210 Deep Questions to Ask for a Closer Connection

Enhance your friendships and relationships with these conversation starters.

September 22, 2023

two men having a deep conversation outside — Dumblin Films/Shutterstock

Embarking on deep conversations with your friends, loved ones, and especially new people isn't always easy, but you'll be doing yourself a disservice if you don't ever try to dig below the surface. According to a 2021 study published in the Journal of Personality and Social Psychology, having more meaningful exchanges with strangers can actually improve our wellbeing. And asking the right questions is the easiest and quickest way to establish that kind of connection. Way back in the '90s, psychologists Arthur and Elaine Aron even came up with a list of questions they thought would actually lead to love. Yet both this and the previously mentioned study found that we often underestimate how willing others are to get into more serious conversation topics. So, if you want to swap out the small talk for a more personal interaction, keep reading. We've put together a list of deep questions to ask your friends, family, coworkers, and crushes.

Deep Questions to Ask Your Crush

Man and woman having tea at a cafe — Octa corp/Shutterstock

Have you ever regretted something you didn't say or do?
How many of your friends would you trust with your life?
What's your favorite childhood memory?
What makes you feel secure?
How do you balance future planning with the need to be spontaneous and live in the present moment?
What's a life lesson that you've recently learned?
What are some things you've incorporated into your routine to help maintain or improve your mental health?
What was your favorite subject in school?
Do you consider yourself a spiritual person?
What's the biggest lesson you've taken away from past relationships?
What's your biggest pet peeve?
Are you a dog person?
Why did your last relationship end?
What's something you want to do differently in your next relationship?
How would you describe the perfect date?
Do you easily pick up on body language?
What moral rules should we all follow?
What do you wish you did more of in your free time?
What do you think about society's idea of what a man should be?
How would your friends describe you?
Describe your perfect vacation.
How do you typically recover from a bad mood?
Where did you discover your favorite song?
Have you ever had your heart broken before?
Have you ever had a long-term partner?
Do you believe in soul mates?
Which one of your family members do you most enjoy spending time with?
What are the primary components of a happy life?
Would you break the law to save a loved one?
Excluding romantic relationships, who do you love?

Deep Questions to Ask Your Best Friend

Man and woman asking each other deep questions while drinking coffee — Branislav Nenin/Shutterstock

What's the biggest lie you once believed was true?
Is stealing to feed a starving child wrong?
If the average human lifespan was 40 years, how would you live your life differently?
What recent memory makes you smile the most?
How would you spend your ideal day?
What's the next item on your bucket list?
What's your greatest fear?
If you could go back in time and be born into a different family, would you?
What are the core values you believe in and try to follow?
How could I be a better friend?
How would you define the perfect life?
What's the most excruciating element of daily life?
What's the weirdest thing that's happened to you in the past year?
How would you describe freedom?
If you made just a little more money, what is one small luxury you would incorporate into the budget?
Do you think we see each other enough?
What would you change about yourself if you could?
What's the best way to relieve stress for $20 or less?
Have you ever kept a secret from me?
If you could wave a magic wand and change anything about your life right now, what would it be?
How do you define true friendship?
What's something you take a lot of pride in?
How are you tracking your personal growth?
What scrambles your brain every time you think about it?
What's been your greatest accomplishment?
Has someone else's pain ever given you joy? Be honest.
What decade do you think will be your favorite? Why?
What positive changes have you made in your life recently?
If you had a friend who spoke to you in the same way that you sometimes speak to yourself, how long would you allow this person to be your friend?
What's something you'd like to change about your personal life?

Personal Questions for Friends and Family

little girl thinking of deep questions to ask her mother at the kitchen table — Kleber Cordeiro/Shutterstock

What's something you know you do differently than most people?
What was the most defining moment in your life during the past year?
Can you describe your life in a six-word sentence?
What's one thing you wish you could go back and tell your younger self?
Do you believe in free will, or are the outcomes of our lives determined by external factors?
What's your favorite place to go to in the entire world?
Are you still friends with anyone from high school?
Do you think all the damage human beings have inflicted on the planet is worth the amount of progress we've achieved as a species?
What's the best gift you've ever given?
What makes a person worth saving?
What's a lame joke that you use regularly?
What quote resonates with you more than any other?
When was the last time you cried in front of another person?
What's the craziest thing that you've ever done? Would you do it again?
Do you have one dream that you've never been able to forget or that keeps repeating?
What important lesson have you learned from a friend or family member?
Who would you want to be stranded with on a deserted island?
Are you most pessimistic or optimistic?
What's something people always get wrong about you?
How do you feel about the way you grew up?
What do you want people to know about you?
What's one skill you wish you had?
If you could have anybody else's life, whose would you take?
If you could be president for an hour, what is the one thing that you would change?
What does personal growth mean to you, and how do you actively pursue it?
What's one behavior you could change that would help improve your personal relationships?
If you had the chance to go back in time and change something major in your life, would you do it?
If you died tomorrow, how would you be remembered?
Is there a simple fact about life that you wish more people understood?
What's your favorite true story that you enjoy sharing with others?

