50 Deep Questions to Ask Your Friends for Juicy Conversations

Our closest friends are a true lifeline—people who care about us, understand who we are at a core level, and who remain at our side through thick and thin. Cultivating genuine, fulfilling friendships takes real work, though, and often it starts by simply asking questions.

Beginning a relationship with lighthearted questions—usually focused around interests, hobbies, and their life—is the perfect place to start. But as you develop your friendship, it makes sense to start asking deep questions to engage on a whole new level.

If you lived in a college dorm, there's a good chance you've engaged in your fair share of deep conversations with friends already, and those may be some of your most cherished memories.

Read on to discover the importance of deep questions over surface level conversation topics, check out a list of questions to get you started, and some tips on initiating deep conversations with friends so you can strengthen your relationships.

50 Deep Questions to Ask Your Friends

These questions cover a variety of topics including childhood, relationships, personal philosophies, and more. Many of them should spark natural follow up questions and conversation. You know your friends best, so choose the questions that you think may generate the best conversations and won't make anyone too uncomfortable.

Some of these may seem lighthearted, but actually can lead to some of the most interesting insights into you and your friends' psyche.

Deep Questions to Ask About Relationships

These questions can help generate some interesting insights into how your friends feel about the relationships in their lives, and perhaps yield some insights into why you are good friends with them in the first place:

• What is the most important relationship in your life?
• What was your childhood like, and how is your relationship with your parents? 
• What does it mean to be a good friend to you?
• If your exes were all stuck in a room together, what would they say about you?
• Do you think there is one person out there that each of us are meant to be with?
• What's the most unconventional thing that can attract you to someone?
• What's the most petty dealbreaker that will instantly turn you off of a potential love interest?
• If you could change one thing about me, what would it be and why?
• What’s your approach to handling disagreements and conflicts in your relationships?

Deep Questions to Ask About the World

Everyone has their own opinions about what is right and wrong with the world. These questions can help you and your friends dig in on how you really feel, and why you feel that way. These kinds of questions could provoke some intriguing and enlightening—but friendly—arguments.

• If you could change one thing about the world, what would it be and why?
• What's something about the modern-day world that bothers you, and what’s something about it that brings you joy?
• What is your favorite place in the world to be?
• If you could choose any decade to live in, which one would you choose?
• What is one thing that society has lost that you wish we could get back?
• If you could erase one technological advancement from the world, what would it be?

Deep Questions to Ask About Life and Death

There are no bigger questions than those that address where we came from and where we're going. These are some serious topics, so be prepared for things to get heavy. As long as you're in a safe space, these questions will make for some fascinating conversation:

• What are your best and worst memories from childhood?
  
• What’s something that happened in grade school that really impacted who you are today?
• Do you believe in fate, or do you think we have control over our own destinies?
• If you could change one thing about yourself, what would it be and why?
• Do spirituality or religion play any role in your life? Why or why not?
• Do you regret the path your life has taken to this point?
• If you could live a different life, what would it look like?
• If you could erase the bad memories from your mind, would you?
• If money were no object, what would you do with your life?
• How do you want to be remembered?
• Do you have any secrets that would change your whole life if they became public knowledge?
• Would you trade a long life for a short life full of distinction and success?
• If you could relive one day of your life, which day would it be and why?
• If you only had 24 hours left to live, how would you spend it?
• If you could know the day of your passing, would you want to know?

Deep Questions About Success and Failure

Sometimes, our friends may be the people we are most jealous of. But they probably feel the same about you! These questions about success and the various paths our lives can take will help you put things in perspective:

• Where do you want to be in 10 years? Are you currently on that path?
• Are you satisfied with your current career trajectory?
• What are your biggest fears, and how do you cope with them? 
• What’s a challenge you’ve recently overcome or are currently facing?
• How do you define happiness, and what do you do to cultivate it in your life?
• What are the core principles that guide your decision-making and actions in life?
• Do you ever feel like a failure?
• What's your definition of success, and how are you working to achieve it?
• What is the most important lesson you've learned in the past year?
• What advice would you give to your younger self?
  

Deep Questions to Get Weirdly Philosophical

It's time to have some fun! These questions are best asked later on in the evening when everyone has loosened up a bit and is ready to say some things that nobody expects. At first glance, some of these may not seem like serious questions, but you will be surprised by how much insight you can glean from the answers you'll hear:

• Would you rather time travel to the past or future?
• What would your role be in the zombie apocalypse?
• What fictional world would you most want to live in?
• What skill is the closest thing you have to a superpower?
• If your inner monologue was a book, what genre would it be?
• If aliens came to Earth and you were the first person they saw, what would you do to communicate to them that you were friendly?
• If you could be famous, what would you most want to be famous for?
• What's the most morally questionable thing you would do for a lot of money?
• Who's your favorite Beatle and why? (Adjust as needed for your friends' musical tastes)
  

The Importance of Asking Deep Questions 

The key difference between surface level conversations and deep questions is that the former has a quick and dry answer while the latter invites both parties to explore the topic more deeply. For example, lighthearted topics might be around today’s news or what happened at work today, while a deeper conversation goes beyond the surface. 

Patel says deep conversations fulfill the following criteria: 

• Emotional
• Involve complex thought
• Require vulnerability
• Are only had with a select few close people
• Build emotional bonds and strong relationships
  

What Topics Are Considered Deep? 

Deep conversation categories run the gamut, but include:

• personal values
• life philosophies
• family dynamics
• interpersonal relationships
• dreams and aspirations
• fears
• challenges
• self-reflection
  

“Engaging in deep conversations with people allows us to develop empathy, increases our own mental wellness, and creates connections,” Patel explains. “It also has benefits of intellectual stimulation and increased positive emotions.”

What’s more, research shows that going beyond small talk tends to make people feel happier, even though it’s challenging to initiate these deeper conversations. A 2021 study found that people felt more connected to others when having deep conversations versus shallow ones.

Another study from 2018 found that when we have these deep bonds, it promotes self-esteem, improves life satisfaction, fosters a sense of belonging, and boosts both our mental and physical health.

Advice on Initiating Deep Conversations with Friends 

The 2021 study we referenced above was interesting in that it noted people’s desire to connect deeply, but acknowledged just how difficult it can be to start these conversations. 

The truth is that asking deep questions requires vulnerability from both parties. You’ll find, though, that once you start talking about these topics the other person will open up slowly, which leads to a snowball effect of continued relationship growth. But how do you get there to begin with?

“Create a space where one feels safe to share, make time, validate and establish rapport,” Patel says. “Ask questions about their values and perspective and actively listen without judgment.”  

Remember, asking deep questions is a two-way street, meaning that there’s give and take from both sides. Remain open to your friends’ responses, be willing to share your own thoughts and experiences, and respect any desire to end the conversation or switch to a new topic.