One of the best ways to get to know someone is by asking them questions, but in order to start deep, meaningful conversations you need to be asking the right questions.
It’s easy to get stuck having surface level conversation, which is why we put together the following deep questions to help you connect deeply.
These deep questions to ask your friends and family are the perfect conversation starters to use when you want to get to know someone on a more personal level.
Sections
- Deep questions to get to know someone
- Deep questions to ask a girl you like
- Deep questions to ask a guy you like
- Questions for couples
- Question games
- Deep questions to ask your friends
- Deep questions to ask your best friend
- Deep questions about life
- Deep questions about love
- Deep personal questions
- Funny, but also deep questions
Deep questions to get to know someone
These deep questions are helpful to get past surface level small talk and get to know someone on a deeper level. They should be used when you’ve already spent some time getting to know someone. Because this is someone that you don’t already have a deep connection with controversial topics should be avoided, but that doesn’t mean that you can’t ask them more personal questions to get to know them better. Suitable situations would be wanting to get to know a colleague better or turning an acquaintance into a closer friend.
1. Is there anything from your past that you regret?
 
2. Do you know what your life purpose is?
 
3. What is the happiest memory that you have?
4. What is your worst fear?
 
5. Do you want to fall in love?
 
6. What is the most important lesson you learned in your last relationship?
7. Are you more of an introvert or an extrovert?
 
8. Is your glass half full or half empty?
 
9. What in life are you most passionate about?
10. Who or what inspires you?
 
11. What’s your greatest strength?
 
12. How important is family to you?
13. Do you believe that each of us has a soulmate?
 
14. What is a quality that your parents tried to teach you but you feel you didn’t learn?
 
15. Do you think there is an age where people should be settling down?
16. Do you believe in a higher power? If yes, have you ever prayed to them?
Deep questions to ask a girl you like
When you start talking to a new girl that you like it is important to strike a balance between questions that are flirty and meaningful. Asking these deep questions to start a conversation with a girl you like is a great way to get to know your crush. These conversation topics are good to use both over text and in person and are appropriate to use on a second date or after you’ve spent some time texting with them.
1. What is your love language?
 
2. What does your perfect date look like?
 
3. What is your dream job?
4. How would your friends describe you?
 
5. What is the most important thing you look for in a partner?
 
6. What in your life do you feel most proud of?
7. Where do you see yourself in five years?
 
8. Is there something you think a lot of parents do that negatively impacts their kids?
 
9. What makes you smile when you’re having a bad day?
10. What in your life do you feel the most grateful for?
 
11. Can you remember the last time you cried and what the reason was?
 
12. Who in your family do you feel the closest to?
13. How important is intimacy to you in your relationships?
 
14. What keeps you up at night?
 
15. Is self-improvement important to you?
Here is a list of other questions to ask a girl if you like her.
Deep questions to ask a guy you like
These questions were created for you to use to get to know your crush better and really understand his character. There is nothing wrong with being a little fun and flirty, but it’s also important to steer the conversation so that you get to know him on a deeper level. They are perfect to use over dinner, or over text to keep the conversation more interesting without being too serious. These questions are on the deep side, and for this reason, they are more suitable for a second date or after you’ve been texting for a while.
1. Do you know what your attachment type is?
 
2. Are you looking for something serious or casual?
 
3. Would you rather spend a night cozy at home or out at the club?
4. Are you close with your parents?
 
5. Do you have a good work-life balance?
 
6. What’s your favorite childhood memory?
7. What is more important to you, love or money?
 
8. Why did your last relationship end?
 
9. What is your relationship like with your father?
10. Are you able to fight in a loving way?
 
11. What are some qualities that you wish you had?
 
12. Have you ever stayed in a relationship that you knew was toxic? If yes, why?
14. Are you aware of the ways that you self-sabotage?
 
15. How important is your health to you?
 
16. If you’re having a hard day, how can I show up for you to make it better?
Questions for couples
It doesn’t matter if you’re a married couple or have only been dating for a couple months, there is always more to learn about the person you’re with. If you feel stuck on not knowing what the best relationship questions that will allow you to connect with your partner in a meaningful way are, then these conversation starters are perfect for you. These are deep personal questions that will allow you to get to know your partner better, and give you great insight into the ways that you can make them feel more loved. They can also be helpful to improve communication in a relationship.
Deep questions to ask your boyfriend
Here is a list of deep questions to ask your boyfriend in order to better understand him, and strengthen the quality of your relationship.
1. If you had a big decision to make, would you talk to me or your mom first?
 
