215+ Deep Questions That Make You Think Hard

Questions. They help you understand yourself, others, and the world around you. But what can you ask to truly make yourself think? We’ve compiled a list of the most thought-provoking, introspective, and engaging questions to ask yourself, your partner, and your friends—they’re sure to start a conversation in any situation.

The Most Thought-Provoking Questions

Do you love yourself?
What is your definition of happiness?
What do you want to be remembered for?
What’s the difference between living and existing?
What does it mean to be human?

Section 1 of 8:

Questions to Ask Yourself

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The best thought-provoking questions are ones that require more than a “yes” or “no” answer.^{[1]
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Research source} Don’t be afraid to ask yourself deeper, more difficult questions! After all, questions are the best way we can learn.^{[2]
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Research source} These questions can help you learn more about yourself and find out who you truly are:
- What book has had the most impact on you?
- Do you feel older or younger for your age?
- If the world was ending in a year, how would you spend your time?
- What lie do you tell yourself most often?
- What’s something you can do every day to feel good?
- What’s one memory that always makes you smile?
- If you could get a second chance at something, what would it be?
- What’s your favorite thing about yourself?
- What’s one thing you wish you could change about yourself?
- If you could be an animal, what animal would you be?
- What’s one thing you hope doesn’t change about you?
- If you could tell your younger self one thing, what would you tell them?
- What was the happiest moment of your life so far?
- If you didn’t have to work for money, how would you spend your time?
- What’s your worst habit?
- If you could have a superpower, what superpower would you have?
- Do you believe in ghosts?
- Do you find your relationships fulfilling?
- If you were to date yourself, what would you do?
- Do you love yourself?
- How do you communicate your feelings?
- What’s something you’re holding onto that you can let go?
- In what way are you your worst enemy?
- What do you do when people don’t like you?
- What is your greatest strength?
- What is your greatest weakness?
- What guides your decisions?
- What is your definition of happiness?
- What’s your biggest regret?
- What is your definition of beauty?
- What are your top 3 personal values?

Section 2 of 8:

Questions to Ask Your Partner

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Asking your partner or significant other deep questions can help you strengthen your relationship and learn more about each other. Plus, it’s an excellent way to see if you have common views, goals, and interests. And if you don’t, no worries! This is why talking these things out is important—you can truly see if you’re meant to be.^{[3]
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- Do you believe in love at first sight?
- Do you think cheating is justifiable?
- Do you believe in soulmates?
- How do you feel about our relationship?
- What are your expectations of me?
- What are your goals for us as a couple?
- Is there anything you’d change about our relationship?
- Where do you see yourself in 5 years?
- Who was your role model growing up?
- How do you feel about marriage?
- What’s your earliest memory?
- What past challenges have made you stronger?
- How do you want to be remembered?
- Who was your first crush?
- Do you want kids someday?
- How did your upbringing influence you?
- What are your personal hopes for the future?
- How do you handle stress?
- What motivates you?
- How do you like to spend your weekends?
- What’s one habit you’d like to change?
- What skill do you want to master?
- What’s the best advice you’ve ever gotten?
- What’s your dream job?
- If you started a business, what would it be?
- Who inspires you?
- What’s someplace you’ve always wanted to visit?
- What are your biggest fears?
- How do you express your emotions?
- What does emotional intimacy mean to you?
- What’s something you’ve never told anyone else before?
- How do you feel when we spend time apart?
- What does quality time look like to you?
- What values do you appreciate in others?
- How do you handle jealousy?
- What’s your love language?

Section 3 of 8:

Questions to Ask a Friend

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Getting to know your bestie better can be as easy as asking a wacky and wild question! Stay serious to strengthen your bond, or keep it silly with insane scenarios that make you both giggle. The more vulnerable you are and the more you open up with one another, the stronger your friendship will be.^{[4]
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- If you could have coffee with one person, dead or alive, who would it be?
- What’s your favorite movie of all time?
- How do you like to relax?
- What’s your favorite board game?
- What’s your favorite childhood memory?
- If you could learn a skill instantly, what would you learn?
- Who was your first celebrity crush?
- If you lived in a historical time period, what time period would you live in?
- What’s your most embarrassing childhood memory?
- What relationship made a big impact on your life?
- Do you ever feel lonely?
- What’s one thing you wish you could change about your past?
- What’s your go-to karaoke song?
- Would you rather explore the world or stay in one place?
- What’s your guilty pleasure?
- What’s your favorite holiday?
- Do you have any pet peeves?
- What’s the last thing that made you cry?
- If you could listen to one song for the rest of your life, what would it be?
- What’s your favorite midnight snack?
- What fictional character would you want to be best friends with?
- What’s the best surprise you’ve ever received?
- If you could live in a movie, what movie would you live in?
- Who’s your favorite celebrity?
- What’s your biggest red flag in a relationship?
- Do you have any regrets?
- What are you passionate about?
- What’s the top thing on your bucket list?
- What do you want to be remembered for?
- What’s your favorite part about your job?
- What’s something you’re proud of?
- What’s the biggest lie you’ve ever told?
- What app do you use the most?

