350+ Deep Questions To Ask A Boyfriend, Girlfriend, Friends, Your Crush and more

Deep, compelling questions force us to think deeply, examine ourselves, and learn more about the people we want to get to know better. Trying to get to know someone, but not sure what the right questions to ask are? You’ve come a long way from small-talk and want to know if this is someone who could be a lasting friend or a potential romantic partner.

Or maybe you want to explore your own inner world through questions to move towards a new level of happiness, self-confidence and inner peace. Good deep questions are more personal questions that go beyond favorite colors and whether or not pineapple tastes good on pizza. Continue to read down below and choose from our list of deep questions the most meaningful one to ask someone special.

Deep questions to ask

We meet a lot of people in our daily life, without really being able to say that we know them well. Knowing someone’s routine, or even their personality, doesn’t mean you really know them. You often have to take the time to stop and talk to each other for more than five minutes to ask yourself the real questions. Use these deep questions and start to know someone better.

🔅What was your favorite subject or class in high school? 

🔅How do you relax when you’re stressed out? 

🔅What is your Achilles heel (your weak spot)? 

🔅What was the most memorable experience from your childhood? 

🔅If you could wake up tomorrow having gained any one quality or ability, what would it be? 

🔅What what the most intense experience you’ve had in your life? 

🔅If you were to die this evening with no opportunity to communicate with anyone, what would you most regret not having told someone? Why haven’t you told them yet? 

🔅Have you ever told a lie that you regretted? 

🔅Take four minutes and tell your partner your life story in as much detail as possible. 

🔅What is the most important lesson you’ve learned this year? 

🔅When you dream big, what would you do with your life? 

🔅How do you think you’d be different if you were raised in a different family? 

🔅When did you last cry in front of another person? By yourself? 

🔅Do you ever make excuses for your bad behavior? (e.g., I punched him because he was a jerk.). 

🔅What is your spirit animal? 

🔅What three non-electric or non-automatic items would you take on a deserted island? 

🔅Share a personal problem and ask your partner’s advice on how they might handle it. Also, ask your partner to reflect back to you how you seem to be feeling about the problem you have chosen.If you could have three wishes, what would they be? 

🔅Have you ever had your heart broken? What did it feel like to you? 

🔅What is a skill that you want to build? 

🔅Are you a mountain or a beach person? 

🔅Have you ever been camping? Did you like it? 

🔅What makes you feel nostalgic? 

🔅What do you want people to remember about you after you’re gone? 

🔅What was the most important lesson you’ve learned from a past relationship? 

🔅Share with your partner an embarrassing moment in your life. 

🔅What do you value most in a friendship? 

🔅What is your star sign? And do you believe in astrology? 

🔅What do you think of Elon Musk? 

🔅What is one accomplishment that you’re proud of? 

🔅Is there something that you’ve dreamed of doing for a long time? Why haven’t you done it? 

🔅If you had to eat only one meal for the rest of your life what would it be? 

🔅What are your passions in life? 

🔅Have you ever shoplifted anything? 

🔅Are you very close to anyone in your family? Why? 

🔅Do you believe in giving people second chances, and why? 

🔅If you redesigned society, what would you change? 

🔅What superpowers did you wish you had when you were a kid? 

🔅If you could change anything about the way you were raised, what would it be? 

🔅How would you describe your first crush? 

🔅Tell your partner something that you like about them [already]. 

🔅Have you ever done something you regretted? 

🔅What are your top three strengths? 

🔅Do you get deja vu? What does it feel like for you? 

🔅Do you have a secret hunch about how you will die? 

🔅Do you think psychics are actually psychic? 

🔅What’s one thing I don’t already know about you? 

🔅Your house, containing everything you own, catches fire. After saving your loved ones and pets, you have time to safely make a final dash to save any one item. What would it be? Why? 

🔅If you were going to become a close friend with your partner, please share what would be important for them to know. 

🔅What is your dream vacation? 

🔅Share something you consider to be a positive characteristic of your partner. Share a total of five items. 

