280+ Deep Questions To Ask in Any Situation

Colorful gradients symbolizing depth of relationships from deep questions

Life doesn’t come with an instruction manual — and neither do our conversations. 

But sometimes, especially when you’re first getting to know someone, it is no easy feat to get past the stale small talk into a deeper conversation.

Although it would be handy to have a deck of conversation cards in our back pocket at all times, deep and meaningful relationships often start with organic question-asking. 

Asking someone questions shows that we care about them and are interested in learning more about their lived experience. By taking the time to have meaningful conversations, we connect with people more deeply, have stronger relationships, and build communities that are able to uplift and support us.

Whether you’re flirting with a crush, learning more about your long-term partner, or just connecting with some new friends over a charcuterie board, here are a plethora of deep questions you can weave into your conversations.

You might also like: The Ultimate List of Ice Breaker Questions and The Ultimate List of Conversation Starters

The Best Deep Questions To Ask

Colorful gradients symbolizing depth of relationships from deep questions

Questions To Get To Know Someone Deeply

  • What do you love about yourself?
  • If there was anything you could change about yourself, what would it be?
  • Do you consider yourself an introvert or extrovert?
  • What is your relationship like with members of your family?
  • What keeps you motivated every day?
  • What do you enjoy most about your work?
  • What do you dislike most about your work?
  • Do you have any hobbies
  • What kinds of books do you like to read?
  • What music are you most into right now?
  • Did you have a favorite character from a show or movie growing up?
  • If you could create a perfect day, what would it include?
  • What are some of your biggest fears?
  • Have you ever conquered a big fear? What was it like?
  • Are you someone who likes surprises? Why or why not?
  • What is your zodiac sign? Do you follow astrology?
  • When was the last time you surprised yourself?
  • What is the best gift you’ve ever received?
  • What is the best gift you’ve ever given?
  • Do you have any nicknames? Is there a name you’d like to be called more often?
  • What are some of your favorite memories from the past year?
  • What are some of your biggest pet peeves?
  • Do you have a favorite color? Has it always been the same?
  • If you made just a little more money, what is one small luxury you wish you could add to your life? 
  • How would your friends describe you?
  • How would your parents describe you?
  • What kind of impact do you want to have on your community?
  • Would you consider yourself an animal lover? What is your favorite animal?
  • How do you cope with big feelings?
  • What are some accomplishments you’re really proud of?
  • Who are your favorite people in your life, and what are they like?
  • Who is someone you admire?
  • When was the last time you laughed so hard you cried?
  • Do you consider yourself religious or spiritual?
  • Do you have a favorite nonprofit that you support?
  • Do you believe in second chances?
  • What is the hardest lesson you’ve had to learn?
  • Would you consider yourself more of an optimist or a pessimist? 
  • What were some of your cringiest moments from your teenage years?
  • Are you easily embarrassed?
  • What are some of your core values?
  • Do you have any habits you think others might consider weird or unusual?
  • Do you believe in any conspiracy theories?
  • If you could choose the next U.S. president, who would it be?
  • Are you still friends with anyone from high school/your childhood?
  • What movies do you think everyone needs to see?
  • What do you really care about?
  • What’s something that reminds you of home?
  • Are you good at giving advice or feedback?
  • Are you good at taking advice or feedback?
  • Are you a morning person or night owl?
  • Did you have any pets growing up? Were you particularly fond of any of them?
  • Would you say you have a Type A or Type B personality?
  • If I asked you ‘who are you?’ how would you answer?
  • Where is your favorite place to go in the entire world?
  • What qualities do you admire about your parents?
  • What did you want to be when you grew up?
  • What’s a skill you want to build or a hobby you want to explore more?
  • Who is someone you compare yourself to?
  • How do you spend the majority of your free time?

Deep Questions To Ask Friends

  • What do you value most in our friendship?
  • What are your current priorities in life?
  • What has been on your mind recently?
  • What do you need more or less of in your life?
  • How can I best support you when you’re having a tough time?
  • How do you feel about where you grew up?
  • Are you happy where you are right now?
  • Have you ever gotten into big trouble? What happened?
  • If you could wave a magic wand and change anything about your life right now, what would it be?
  • What qualities do you look for in a good friend?
  • What does your support system look like these days?
  • What’s the best piece of advice you’ve ever received?
  • What is something not many people know about you?
  • Do you have any hidden talents?
  • What do you love doing together?
  • Have you ever kept a secret from me?
  • What do you wish people understood about you?
  • What really frustrates you?
  • What makes a day meaningful to you?
  • How do you like to rest and relax?
  • What is the biggest risk you’ve ever taken?
  • Would you ever change careers?
  • What decade do you think will be your favorite? Why?
  • What are some big dreams you have for your life?
  • Do you have any regrets? What are they and why?
  • How have your values changed over time?
  • What are your favorite personality traits in yourself or in others? 
  • What are you grateful for today?
  • What role does love play in your life?
  • How do you define true friendship?
  • How do you think we can create a more inclusive society?
  • What legacy would you like to leave behind for future generations? 