Section 4 of 8:

Questions to About Life

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If you’re contemplating your life, don’t worry too much—we all do it at one point or another. But why not channel that contemplation and anxiety into something thought-provoking? The right questions can help you find understanding or even spark a breakthrough.^{[5]
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Research source} Ask yourself questions that bring hope, ignite change, or instigate development, like these:
- How long is now?
- What’s the difference between living and existing?
- If today was your last day on earth, what would you do?
- What worries you the most about the future?
- If we learn from our mistakes, why are we so afraid to make mistakes?
- What impact do you want to leave on the world?
- If life is so short, why do we do things we don’t like?
- Why do you matter?
- How do you know whether it’s time to hold on or time to let go?
- Are you happy with your life?
- What fears are holding you back?
- What’s something you’re proud of?
- Where do you expect to be in 5 years?
- What do you pretend to understand but really don’t?
- What big lesson could people learn from others?
- What do you want to accomplish before you die?
- What is worse than death?
- How short would life have to be to live it differently every day?
- What’s the easiest way to waste a life?
- If you won the lottery, what would you do?
- What is the meaning of life?
- What gets you out of bed in the morning?
- If not now, then when?
- Which is worse: failing or never trying?
- What’s your biggest dream?
- What do you want most?
- What does it mean to be human?

Section 5 of 8:

Questions to About the World Around You

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Curious about the world around you? Asking questions is a healthy way to stay curious, ignite creativity, and improve your overall thought process. Questions help us understand the world!^{[6]
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Research source} Targeting questions around happenings in the world can help you understand your own views better and become a more empathetic person.
- What do you think the world will look like in 100 years?
- Would society be better off without the internet?
- How would you describe the idea of color?
- How would you describe the idea of music?
- What do you imagine yourself doing 10 years from now?
- What’s something you can’t live without?
- What does it feel like to remember something?
- Is humanity good or evil?
- Do you believe in other worlds?
- Do you believe people can change for the better?
- How do you think people would react if the sun disappeared?
- What would people do if aliens attacked?
- What do you wish you didn’t know?
- What drains people’s happiness?
- If you didn’t know age, how old would you think you were?
- Do you work to live or live to work?
- What’s something you do differently from everyone else?
- Who decides what’s right and wrong?
- Do you think anyone is happy all of the time?
- Why do people chase success?
- Why do people do good deeds?
- Who do you compare yourself to?
- Would you break the law to save a loved one?
- What’s something you know you do differently than most people?
- What’s a lesson you’ve learned that’s impacted your perspective?

Section 6 of 8:

Deep Questions to About Reality

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Sometimes, reality is great, and other times, it has you wanting to escape into any other world. But why is that? Stay curious and contemplate what you know and what you don’t. Play around with societal standards and the psychological notions of why you are the way you are. It might just lead you to a new understanding.^{[7]
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Research source} These questions are not only great to ask yourself but can be excellent conversation starters:
- Would you rather lose all your memories or never make new ones?
- How do you measure success?
- If you restarted your life, would you end up in the same place?
- Is life a computer simulation?
- How can a single moment have the power to change everything?
- What if there were no experts and everyone knew a little about everything?
- If beauty is in the eye of the beholder, what about reality?
- How much influence does a person’s name have?
- Is time a construct?
- Is fate a real thing?
- Does the truth exist?
- What would you try if you knew you would fail?
- Is it more important to love or be loved?
- Is there such a thing as perfect?
- Where do thoughts come from?
- What will civilization look like in 2,000 years?
- What would happen if money didn’t exist?
- What do you think being famous is like?
- What is justice?
- What came first: the chicken or the egg?
- What’s holding you back?
- Is crying a sign of weakness or strength?
- Is it possible to lie without saying a word?
- When it’s all said and done, will you have said more than you’ve done?
- What’s important enough to go to war over?
- What is the last thing on your mind?