🔅If you knew that in one year you would die suddenly, would you change anything about the way you are now living? Why? 

🔅Would you like to be famous? In what way? 

🔅Who was your favorite cartoon character when you were a kid? 

🔅What do you think the solution is to climate change? 

🔅Given the choice of anyone in the world, whom would you want as a dinner guest? 

🔅Do you believe in good and evil? 

🔅What does friendship mean to you? 

🔅If you could live anywhere in the world, where would you live? 

🔅What type of music energizes you? 

🔅Have you ever had an epiphany? If so what was it like for you? 

🔅If you could change one thing about your childhood what would it be and why? 

🔅What is your most terrible memory? 

🔅How close and warm is your family? Do you feel your childhood was happier than most other people’s? 

🔅If “hello” were to be replaced by another word as a greeting, what word would that be? 

🔅What roles do love and affection play in your life? 

🔅Are you still friends with anyone from high school? 

🔅Who is your doppelganger? 

🔅What are your top three positive qualities? 

🔅Tell your partner what you like about them; be very honest this time, saying things that you might not say to someone you’ve just met. 

🔅What is your place in the whole world? 

🔅What impresses you? 

🔅Make three true “we” statements each. For instance, “We are both in this room feeling… 

🔅For what in your life do you feel most grateful? 

🔅Do you think anyone has the capacity to cheat or do you think only cheaters cheat? 

🔅Are you a morning or a night person? 

🔅When you see your family, what do you do together? 

🔅How do you feel about your relationship with your mother? 

🔅What do you think of Steve Jobs? Hero or Villain? 

🔅If you could change one decision you made when you were younger what would it be and why? 

🔅What is the greatest accomplishment of your life? 

🔅What do you think makes a meaningful life? 

🔅Complete this sentence: “I wish I had someone with whom I could share… 

🔅Before making a telephone call, do you ever rehearse what you are going to say? Why? 

🔅What is your favorite workout? 

🔅What would be a perfect day for you? 

🔅What do you think of A.I. (Artificial Intelligence)? Scary or amazing? 

🔅What did you want to be when you grew up? 

🔅What do you think prevents people from manifesting their dreams? 

🔅What are your favorite hobbies? 

🔅Who or what inspires you? 

🔅Do you know how to play any musical instruments? 

🔅What is your favorite (least favorite) emotion? 

🔅What are some of your favorite books? 

🔅Name three things you and your partner appear to have in common. 

🔅What is your most treasured memory? 

🔅What, if anything, is too serious to be joked about? 

🔅What would constitute a “perfect” day for you? 

🔅If a crystal ball could tell you the truth about yourself, your life, the future, or anything else, what would you want to know? 

🔅What’s your least favorite food? 

🔅What does spirituality mean to you? 

🔅If you were able to live to the age of 90 and retain either the mind or body of a 30-year-old for the last 60 years of your life, which would you want? 

🔅When did you last sing to yourself? To someone else? 

🔅Of all the people in your family, whose death would you find most disturbing? Why? 

🔅Is there anything from the 1980s that you wish would come back? 

🔅What would you do if you found out you had a year to live? 

Deep questions to ask your boyfriend

Do you know each other so well that sometimes it seems to you that you have asked them all possible and imaginable questions, about their dreams, their fears and their past? This series of questions could well reveal to you facets of his personality that you did not know yet (and thus strengthen your love for him or her even more. If you don’t know what questions to ask your boyfriend read down below deep questions to ask your boyfriend.

🔔What do you do to get out of negative head spaces? 

🔔Who is that one person you’re comfortable discussing anything with? 

🔔What are you doing to improve the world? 

🔔If you could change one thing about me, what would it be? 

🔔Do I inspire you? 

🔔What is the one thing you would like to change about yourself? 

🔔Looking back, what is the one thing you wish you never did? 

🔔Why do you like spending time with me? 

🔔What is on your bucket list this year? 

🔔What is your best memory with someone you longer speak to? 