2. Have you ever cheated on anyone?
 
3. Who was your role model growing up?
4. Do you know what your attachment type is? (If you don’t know yours, it’s worth looking into)
 
5. What’s the best way to cheer you up on a bad day?
 
6. Do you think it’s possible for men and women to just be friends?
7. If you could trade places with someone for the day, who would you choose?
 
8. What is one thing you wish you could change about yourself?
 
9. Is there anyone you feel jealous of?
10. What was the most difficult time of your life?
 
11. What was the best time of your life?
 
12. Is it ever okay to lie?
13. What is more important in a relationship: a physical or emotional connection?
 
14. What’s the biggest sacrifice you’ve made for your partner?
 
15. What is your greatest fear in a relationship?
Deep questions to ask your girlfriend
By asking the following deep questions for your girlfriend you can better understand her needs in your relationship, and deepen the connection that the two of you share.
1. When you have a problem do you want me to help you find a solution or just comfort you?
 
2. Is foreplay important for you to feel comfortable during sex?
 
3. How can I make you feel supported when you have a bad day?
4. In what way do you mostly easily receive love?
 
5. What is the best advice someone has ever given you?
 
6. Do you have any relationship deal-breakers?
7. What do you consider cheating? (porn, onlyfans, flirting)
 
8. If you had to go back to school, what would you study?
 
9. What do you like most about yourself?
10. What’s one thing I can do to make our relationship better?
 
11. Do you feel like we communicate well?
 
12. Is there any way we can support each other better?
13. What is your worst fear?
 
14. How do you know when you’re in love?
 
15. What do you fantasize about?
16. What inspires you?
 
17. What challenging life experiences have made you stronger?
 
18. When are you happiest?
19. What does your perfect relationship look like?
 
20. Do you feel more loved when I compliment you or cuddle you?
Deep questions and conversation starters for couples
Continuing to learn more about your partner throughout your relationship is important if you want to keep your connection deep and interesting. Use these conversation topics during your next date night and enjoy creating a deeper and more meaningful connection with your partner.
1. Do you love what you do enough to want to do it for the rest of your life?
 
2. What has been the happiest day of our marriage?
 
3. What is one thing you feel I’ve really helped you with throughout our relationship?
4. Do you feel as though I support you well?
 
5. Is there anything I could do to make you feel more supported?
 
6. What would a perfect day spent together look like/
7. Do you feel as though the tough times in our relationship have brought us closer together?
 
8. What are your biggest fears in our relationship?
 
9. What is one thing you think I could work on?
10. Is there anything new that you want to try in bed?
 
11. What is one way that I could try to be more understanding?
 
12. Where do you see us in five years from now?
13. Are there any things that we don’t do together any more that you miss?
 
14. Do you feel as though you have enough intimacy with me?
 
15. Do you feel safe in our connection?
16. Is there anything I could do to make you feel more loved?
Question games
When you’re out with friends sometimes it can feel hard to keep the conversation flowing naturally and make sure that no one at the table is feeling left out. Playing games can be a really good way to keep everyone’s attention, and it’s also a great way to get to know your friends a little better. These questions can be a little on the controversial side, but in this situation that’s okay. With the right questions you can use these games to get past surface-level conversation and really get to know your friends in a fun way.
Here are a few lists of some fun questions to ask during your next game night.
Deep would you rather questions
Playing would you rather is a great way to get to know random and interesting facts about your friends. Here is a list of deep questions to ask during a game.
1. Would you rather marry someone who is rich that you can’t stand, or that you love but you’ll always be poor?
 
2. Would you rather live in the same place for the rest of your life, or have to move to a new country once a month for the next 5 years?
 
3. Would you rather be an expert at only 1 thing or average at a lot of things?
4. Would you rather have 10 kids or no kids at all?
 
5. Would you rather time-travel 10 years into the future or 100 years into the past?
 
6. Would you rather live forever or die tomorrow?
7. Would you rather be beautiful and dumb or unattractive and intelligent?
 