Deep Questions To Ask Your Partner

  • What do you want out of a relationship?
  • Do you want children? If so, what would be your parenting approach?
  • How is our relationship similar to your parents’ relationship?
  • What can’t you live without?
  • What are some goals you have yet to accomplish? How can I help you achieve them?
  • What did your childhood bedroom look like?
  • When you were younger, did you picture yourself ending up with someone like me?
  • What are some of your biggest insecurities?
  • What makes you feel confident?
  • What was one of our best kisses?
  • If you won the lottery, how would you spend the money?
  • What is your dream living situation? House, camper van, cabin?
  • What are some of your happiest memories from our relationship?
  • What kinds of adventures do you want to have with me in the future?
  • What boundaries are important to you?
  • Have I supported you in the ways you need? How could I do that more often?
  • How would you describe me to other people?
  • How do you imagine I describe you to other people?
  • What are the biggest lessons you’ve learned from previous relationships?
  • What has our relationship taught you so far?
  • What is your favorite feature of mine?
  • Where do you see us in 15 years?
  • How do you deal with conflict?
  • How do I deal with conflict?
  • When was the last time I made you laugh really hard?
  • What is your least favorite chore?
  • How do I make you feel loved?
  • What do you think are the biggest things we could both work on to improve our relationship?
  • If you thought I was making a bad decision, what would you do?
  • What do you need to forgive yourself for? 
  • Besides me, who do you turn to for advice?
  • What does retirement look like for you?
  • What do we argue about the most?
  • What songs make you think of me?
  • What was your first impression of me?
  • How do you want to be remembered? 
  • Is there anything you’ve always wanted to know about me?
  • What fictional couples remind you of us?
  • What is the best compliment I have ever given you?
  • Do you think we spend enough time together?
  • How has our relationship evolved since we first met?

Deep Questions To Get To Know Your Crush

  • What’s something that always makes you smile?
  • Would you consider yourself a flirt?
  • What do you look for in a relationship?
  • How would you describe your sense of humor?
  • What are you passionate about? 
  • What qualities do you value most in a person?
  • What are you curious about?
  • Do you have a favorite quote or affirmation that inspires you?
  • Would you say you like to take risks and step out of your comfort zone?
  • What’s a life lesson you’ve learned recently?
  • What is your favorite way to connect with other people?
  • What’s your idea of a perfect date?
  • In what ways do you think we’re similar?
  • Did you vote in the last election? 
  • What are some causes you care about?
  • When is your birthday? How do you like to celebrate?
  • Do you prefer to plan ahead or be spontaneous?
  • What were you like as a kid? How have you changed?
  • Have you ever had your heart broken?
  • Have you ever broken someone’s heart?
  • How do you resolve conflict?
  • What is something you’re unwilling to compromise on?
  • What’s the worst thing about dating these days?
  • What’s something you want to do differently in your next relationship?
  • What is your relationship with your mental health
  • What is the most romantic thing someone has ever done for you?
  • How do you know if someone is right for you?
  • What is the perfect way to ask someone out?
  • What goals are you working toward right now?
  • What artist could you listen to on repeat?
  • What meal can you cook the best?
  • Do you have a lot of friends or a small circle?
  • What do you like to do when you’re bored
  • Do you collect anything?
  • What’s your worst habit?
  • What three items would you want to have if you were stuck on a deserted island?
  • Who is one person you can talk to about anything?
  • Have you ever kept a journal or diary?
  • What is a piece of art or media that has meant something significant to you?
  • What’s the craziest thing you’ve ever done? Would you do it again?
  • What do you think about when you’re by yourself?

Deep Questions To Ask a Guy

  • What were your past relationships like?
  • Do you have any strong opinions about Taylor Swift?
  • If you were a superhero, what would you want your powers to be?
  • If you were a woman for a day, what would you do?
  • Did you play sports growing up?
  • Do you ever feel pressured to not show emotion? How has that impacted you?
  • How do you build friendships with other men?
  • What do you think about society’s idea of what a man should be?
  • When was the last time you experienced privilege as a man? What did you learn from it?
  • How would you define your relationship with masculinity?
  • What is your relationship like with your parents?
  • What are your thoughts on chivalry? 