🔔What is the scariest thing that ever happened to you as a kid? 

🔔What is something you’re afraid to tell me? 

🔔What is the one thing or person you can lay down your life for? 

🔔What do you consider a waste of a life? 

🔔What are you most thankful for? 

🔔Were you nervous before our first kiss? 

🔔What are some of your rules that bend for no one? 

🔔What is your worst habit? 

🔔What is the biggest thing in your way? 

🔔How have I shaped your life? 

🔔What words hurt you the most to hear? 

🔔How many countries have you visited? 

🔔Do you think I would make a good parent? 

🔔When do you think a person is ready for marriage? 

🔔Would you move state/country for love? 

🔔What are your biggest goals in life, and what have you done to achieve them? 

🔔What is the best part about dating me? 

🔔If you could live in someone else’s body for a day, who would it be and why? 

🔔Have you ever lost someone close to you? 

🔔What is your biggest regret in life? 

🔔What is the one thing that people always misunderstand about you? 

🔔What do you believe happens to us when we die? 

🔔When was the last time you cried? 

🔔Do you ever feel nervous around me now? 

🔔When did you know you loved me? 

🔔What is the best bad decision you’ve ever made? 

🔔Are you afraid of failure? 

🔔What is unforgivable to you? 

🔔What are three events that have had the biggest impact on who you are today? 

🔔Have you ever been heartbroken? 

🔔What is one thing you want to achieve before you die? 

🔔Were you attracted to me right away? 

🔔What keeps you up at night? 

🔔What qualities do you admire about your parents? 

🔔If your relationship was taking a downturn, what would you do to save it? 

🔔What lesson have you learned the hard way? 

🔔What is the one thing that has kept you going during tough times? 

🔔Have you ever gotten back with an ex? 

🔔Do I have traits that are important to you in a relationship? 

🔔What is your biggest success? 

🔔How would you describe me in 3 words? 

🔔What values do you want your children to possess? 

🔔What qualities do you least admire about your parents? 

🔔What was your biggest passion as a child? 

🔔What is something you accomplished that you never thought you would? 

🔔What is one thing you’ve learned from me? 

🔔Do you usually stay friends with your exes? 

🔔Who is your best friend? 

🔔What qualities do you admire about me? 

🔔Do you believe in second chances? 

🔔What do you remember most about meeting me? 

🔔Do you consider yourself ambitious? 

🔔What has shaped your political beliefs? 

🔔Who is the most important person in your life right now outside your family? 

🔔What qualities do you admire about yourself? 

🔔What is your favorite memory with me?Who do you miss most in your life? 

🔔What is the biggest lie you’ve ever told? 

🔔Do other people’s opinions matter to you? 

🔔If you could live forever, would you want to? 

🔔What is the nicest thing I’ve ever done for you? 

🔔What is the most embarrassing thing that’s ever happened do you? 

🔔What has been your biggest mistake so far in life, and what did you learn from it? 

🔔What is the biggest lesson you’ve learned from our relationship? 

🔔When were you happiest in your life? 

🔔When were you the unhappiest in your life? 

🔔What makes a long-lasting relationship? 

🔔Do you think I’m the one? 

🔔Have you ever thought about ending our relationship? 

🔔What do you wish was better in our relationship? 

🔔What is the worst part about dating me? 

🔔Do you believe in karma? 

🔔What was your first impression of me? 

🔔What is the best birthday gift you’ve ever received? 

🔔What did you want to be when you were younger? 

Deep questions to ask a girl

🌞What or things or person has influenced you the most? 

🌞What’s your favorite photograph of yourself? 

🌞What is the most important thing a person can do to improve themselves? 

🌞What or who would you sacrifice your life for? 

🌞Do you think the future will be better than the present? Why? 

🌞Who do you think knows you the best? 

🌞Why are people so bad at judging risks? For example: people are terrified of murders, terrorists, and flying but they are much more likely to die driving to the store. 

