21 Deep Questions To Ask Your Friends

“Close friendship is not something that is maintained all on its own, so these questions can make the work of doing that a little easier.”

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Deep questions to ask your friends about family, nostalgia, and goals.
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Whether you’re on a road trip together, or just tired of sitting in the same room and scrolling through TikTok, playing games like “20 questions” can lighten the mood and bring about some fun conversations. You may come up with some hilarious questions or answers, and entertain each other through even the dullest moments. If you feel like you’ve had your fair share of silly questions, you may want to consider deep questions to ask your friends.

While having fun and goofing off together is a great way to enhance a friendship, asking your friends meaningful questions can take your bond even further. “Asking deeper questions can bring you closer with your friends by building trust, especially if you end up sharing your thoughts first,” licensed mental health counselor Marc Campbell tells Bustle. When you’re vulnerable and show a genuine interest in your friends’ thoughts and feelings, they are much more inclined to do the same.

Asking deep questions can also help bridge a gap after conflict or distance. “Close friendship is not something that is established and maintained all on its own, so these questions can make the work of doing that a little easier,” licensed marriage and family therapist Chelsea Davis says.

Looking for examples of deep questions to ask your friends? Here are some ideas from Campbell and Davis (who are real-life best friends themselves!) to try.


What’s your favorite thing about our friendship?

Starting off with an uplifting, heartfelt question can ease each of you into a more vulnerable conversation. “It reinforces the positive aspects of your friendship, and it reminds both of you the reason why you actively choose to be friends,” Campbell says.

Davis also says this question can bring down walls that you or your friends might have previously built up when you’ve been hurt in the past. “Knowing that you always have [their] best interest at heart” is key, she notes. “That type of security is the highest form of intimacy.”


What is your biggest fear?

Everyone can relate to being afraid of something, so exchanging those fears with your friends can bring you closer and possibly teach you things about their experiences that you may not have known.


How’s your relationship with your family right now?

When you’re spending quality time with your friends, it can be easy to forget to check in with them about their other relationships. Familial dynamics can affect so much of people’s lives, so “[asking this question] can help you gain insight into why they are the type of friend that they are,” says Campbell.


How do you feel about the current state of the world?

Political events, global conflicts, and national issues can be overwhelming for most people to absorb. Try having an open and honest conversation with your friends about their perspectives on everything that’s happening. You might learn something new from their world views.


What’s your sweetest memory from childhood?

Plenty of “deeper” questions can be more serious or tough to think about, so consider mixing in a few nostalgic questions to lighten the mood. Swapping stories about happy memories from childhood is an easy way for you to learn more about your friend’s upbringing, and hear some significant memories for them that you didn’t know about before.


How am I doing as your friend, and how can I be a better friend to you?

It’s just as important to check in with your friendships as it is to check in with your romantic partnerships, Campbell says. Being receptive enough to ask for feedback on your role as a friend shows that you genuinely care, and can allow your friends to express any unspoken needs or concerns. “Most likely, you will find that your friend is having some of the same feelings and that can be incredibly validating and healing to the friendship,” says Campbell.


Who was the most influential teacher in your life?

Teachers don’t always have to be confined to a school setting; you might consider plenty of different role models or mentors to be your teachers. Most people who can quickly name an example of this are able to speak highly and in-depth about their favorite teachers in life. Getting to know more about the influential people who helped to shape the person your friend is now can be a sweet way to get closer.


If today was your last day on earth, who would you choose to spend it with?

If you know you won’t be offended if the answer isn’t you, this question can teach you a lot about the most significant relationships in your friend’s life. Ask them why they would choose that person, and you might be touched by how they feel.


What’s something you’re sensitive about that you wish no one would joke about?

While we all love a good roast session with our friends, there’s always the potential that some jokes may go too far. “The fun thing about roasting your close friends is its clever way of teetering on the line of truth and humor,” Davis says. “However, some things may sting more than others, so giving your friends the opportunity to create boundaries around sensitive topics can deepen trust and respect.”


If money wasn’t an issue, what career would you most want to pursue?