8. Would you rather lose your hearing or vision?
 
9. Would you rather be able to speak any language fluently or speak with animals?
10. Would you rather live in a big city or the middle of nowhere for the rest of your life?
 
11. Would you rather be the funniest or smartest person in a room?
 
12. Would you rather find your soulmate or your life purpose?
13. Would you rather work out every day for the rest of your life or never work out again?
 
14. Would you rather confess to cheating on your partner or catch your partner cheating on you?
 
15. Would you rather be too trusting of everyone or trust no one?
16. Would you rather work a job you love and be poor or work a job that you hate and be rich?
 
17. Would you rather lose everything you own in a fire or lose a loved one?
 
18. Would you rather be criticized or ignored?
19. Would you rather have your boss or your parents look through the photos on your phone?
You can find more ideas to try in this complete list of would you rather questions.
Deep truth or dare questions
Are you ready to stir the pot during “Truth or dare”? Here are some deep truth-or-dare questions to ask your friends.
1. What’s your biggest insecurity?
 
2. What’s your biggest regret?
 
3. What’s one thing you would do if you knew there wouldn’t be any consequences?
4. When was the last time you got rejected?
 
6. What was the thing that ruined your last relationship?
 
7. What’s your worst habit
8. Have you ever been caught doing something you shouldn’t have been? If so, what was it?
 
9. Do you believe in any superstitions? If yes, which ones?
 
10. What’s your most embarrassing childhood memory?
11. Have you ever considered cheating on your partner?
 
12. What’s something you’ve done that you still feel guilty about to this day?
 
13. What’s the last lie you told?
14. What is the biggest misconception people have about you?
Deep never have I ever questions
“Never have I ever” is a great way to see which of your friends are living life on the edge. Get to know your friends on a deeper level while still having fun with them by asking these questions.
1. Never have I ever broken a bone
 
2. Never have I ever skipped work or school
 
3. Never have I ever been broken up with by a partner
4. Never have I ever gone into overdraft on my bank account
 
5. Never have I ever kissed someone of the same sex
 
6. Never have I ever tried psychedelics
7. Never have I ever read through my partner’s texts
 
8. Never have I ever been a bride’s maid or best man
 
9. Never have I ever been in a fight
10. Never have I ever had a one-night-stand
 
11. Never have I ever lied to my best friend
 
12. Never have I ever been fired from a job
13. Never have I ever held a grudge for over a year
 
14. Never have I ever given or received a lap dance
 
15. Never have I ever gone on vacation by myself
16. Never have I ever stolen something
 
17. Never have I ever fallen in love
 
18. Never have I ever moved to a new city
19. Never have I ever been in a car crash
Deep this or that questions
“This or that” is a simple game that is perfect to play when you feel nervous meeting a new group of friends and need an easy way to break the ice. These questions will allow you to form deeper connections while still keeping conversation light.
1. Movies or books?
 
2. Work hard or play hard?
 
3. Intelligent or funny?
4. Money or free time?
 
5. Honesty or white lies?
 
6. Life or death?
7. Love or money?
 
8. Sad or mad?
 
9. Rich partner or loyal partner?
10. Money or freedom?
 
11. Friends or family?
 
12. Night out or night in?
13. Spend or save?
Deep questions to ask your friends
These deep and personal questions for friends definitely aren’t suitable to be used with strangers, but are perfect to ask your close friends to better understand their past as well as their dreams for the future. There are very few feelings that are better than feeling seen and deeply understood by someone, so asking these meaningful questions and really paying attention to the answers is a great way to strengthen your bond with your close friends.
1. When you look into the past, what do you miss the most?
 
2. What is the most spontaneous thing you’ve ever done?
 
3. Do you think that good things come from suffering?
4. What are three qualities that you look for in friends?
 
5. Are there any lessons that you had to learn the hard way?
 
6. What is the best part about being you?
7. Is there anyone that you really miss right now?
 
8. What was the hardest day of your life?
 
9. When you’re having bad days what do you do to cheer yourself up?
10. Do you prefer having a lot of good friends, or a few great friends?
 
11. What is the weirdest quality you have?
 
12. Where do you see yourself one year from now?
13. What has the fear of failure stopped you from doing?
 
14. On a scale from 1-10 how would you rate this last week?
 
15. What is one thing about yourself you’re working to improve right now?
16. Is there anything that you want more of in your life right now?
 