🌞What makes a person truly evil? Are they born that way or did their environment make them that way? 

🌞If science makes it possible to predict which people will be more likely to commit crimes, should the highest risk individuals be jailed or killed before they can commit crimes? 

🌞Why does society place such a high value on beauty when it serves no functional purpose? 

🌞Would you like to be famous, if so, in what way? 

🌞What’s the best present or gift you’ve ever received from someone? 

🌞What’s your most terrible memory that you’d love to forget about? 

🌞What is your greatest accomplishment? 

🌞Do you think that war is inevitable or can it be ended completely? 

🌞What role models do you respect the most? 

🌞What much is a human life worth and are some lives worth more than others? 

🌞Would you rather live in a small house with an amazing view, or a massive mansion in a subdivision? 

🌞Can you speak in any foreign languages? If yes, can you show me? 

🌞How do you spend your free time, and where do you like to go? 

🌞What are some examples of outside behaviors that are symptoms of inner emotional scars? 

🌞What’s your dream career? 

🌞Will humans spread out among the stars or just be a brief blip in Earth’s history? 

🌞If tomorrow you woke up with a new quality, talent or ability, what would you like it to be? 

🌞In four minutes, tell me your life’s story. 

🌞If you could live anywhere in the world, where would it be? 

🌞What is one thing you were afraid to do but felt amazing after you accomplished it? 

🌞If you could have dinner with anyone in the world, past or present, who would you choose? 

🌞If your house caught on fire, what would be one thing you would have to save first? 

🌞Do you think the present is better than 50 years ago? Why? 

🌞What skill would you like to become a master at? 

🌞What do a lot of parents do that screws up their kid? 

🌞Are there any places you would love to travel to? 

🌞What is your favorite and most treasured memory? 

🌞What about yourself, do you find the most pride in? 

🌞What’s the most extreme example of poverty you have seen? 

🌞What’s your favorite place in the world? 

🌞Do you think human morality is learned or innate? 

🌞Is there any way for governments to avoid power corrupting its politicians? If so, how? If not, what part of human nature makes corruption unavoidable? 

🌞If you could play the role in any movie, what person would you want to be? 

🌞Why are there so many people who are lonely? Why is it so hard for people to make real connections when almost everyone wants to make real connections? 

🌞What’s one thing on your bucket list? 

🌞What keeps you up at night? 

🌞Why have apocalyptic games, movies, shows, and books become so popular in the past few years? What does it say about our culture or society? 

🌞Do you think that humans as a species have gotten better through the generations or worse? Why? 

🌞If you had unlimited money, what would you do with it? 

🌞What lies do you most often tell yourself? 

🌞What’s the most crucial thing for a healthy relationship? 

🌞What’s one thing you’ve learned that most people don’t know how to do? 

🌞What’s one thing you’ve done, but will never end up doing again? 

🌞What single event has had the biggest impact on who you are? 

🌞What are the most common road blocks that stop people from achieving their dreams? 

🌞What are some examples of small changes that can be made that really improve the lives of a country’s citizens? 

Deep questions to ask your girlfriend

The key to any long-term relationship is getting to know the person you’re dating. It is therefore important to choose the best questions to ask your girlfriend in order to find out as much as possible about her. To get to know better your girlfriend you need to ask the right questions. Read down below and choose the best deep questions to ask your girlfriend. These questions will help you to know your girlfriend on a deeper level.

🤩What is one thing about me that surprised you?

🤩How did you know you wanted to be in a relationship with me?

🤩What are you most proud of in your life?

🤩What is one part of yourself that you think still needs work?

🤩What is the meaning of life?

🤩Do I ever make you unhappy?

🤩What is your greatest fear?

🤩Hard and fast, or slow and sensual?

🤩What do you admire most about me?

🤩How do you measure success?

🤩What was an aspiration you had when you were younger that you no longer want to achieve?

🤩What scares you about becoming a parent?

🤩Do you love yourself?

🤩Would you rather be with someone with no sexual experience or a ton of sexual experience?

