85 Deep Questions To Ask Friends That Will Make Your Connections Feel Way Tighter

“Friendships are wonderful because unlike familial and deep romantic connections, friendships are entirely voluntary,” says Anna Goldfarb, author of Modern Friendship. Whereas literal genetics and your upbringing bind you to your relatives, and a legal contract might tie you to a partner, the only thing keeping you in a friendship is a mutual desire to be in it. “That's what makes [friendships] special, but that's also what makes them so vulnerable,” says Goldfarb.

Without the investment of a good deal of time and energy, friendships can fade just as quickly as they started—and there’s plenty of evidence to suggest that peoples’ friendships are indeed suffering right now. Based on data from the American Time Use Survey (a nationally representative survey of more than 200,000 people), the amount of time people engaged with friends IRL dropped² from 60 minutes a day in 2003 to just 20 minutes a day in 2020; do the math, and that’s a decrease of 20 hours of friend time per month. Unsurprisingly, that trend has coincided with a drop in close friendships and a rise in loneliness across the board.

Why we’re less deeply connected to our friends these days

Therapist Nina Westbrook, LMFT, founder of conversation card game Do Tell!, cites a couple societal factors that have pulled us away from deep social connection. “One is the continued rise of digital communication,” she says. “While cell phones and social media have enhanced the ease with which we can all communicate with one another, they can also hinder the development of more profound, in-person connections.”

Another reason for our fraying social fabric is hustle culture, adds Westbrook. “Expectations around productivity have led to demanding work schedules, which leaves less opportunity for people to nurture and sustain meaningful friendships.”

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Those who still manage to make time for IRL hangouts may also just be wary of getting deep… which can keep social connections feeling more like shallow acquaintanceships than the soul-baring stuff of close friendship. “We're usually hyperaware of how we're perceived, and sharing our true selves can feel awkward at times,” says Brittane Rowe, co-founder of the conversation game Hella Awkward. “Deep conversations take effort and vulnerability—sometimes we feel too busy managing our own stuff to delve into someone else's emotional depths.”

“Deep conversations take effort and vulnerability—sometimes we feel too busy managing our own stuff to delve into someone else's emotional depths.” —Brittane Rowe, co-founder of conversation card game Hella Awkward

Even if you do feel ready to upgrade a friendship from the small talk stage, it can be tough to know where to start. And that’s where having key questions on hand can help. It’s no wonder Pinterest reported an uptick in searches around “deep questions to ask friends” along with queries like “deep conversation starters” in its 2024 trend prediction report.

Why it’s worth asking your friends deep questions

While it may feel uncomfortable to get deep at first, vulnerability is an important ingredient in the formula for strong platonic connections, says friendship coach Danielle Bayard Jackson. “There’s something called the beautiful mess effect¹, which says we tend to like people more after they’ve been vulnerable with us,” she says. “It’s very endearing and humanizing.”

You may find that some friends welcome deep conversations when you first meet them, while others require more time to warm up to you. “There is no right or wrong timeframe of when to start asking your friends deeper questions,” says licensed therapist and friendship educator Blake Blankenbecler, LPC.

In any case, the payoff is likely to be worth your time and effort. Forming a deep friendship “lessens feelings of loneliness and offers a sense of belonging, connection, and more happiness,” compared to a more superficial or surface-level connection, says conversation expert Debra Roberts, LCSW, developer of The Relationship Protocol.

Though spending lots of quality time with a friend might naturally surface some deep topics of conversation, it also can’t hurt to arm yourself with conversation starters. Below, you’ll find 85 deep questions to ask your friends when you’re really trying to get to know them and strengthen your bond, courtesy of the above experts.

85 deep questions to ask your friends, from friendship and communication experts

On past experiences

What is a childhood memory that has significantly shaped who you are today?

Can you describe a moment in your life that challenged your beliefs and led to personal growth?

How do you navigate and learn from failures or setbacks?

Can you describe a moment when you felt truly understood by someone?

What's something you let go of that at one point you thought defined you?

What was your spiritual background as a child, and how does it impact your life today?

What were your childhood hobbies? Are they still a part of who you are?

When was the last time you forgave yourself?

What’s the most important lesson you learned from the job you hated the most?

What's the most memorable party you've ever been to?

What’s a regret that you have?

What was something that helped restore your faith in humanity?

If you had to travel back to one place you’ve already been, where would you choose, and why?

What’s an embarrassing moment at work that still lives rent-free in your head?

How would your childhood friends describe you?

If you could relive one moment in your life, which one would you choose?

What’s the best gift you’ve ever given?

What’s the best gift you’ve ever received?

Do you have any family traditions that are important to you?

Did you like the city or town you grew up in?

How did your family view mental health and therapy growing up? Is it the same today, or have their views changed at all?

In the past year, when did you feel the most joyful?

In the past year, when did you feel the most sad?

What were you like in middle school?

What would you like to tell your 16-year-old self?

On daily life

How do you cope with stress or difficult situations in your life?

What is a passion or hobby that brings you a sense of fulfillment and joy?

How do you express gratitude in your daily life?

How do you approach making decisions, and what factors do you consider most important?

Without mentioning any tech, what is your most prized possession?

Where are you when you're feeling your happiest?

Who would play you in the movie of your life?

What’s your idea of the perfect day?

Do you like to take risks?

What makes you laugh more than anything else?

What is causing you the most stress right now?

What's a bad habit that you wish you could quit?

Where do you feel the most safe?

What’s your favorite thing about what you get to do every day?

Which accomplishment are you most proud of?

When do you feel most like your authentic self?

If you had three extra hours in your day, how would you use them?

What’s your relationship like with money?

Which is hardest for you to say: "I love you," "I'm sorry," or "I need help?"

What’s something that you’re working through right now?

If time or financial resources weren’t an issue, what would you be doing with your life?

On relationships

What makes a friendship successful?

Who are you with when you're feeling your happiest?

How do you express and experience love in your relationships?

What's something you said or did in a previous friendship that you regret?

How do you handle disagreements or conflicts in your relationships?

How do you know it's time to move on from a relationship or friendship?

Are your parents still in love? Does it matter to you now?

What are your non-negotiables or dealbreakers in a friendship?

How can I better show up for you as a friend?

How many times have you been in love?

Do you believe in second chances for bad first dates?

What relationship advice would you give me?

How has your parent's relationship impacted your love life?

If you could teach your 15-year-old self anything about friendship, what would it be?

What do you think about your partner discussing your sex life with their friends?

Do you think my dating standards are too low, too high, or just right?

What’s been your biggest contribution to my life?

What kind of friend do you think you are?

What’s your relationship like with your parents?

How do you see yourself in your parents, and how do you not see yourself in them?

What were your friendships like in high school?

Do you think any of your younger friendships affect how you show up in friendships today?

On future goals

Are there specific goals or dreams you've yet to pursue, and if so, what's holding you back?

If you could travel anywhere in the world, where would you go, and why?

What is the one thing you want to do before the year ends?

What is something you’re too scared to go after?

If you could change one thing about yourself, what would it be, and why?

If you could ask your future self one question, what would it be?

If you could write a book, what would it be about?

If you had to live somewhere else, where would you choose and why?

On core values and identity

What cause is most important to you?

What is something that you feel people often get wrong about you?

Whom do you look up to?

What did you think of me when you first met me?

How would you describe yourself in three words?

Do you feel like you’ve found your life’s purpose?

What's more important: helping yourself or helping the world?

What are you passionate about?

What’s something that is really important to you?

What are two to three core values that guide your decisions and actions?