Deep Questions To Ask a Girl

  • What are some times that you’ve experienced sexism in the world? How do you wish things were different?
  • What’s your relationship like with femininity?
  • Do you ever want to be a mother? Why or why not?
  • What is the best depiction of womanhood in film or TV?
  • If you were a man for a day, what would you do?
  • Who is an empowering female figure in your life?
  • What makes you feel empowered and confident?
  • Do you ever feel pressure to present or look a certain way? How has that impacted you?
  • What do you think about society’s idea of what a woman should be?
  • What is your favorite thing to do in your relationships to other women?
  • What kinds of actions make you feel safe and supported by men?
  • How do you want to balance responsibilities in a relationship?

Deep Questions About Life

  • What do you think your life’s purpose is?
  • Do you have a hunch about how you will die?
  • If you could see the future in a crystal ball, what would you want to know?
  • How do you think you’d be different if you were raised in a different family?
  • What do you think makes a meaningful life?
  • What would you do if you found out you had six months to live?
  • What are you holding onto that might be holding you back?
  • Do you “work to live” or “live to work?”
  • How do you measure success?
  • If you restarted your life from the very beginning, do you think you’d still end up here?
  • What actually gets you out of bed in the morning?
  • If you had to describe this year of your life with only one word, what would your word of the year be? 
  • What can you do today that you weren’t capable of a year ago?
  • What would you do differently if you knew nobody would judge you?
  • What is the difference between really living and just existing?
  • When you are 80 years old, what will matter to you most?
  • What do you want most out of life?
  • Where do you find inspiration?
  • What do you want to change most about the world?

You might also like: The best quotes about life

Other Good Questions to Ask

Philosophical Questions

  • What is the meaning of life?
  • Do you believe in free will, or are the outcomes of our lives determined by external factors?
  • Can you truly know anything with absolute certainty?
  • What do you think is your purpose in life?
  • How do we define and understand our identities?
  • Do you think people are inherently good? 
  • What do you think happens when we die?
  • Do you believe in an afterlife?
  • What is the relationship between past, present, and future?
  • Do you believe in good and evil?
  • Who decides what’s right and wrong?
  • Does the “truth” exist, or is everything just subjective?
  • What is important enough to go to war over?
  • Is stealing to feed a hungry person wrong?
  • Would you ever give up your life to save someone else?
  • What moral rules should we all follow?
  • What makes a person worth saving?

Icebreaker Questions

  • What is your most-used emoji?
  • What fictional family would you most like to join?
  • What is the best thing about being you?
  • What is the best joke you know?
  • What is your go-to karaoke song?
  • If you were a dog breed, what dog breed would you be?
  • What is one item on your bucket list?
  • What is your favorite place you’ve traveled to? 
  • What is the best romantic comedy?
  • What was the last thing you ate?
  • What is your #1 recommendation in this city?
  • You no longer have to work. What would you do on a Tuesday?
  • What person from history would you create a monument of?
  • Who is the most famous person you’ve ever met?
  • How would you describe your job to a little kid?
  • What was your first online screen name?
  • Of all of the fruits in the world — which one is the worst? 
  • Show me your phone wallpaper. Is there a story behind it?
  • What season would you be?
  • What is your favorite scent?
  • What snack do you get at the movies?
  • Are you a good dancer? Bust a move!
  • What is one thing someone would never guess about you?

Deep Would-You-Rather Questions

  • Would you rather be happy and know nothing or worried and know everything?
  • Would you rather be famous or forgotten after your death?
  • Would you rather be stronger or smarter?
  • Would you rather go through life unable to forget anything, or unable to remember anything?
  • If money wasn’t an issue, would you rather spend the next decade as a student or as an employee?
  • Would you rather be immortal, or live naturally?
  • Would you rather change the past or the future?
  • Would you rather be 90 years old or 9 years old for the rest of your life?
  • Would you rather talk to animals or be fluent in all languages?
  • Would you rather marry the person of your dreams or have the job of your dreams?
  • Would you rather know how you’ll die, or when you’ll die?

Thought-Provoking Questions

  • What makes human beings connected?
  • Do people have souls?
  • Would you break the law to save someone you love?
  • Which is worse: Failing or never trying?
  • Is it more important to love or be loved?
  • If you had the chance to go back in time and change something, would you do it?
  • What stands between you and happiness?
  • Can there be happiness without sadness?
  • Do you own things or do your things own you?
  • How would you describe freedom?
  • When have you felt most like yourself?
  • What do you owe yourself?

Article Details

September 1, 2023 1:16 PM
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