🤩What was the hardest thing that you ever had to get through as a kid?

🤩Do you feel like money affected the way you grew up? How so?

🤩Have you ever felt like giving up in the past?

🤩What is one thing you think makes our relationship unique from everyone else’s?

🤩When did you last cry in front of another person?

🤩How do you feel about your gender?

🤩What’s something unexpected that turns you on?

🤩What do you fantasize about when you masturbate?

🤩Which part of your body do you want me to touch more?

🤩What’s a sex position that you’ve never tried that you’re curious about?

🤩What would you change about me if you could?

🤩In what ways do you think you have grown as a person?

🤩How often do you masturbate?

🤩What is your favorite activity to do with me?

🤩Morning sex or evening sex?

🤩What is an innocent mistake you made that had dramatic consequences?

🤩When do you feel most alive?

🤩What is the most difficult thing you’ve ever had to go through?

🤩Would you rather have average sex every day or amazing sex once a month?

🤩What is something you failed badly at?

🤩What does commitment mean to you?

🤩Was my first impression of you a good one or a bad one?

🤩What do you think you would be like as a mother?

🤩Are you close with your family?

🤩What is your relationship with your parents like?

🤩What do you think your younger self would think about who you are today?

🤩Do you think humans are inherently good or inherently evil?

🤩Do you think our society is progressing or regressing these days?Lights on or lights off?

🤩What was your hottest sexual experience (before meeting me)?

🤩Do you feel like race has affected your life? How so?

🤩Would you ever have sex in a public place?

🤩Do you have any kinks, fetishes, or guilty pleasures?

🤩What do you think was your most vulnerable moment in our relationship?

🤩Where is your favorite place to be with me?

🤩If you could change one thing about me and the way I treat you, what would you change?

🤩Has it always been that way?

🤩Do you think you are misunderstood?

🤩Dominant or submissive?

🤩Do you want to change anything in me?

🤩Is there someone you haven’t spoken to in a long time that you miss?

🤩Would you be interested in watching porn with me?

🤩What do you do when heartbroken?

🤩When is the last time you felt truly, exuberantly happy?

🤩Have you ever loved someone who didn’t love you back?

🤩Would you change anything about the way you grew up?

🤩What did you learn from your last relationship?

🤩Do you like porn?

🤩Do you think your family knows the real you?

🤩What do you think is your biggest strength in this relationship?

🤩Would your younger self be proud of what you’ve achieved so far?

🤩What is the most courageous thing you have ever done?

🤩Do you find it hard to trust people?

🤩Which do you enjoy more: oral or penetration?

🤩If our relationship ended, what is the one thing about it you would miss the most?

🤩When was the first time you looked and me and realized that you were in love with me?

🤩Looking back on your life, what have you done that has given you the most satisfaction?

🤩What are you most attracted to about me?

🤩Is there anything from your past that you’re ashamed about?

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

🤩If money wasn’t an issue, how would you spend your days?

🤩What’s your favorite part about my body?

🤩What do you think about the concept of marriage?

🤩Is there ever a good excuse to tell a lie?

🤩What is your biggest passion?

🤩Do you think I have an irrational fear of something?

🤩What does an ideal relationship look like to you?

🤩What do you look for in a relationship?

🤩What feels hard in your life right now?

🤩What is one thing you want to accomplish together by this time next year?

🤩What scares you most about our relationship?

🤩What is your favorite physical feature of mine?

🤩Do you want to spend the rest of your life with me?

🤩If you could hook up with any celebrity in the world, who would you pick?

🤩What is one thing about your parents’ relationship that you seek to emulate?

🤩Are relationships meant to last forever?

🤩What is the nicest thing I have ever said to you?

🤩Why do you think you are the way you are in relationships?

🤩What is one secret you’ve wanted to tell me, but haven’t?

🤩Has anyone ever broken your trust beyond repair?

🤩What are the values you hold dearest to you?

🤩What are you most ashamed of?

