeps you up at night? 
  • Who sticks out as being an early positive influence in your life? 
  • Who is most important to you now?  
  • How did you feel about where you grew up?  
  • Was it a supportive environment? 
  • Who are you most like in your family? 
  • Who in your family do you struggle with? 
  • Is there a time when you did something that seems so out of character that most people wouldn’t believe it?  
  • What is the most trouble you’ve ever been in? 
  • Looking back on your life, who or what makes you instantly light up? 
  • If you could leave a “mark on the world” that preceded you, what would it be? 
  • What would you like to accomplish in life?  
  • What makes your life feel purposeful?  
  • What values are most important to you?  
  • If one wish of yours could come true, what would it be? 
  • If you could travel anywhere, where would you go? 
  • If you could meet anyone in the world, alive or deceased, who would it be? 
  • What brings you joy? 
  • What is the best piece of advice you’ve ever been given?

Fun (sometimes funny) questions to ask friends 

  • What movie or show do you keep rewatching?  
  • What makes you choose it? (See question above.) 
  • What was your favorite game as a child? 
  • Which book or movie impacted you most growing up? 
  • What’s your favorite childhood memory? 
  • What is your favorite memory? 
  • What is on your bucket list? 
  • What are two places you want to go before you die? 
  • What does your ideal friend weekend look like? 
  • What is the most exciting adventure you have been on? 
  • Where is the most awe-inspiring place you’ve ever visited? 
  • If you weren’t in your current profession, what would you be doing? 

Hard questions to ask friends

  • What is your worst memory? 
  • What fears do you experience?  
  • What do you find most challenging in your life right now? 
  • What is something that not many people know about you?  
  • What prevents you from sharing that part of yourself? 
  • How do you know when you can trust someone?  
  • What event has had a large impact on your life? 
  • If you lost a loved one, do you think you would come to me for support? 
  • If you lost your job, would you come to me for help? 
  • Have you ever stopped talking to a friend? 
  • Why did you stop talking to them? (See question above.) 
  • Has a friend ever stopped talking to you? 
  • What led to that happening? (See question above.) 

Personal questions about your friendship

  • What about our friendship is important to you? 
  • What do you value most in a friendship? 
  • In what ways do you feel supported in the friendship?  
  • In which ways do you not? (See question above.) 
  • In what ways do you feel trust within our friendship? 
  • What is your favorite trait in me? 
  • What’s your favorite part of our friendship? 
  • What do you most look forward to doing with me? 
  • What is your least favorite trait in me? 
  • What do you dread doing with me? 
  • What is one piece of advice you would give to me if you knew I wouldn’t get offended?  
  • What would you do if your partner didn’t like me? 
  • What would you do if your parents didn’t like me? 
  • Is there anything I can do to show my appreciation for your friendship that I do not already do? 
  • Have you ever kept a secret from me?  
  • What made it difficult to share? (See question above.) 
  • If we could only do one thing together before we die, what would it be? 

Read the full Today article with sources. 

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Leanne Leonard, LMFT

Dallas, TX

Leanne Leonard has over 20 years of experience working with individuals, couples, and families to resolve conflicts and improve the overall quality of life.  She is a very interactive, directive, and coaching-based therapist. She believes that one issue can affect all areas of an individual and conflicts should be addressed as a whole, not unilaterally. She always knew she wanted ... Read Full Bio »

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