We all dreamt of certain “dream jobs” as children, and even in adulthood we all have passions that we may or may not pursue as a full-time career. There’s a chance you may already know the answer to this question, but even if so, it’s worth discussing those dreams with your friends — you just might have some in common.


Where do you see our friendship in 10 years?

Exploring each of your visions for the future can bring a sense of closeness and trust to your friendship. Knowing that your friends also see you being in their lives in 10 years is a great sign that you’re on the right path together.


What’s something about yourself that you wish other people noticed more?

Understanding the things your friends appreciate about themselves can tell you so much about how they want to be seen and appreciated by you, as well. “This question can uncover what we value and how we perceive ourselves,” Davis says.


How’s your heart?

As opposed to the usual “how are you?” asking this question digs deeper into what they’re feeling and experiencing. Even your most optimistic or successful friends might be hurting, so it’s important to check in with everyone from time to time. This is a great way to show you care not just about how your friends are on the surface, but about their internal world as well.


What’s something weighing on you right now?

Knowing that friends are always here to support and encourage you helps tremendously when you’re dealing with tough times. You can help ease that burden on your friends by digging deep into what they’re going through, and asking how you can help them get past it.


How do you like to be comforted when you’re upset, sick, or angry?

In the heat of the moment, whether you’re crying or feeling completely frustrated, sometimes it’s difficult to tell your loved ones what you need from them in terms of support. “This type of question can tap into each other’s love languages, which is a great way to explore one another’s needs,” Davis says. “We are all very different in how we like to receive and offer love [and[ support, so learning this about your friend shows that you can be depended on.” Asking this question at a neutral time can make you better equipped to handle your friends’ needs in the future.


When you spend time with me, do you ever feel pressured to spend more or less based on your financial situation?

Talking about money and finances with your friends can be hard, especially with the fluctuating economy, but it’s an important thing to discuss. Campbell suggests figuring out who’s taking care of what financially when you’re out with friends. “When you go out to drinks, who's paying? And when you get food, [would] you do a 50/50 split, things like that.”


Are my actions as a friend aligning with my expectations of friendship?

Friendship is a two-way street, and reflecting on your own behavior with your friends is an important way to cultivate a deeper bond with them. “Sometimes we get in our head and [think], ‘Oh, they haven't made plans with me in a month.’ Meanwhile, you haven’t made plans with them in six months,” Campbell says. To maintain a balanced friendship, “looking at yourself and seeing if you are trying to match your actions to your expectations” is a necessary step to take, he says.


Do you ever feel like I’ve crossed your boundaries?

Setting boundaries is a necessary step in any relationship: romantic, platonic, familial, or otherwise. Campbell says asking a direct question with specific examples to your friends is a great way to discuss their boundaries and your own. Asking questions about you and your friends’ routines and if they match or overstep their boundaries “gets into the power dynamics and the roles” of the relationship, Campbell says.


Do you want solutions right now, or do you just want to vent?

“I think it’s important to pose that question first,” Davis says. When a friend is upset, you should never assume what they need based on their issue. Asking this question is a great way to break the ice on how they’re feeling and show up as a supportive friend. “When you're just in a mood and you want to vent about what you're talking about, you really don't want to have unsolicited advice sometimes. And other times, you do,” Davis says.


How does social media influence your self-esteem?

Social media is an inevitable part of everyone’s lives, Davis says. And while it can be positive in so many ways, it can also negatively impact you and your friends. “I find that that's a lot of what people are talking about,” Davis says. “It's a lot of what mental health issues are surrounding.” Discussing social media habits with your friends can be a good way to understand your friends and their thoughts on self-worth.


If you could wake up tomorrow with only one thing different about your life, what would it be?

Everyone has an idea of things they would like to change about their lives. Asking this question of your friends can help you both get an idea of areas in their lives they might want to improve, and possibly figure out ways in which they can achieve that change. “This is a counseling question often used with clients to get to deeper issues and set goals,” says Campbell. “This is a good friendship question because it might tell you more about what your friends value.”


Marc Campbell, licensed mental health counselor

Chelsea Davis, licensed marriage and family therapist

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