Section 7 of 8:

Funny Questions to Ask Anyone

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Who says thought-provoking questions have to be serious? Silly, wacky, and goofy questions are a great way to lighten any mood, bring people together, and make you think about things in a new way. So, ask your family members, friends, coworkers, or even strangers these interesting and curious questions to make them smile and think outside the box:
- What’s your favorite smell?
- How long would you survive a zombie apocalypse?
- What do you think your last words will be?
- If you were a dog, what breed of dog would you be?
- How do you hang toilet paper: over or under?
- What would you do if you won a million dollars?
- Why do round pizzas come in square boxes?
- What would you do if you could live forever?
- Do you like pineapple on pizza?
- Waffles or pancakes?
- Do people drink or eat soup?
- Do mermaids give birth or lay eggs?
- What’s the first thing you wash in the shower?
- How do you fold a fitted sheet?
- Who would win: Superman or Batman?
- What is the soundtrack of your life?
- Who would narrate your life in a movie?
- What’s your secret talent?
- Is a hot dog a sandwich?
- Is pizza an open-faced sandwich?
- Would you rather have bionic arms or bionic legs?
- What conspiracy theories do you believe?
- If you were a pizza topping, what would you be and why?
- What do you hate?
- Which meme best represents your life?
- Which color has the worst personality?
- What do you think ghosts sound like?
- If rainbows could talk, what would they say?
- If you could name a new state, what would you name it?
- Which role would you play in a reality TV show?
- Who would you switch lives with for a day?
- Do you think the internet can be broken?
- Why do cats have nine lives?
- Is ketchup a smoothie?
- Why do we get in a car but on a bus?

Section 8 of 8:

FAQs: Thought-Provoking Questions

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How does asking questions improve intimacy? Asking questions helps you connect with others. Intimacy is a feeling of closeness and connection, whether that connection is romantic or platonic. When you ask questions, you show that you want to learn more about someone. When you answer questions, you share a part of yourself with others.^{[8]
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Greater Good in Action
An initiative by UC Berkeley's Greater Good Science Center promoting science-based practices for a meaningful life

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What makes a thought-provoking question? A thought-provoking question makes you think. These types of questions make you more aware of your identity, learning style, and overall approach to life. They allow you to challenge yourself and grasp a better understanding of the world.^{[9]
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- Thought-provoking questions are often difficult to answer—they’re meant to be a challenge! The harder you have to think, the better.
EXPERT TIP

Lena Dicken, Psy.D
Clinical Psychologist
Dr. Lena Dicken is a Clinical Psychologist based in Santa Monica, California. With over eight years of experience, Dr. Dicken specializes in therapy for anxiety, depression, life transitions, and relationship difficulties. She utilizes an integrative approach combining Psychodynamic, Cognitive Behavioral, and Mindfulness-based therapies. Dr. Dicken holds a BS in Integrative Medicine from the University of Hawaii at Manoa, an MA in Counseling Psychology from Argosy University Los Angeles, and a Doctor of Psychology (Psy.D) in Clinical Psychology from the Chicago School of Professional Psychology at Westwood. Dr. Dicken’s work has been featured in GOOP, The Chalkboard Magazine, and in numerous other articles and podcasts. She is a licensed psychologist with the state of California.

Lena Dicken, Psy.D
Clinical Psychologist

A good question leaves room to talk about experiences. Good open-ended questions open the floor for someone to express their emotions and relay experiences. They help you find out someone's true feelings.
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How can you meditate on questions? Repeat the question and notice how it makes you feel and any initial reactions or answers. Is the question difficult to answer? Does it bring up challenging emotions? Meditating with a question simply means contemplating it. Acknowledge how the question makes you feel, then reflect on those feelings.^{[10]
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How do you have a thought-provoking conversation? Having a thought-provoking conversation can be as simple as “showing up” and listening. Engagement is key. The more present you are, the more connected you’ll feel in the conversation. Here are some tips for having a good conversation:^{[11]
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- Be present. Give the conversation your undivided attention—no distractions!
- Go with the flow. You never know where a conversation will lead, so don’t hesitate to jump from topic to topic.
- Ask open-ended questions. Avoid questions that can be answered with a simple “yes” or “no” answer.
- Be honest. If you’re unsure of an answer, don’t be afraid to admit it.
- Listen. Open your ears to what’s being said—you never know what you’ll learn.