🤩Do I make you feel good about yourself?

🤩What’s your favorite sex position?

🤩What was your childhood like?

🤩How do you like to be kissed?

🤩Do you think we could parent well together if we had children?

🤩Do you like the idea of getting tied up (or tying me up)?

🤩What is one thing I do for you that you are truly grateful for?

🤩Who do you want our children to take after?

Deep questions to ask a guy

🧐What is your definition of love?

🧐What is your biggest goal in life?

🧐What is one thing you appreciate the most?

🧐Do you believe everything happens for a reason?

🧐Are you a religious or spiritual person?

🧐Have you ever had your heart broken?

🧐What makes you feel alive?

🧐Do you think men and women can ever really be friends?

🧐Do you feel fulfilled by your job?

🧐What is one behavior you never tolerate?

🧐What song speaks to your soul?

🧐What does your perfect day look like?

🧐What is one thing you can never forgive?

🧐Who can you talk to about anything?

🧐How much control do we have over our lives?

🧐Do you think technology is destroying us or enhancing our lives?

🧐What quote or mantra do you tell yourself most often?

🧐What do people thank you for most often?

🧐Do you have any recurring dreams?

🧐Do you get overwhelmed easily?

🧐Do you believe in heaven?

🧐Have you ever questioned your sanity?

🧐Do you believe in aliens?

🧐What is one thing you take for granted?

🧐What is the best compliment you’ve ever received?

🧐What do you think keeps people in toxic relationships?

🧐What’s the best way to end a long day?

🧐What is your proudest accomplishment?

🧐Are you an introvert or extrovert?

🧐What is your weirdest habit?

🧐Do you have any phobias?

🧐What always makes you cry?

🧐Where does true happiness come from?

🧐What has been your favorite age so far?

🧐Do you believe in destiny?

🧐What’s one thing you always procrastinate on?

🧐After you die, what would you like to be remembered for?

🧐Do you think people can really change?

🧐What kind of parent do you think you’ll be?

🧐Do you believe in karma?

🧐In what ways are you stronger than you look?

🧐If you could live the rest of your life and never feel pain, would you?

🧐What is the biggest sin our of the 7 deadly sins (pride, greed, lust, envy, gluttony, wrath, sloth)?

🧐Have you ever been in trouble with the law?

🧐Have you ever lost someone close to you?

🧐What should a healthy relationship provide for the people in it?

🧐Do you believe in the afterlife?

🧐What do you think we’re doing here?

🧐What would you do differently if you got the chance to relive the past 5 years?

🧐Do you believe we all have a soul or are we just a series of electrons and neurotransmitters?

🧐What are you most insecure about?

🧐What was the happiest period of your life?

🧐How has your sense of right and wrong evolved?

🧐What is one thing you’re happy you’ll never have to do again?

🧐What’s one mistake you will never make again?

🧐What was your biggest ‘what was I thinking’ moment?

🧐What could the government do to actually improve everyone’s lives?

🧐What always makes you angry?

🧐What is the biggest lie people tell themselves?

🧐How would your closest friends describe you?

🧐What is one thing no one realizes about you?

🧐What lesson do you wish you learned earlier in life?

🧐If you woke up tomorrow with no fear, what would you do first?

🧐What is one bad habit we are all better off without?

🧐Which aspect of your life is going really well right now, and which area could use some help?

🧐What is always worth the wait?

🧐What do you wish you could remember more clearly?

🧐What 3 qualities do you admire most in another person?

🧐Do you think we will ever have a definitive answer for what is the meaning of life?

🧐Do you think all diseases will be cured someday?

🧐Do you believe in reincarnation?

Deep questions to ask friends

The best way to get to know a person is also (perhaps) the simplest: ask him about things. When a friendship is born, in fact, in addition to (re) knowing each other in a natural and instinctive way, the most effective way to discover the affinities (or not) with the other is to ask the (right) questions. We have the right questions for you right down below. Choose from down below the right deep questions to ask friends and make your friendship even stronger.