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Feb 14, 2022 · Asking your best friend questions is the best way to get to know them better, connect in a more meaningful way, and strengthen your bond with them.
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If you want to learn how to end the small talk and dig a little deeper into your personal or professional relationships, read our latest piece with 331 Juicy Questions to Ask Your Friends to Get to Know Them Better.
- Overview
- 50 Deep Questions to Ask Your Friends
- Deep Questions to Ask About Relationships
- Deep Questions to Ask About the World
- Deep Questions to Ask About Life and Death
- Deep Questions About Success and Failure
- Deep Questions to Get Weirdly Philosophical
- The Importance of Asking Deep Questions
- What Topics Are Considered Deep?
- Advice on Initiating Deep Conversations with Friends
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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.
Asking friends deep questions is important for developing a strong bond. It’s a great way to learn more about others, increase closeness between you, and have more interesting conversations. It is a healthy attribute of any relationship and can create emotional intimacy.
— REENA B PATEL, LEP, BCBA
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.
It's also important to first make sure that you would be comfortable answering the question yourself. Once you put someone else on the hot seat, it's only a matter of time before they turn the question back on you. Avoid anything that may be too traumatic or triggering, unless that is something you and your friends are all comfortable with.
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?
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?
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?
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?
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?
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
Reena B. Patel, clinical psychologist
Engaging in deep conversations with people allows us to develop empathy, increases our own mental wellness, and creates connections. — Reena B. Patel, clinical psychologist “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.
Reena B. Patel, clinical psychologist
Create a space where one feels safe to share, make time, validate and establish rapport. Ask questions about their values and perspective and actively listen without judgment. — Reena B. Patel, clinical psychologist 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. By Wendy Rose Gould Wendy Rose Gould is a lifestyle reporter with over a decade of experience covering health and wellness topics.
- Wendy Rose Gould
Dec 18, 2023 · We’ve compiled a list of questions for you as long as your friendship, ranging from the silly and saucy to the profound and thought-provoking. Call your best friend, get the giggles and gossip out of the way, and then ask away!
Jun 6, 2024 · We asked experts to weigh in on the best questions to get to know your friends better. From lighthearted to personal, these deep questions will help you build even closer bonds with your...
Dec 11, 2023 · Here is a list of good questions to ask your best friend: How does your perfect day look like? Plan from waking up to going to bed at night. How do you want to be famous? What type of emotion do you frequently experience? Who in life do you admire the most? Which experience in life has impacted your life the most?
Dec 30, 2023 · How well do you know your best friend, the person who has been with you through it all? Find out with these 175 deep questions to ask your best friend.