Bold Questions to Ask in the Office

Man and woman professional having a serious conversation while walking — mentatdgt/Shutterstock

What is the number one quality that makes someone a good leader?
How do you deal with someone in a position of power who wants you to fail?
How do you define success?
How well do you know your coworkers?
Describe your dream job in three words or less.
How do you approach new challenges or opportunities with the lessons you've learned from past experiences?
Which of your daily tasks do you enjoy most?
Do feel comfortable approaching leadership?
Do any of your hobbies coincide with any of your work duties?
What advice would you give a new hire?
What would you tell them about the company culture?
How do you recharge when you feel overwhelmed with work?
What quality in you would you hate to see emulated in your employees?
How do you think your coworkers see you?
Is job security a concern for you?
How well do your coworkers understand your job responsibilities?
Do you feel you have enough visibility with clients and coworkers?
Would like you to advance at this company or explore opportunities elsewhere?
How do you feel about pets in the office?
If it were up to you, would you be working in the office, remotely, or come up with a hybrid schedule?
In what ways do you incorporate creativity into your work?
Do you often find yourself working or worrying about work after hours?
What's your favorite day of the work week?
Do you feel like you have enough time during the work week for exercise and other things you enjoy?
Does what you're doing now have anything to do with what you went to school for?
What is the biggest risk you've ever taken in the workplace?
If you could swap jobs with anyone in the office who would you choose and why?
What is your biggest regret concerning your career?
Where do you find inspiration for new projects?
What's the most embarrassing thing that's ever happened to you in the workplace?

Thought-Provoking Questions to Ask Yourself

woman looking in the mirror — ShutterDivision.Shutterstock

What is the difference between living and existing?
Can there be happiness without sadness? Pleasure without pain? Peace without war?
In what ways do my friends and family influence who I date and spend time with?
How do I approach setting and working toward personal goals?
What role does self-reflection play in my everyday life, and how do I practice it?
If I died tomorrow, what would I regret not doing?
What is my life purpose?
What kind of parent would I be?
What's one quality I have that I'm proud of?
Am I a good listener?
How do I let my insecurities influence my behavior?
How happy am I right now?
How do I come across when meeting someone new?
If I were dating me, would I consider myself a good partner?
Is fear and anxiety holding me back in any way?
What's something I'd like to do more of?
What are some of my relationship deal-breakers?
What's something I've been putting off doing and why?
What does commitment mean to me?
What is my attachment style?
Do I like who I am and who I am becoming?
Who lights me up when I'm around them?
How do I honor myself?
In what ways could I be kinder to myself?
Who drains my energy when I'm around them?
What can I do today that I wasn't capable of a year ago?
Do I "work to live" or "live to work?"
What qualities do I look for in a good friend?
Is my love life where I want it to be?
What am I doing to secure a happy and healthy future for myself?

Deep Questions to Ask a Girl

two women having a serious conversation at a coffee shop — antoniodiaz/Shutterstock

Have you ever been "mansplained" by a coworker?
Have you ever asked a guy out on a date?
How do you feel about how women are depicted in television and film?
If you could only choose one, would you prefer to have pets or children?
How would you respond if your partner asked you to change the way you dress?
Would you stay with a spouse who has cheated on you?
In what instances do you think it's OK to be selfish?
What piece of literature, music, or film has influenced you most?
What's your favorite room in your house?
What's more important: Science or art?
What makes you feel most confident?
What is your favorite thing to do in your relationships with other women?
How has your idea of what you want in a significant other changed over the years?
Do you believe in fate?
What's the most out-of-character thing you've ever done?
What's your most annoying habit?
Do you have any concerns about aging?
When was the last time you experienced sexism?
What's your relationship like with femininity?
Do you like your name?
Who in your family do you struggle with?
Do you believe in second chances?
What do you need less of in your life?
How do you prefer to balance responsibilities in a relationship?
Do you believe straight people of the opposite sex can be platonic best friends?
What did you learn from your last heartbreak?
How do you feel about being the center of attention?
When was the last time you felt unsafe?
What do you think of the progress of the #MeToo movement?
Would you rather people perceive you as being kind, smart, or attractive?

Deep Questions to Ask Your Partner

man and woman talking to each other in their home — YAKOBCHUK VIACHESLAV/Shutterstock

What did your childhood bedroom look like?
Do you want kids?
What do you think will matter most to you when you're old?
Do you feel like money affected the way you grew up?
What's your favorite thing to do when you're alone?
What do you think your younger self would think about who you are today?
Is there anything from your past that you're ashamed of?
When do you feel most alive?
What's something your parents have taught you about love that you now realize is wrong?
What's your favorite thing about me?
What feeling have you been experiencing the most lately?
Are you feeling sexually fulfilled?
Do you feel jealous often?
How often do you experience anxiety?
Has a friend ever cut you off?
What's been the best phase of your life so far?
How have you changed since you've met me?
How do you like to receive care?
What's the worst quality you could tolerate in a partner?
What's the best household purchase you've made so far?
How do you think you would handle yourself in a long-distance relationship?
What do you think leads people to cheat in a relationship?
How do you react when you're upset? Is there anything you'd like to change about it?
Do you feel any pressure to be the provider in our relationship?
How can I be a better partner to you?
Is there anything about our relationship that you hope changes in the future?
What's the most difficult thing about being with me?
What is the most important commonality that we share?
What do you wish you had more of in your life right now?
How would you feel about me making more money than you?

Wrapping Up

That's it for our list of deep questions, but be sure to check back with us soon for even more ways to connect with the ones you love. You can also sign up for our newsletter so you don't miss out on what's next!

Carrie Weisman

Carrie Weisman oversees all SEO efforts at Best Life. She specializes in content optimization and editorial marketing. Read more

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Relationship Advice