17. What do you think is your greatest strength?
 
18. What makes you feel safe?
Go here if you want more deep questions to ask your friends.
Deep questions to ask your best friend
In order to strengthen your friendship it’s important to continue asking meaningful and deep questions, and put effort into better understanding your best friend. When you’ve been friends with someone for a long time it can feel hard to think of deep conversation topics that haven’t already been covered, but this is a great list to use to deepen your conversation. Some of these questions are quite serious and may feel vulnerable for both of you to talk about, so make sure to ask them in a safe space, and be ready for some deep emotions to come up.
1. Do you think it’s possible to learn lessons without making mistakes first?
 
2. With that answer in mind, do you think you should change how you treat yourself when you make a mistake?
 
3. What is your favorite memory with me?
4. Is there anything I could do to make you feel more supported in our relationship?
 
5. What was an experience where you felt let down by me recently?
 
6. What qualities make a person beautiful?
7. Are there any wounds from your childhood that you feel still affect you today?
 
8. Is there anything I can do to help you heal them?
 
9. What is one weakness that I have that you think I could work on?
10. What do you admire most about me?
 
11. What do you admire most about yourself?
 
12. What have you read online recently that inspired you?
13. If you could live one day of your life on repeat forever, what day would it be?
 
14. If you were to spend a day spoiling yourself, what would you do?
 
15. When you think about ‘home’, what comes to mind?
16. Would you trust me with your life?
 
17. Is there a time in your life when you worked harder than ever before, but loved every minute of it?
 
18. What’s your favorite way to show somebody love?
19. What is a big step that you need to take, but are afraid to?
 
20. Who is your idol?
Deep questions about life
These deep conversation starters have a broad range of subjects for you to choose from. They are suitable for most of your more personal relationships but aren’t appropriate to ask most strangers. They will help you to better understand how your friends and family view life and death, and the world as a whole.
1. What life lesson have you learned the hard way?
 
2. Is there anyone that you compare yourself to?
 
3. What is your happiest childhood memory?
4. What is something that you wish you started working on 5 years ago?
 
5. What was the hardest day of your life?
 
6. How old do you feel like you are?
7. If you knew you were going to die tomorrow, how would you spend today?
 
8. What do you think is the meaning of life?
 
9. What’s one thing you’d be doing right now if you weren’t afraid of being judged?
10. Do you think there is a difference between living and existing?
 
11. What does your dream life look like?
 
12. If you had a friend that spoke to you the same way you spoke to yourself, would you be friends with them?
13. What makes you feel like life is worth living?
 
14. Are you holding onto anything that you need to let go of?
 
15. How good are you at following your heart?
16. When you’re on your deathbed do you think there’s anything in your life that you will regret?
 
17. What is worse, failing or never trying?
Deep questions about love
The topic of love is one that can stir up a lot of emotions, but can also open you up to have conversations that are less intellectual and more full of heart. Talking about love with the people close to you can allow you to really understand their past, the way that their experiences have shaped how they see the world, and to connect with them in a more meaningful way than you may be used to. These questions are better to be used in person than over text, and are best to be used with people that you know well.
1. Do you believe in soul mates?
 
2. If yes, do you think that you’ve met yours yet?
 
3. Do you think it’s possible to have a happy marriage?
4. How old were you the first time you fell in love?
 
5. Who was the first person to break your heart?
 
6. Are you afraid of love?
7. Do you believe in love at first sight?
 
8. Do you want to get married?
 
9. Who are your role models for love?
10. Is your heart open or closed?
 
11. Do you think that loving is something you get better at with practice?
 
12. What does love mean to you?
13. What about a person makes you fall in love with them?
 
14. Who in your life was it the most difficult to say goodbye to?
 
15. Who do you love and what are you doing about it?
16. What makes you feel the most loved by someone?
 
17. Do you think that love has a feeling?
 
18. If so, what does it feel like?
19. If you could meet the love of your life tomorrow, would you want to?
 
20. Do you feel like there is always one person who is more in love in a romantic connection?
Deep personal questions
The following deep and personal questions are great conversation starters for friends that you have an established relationship with and want to get past surface level conversation with. These are personal questions that will allow you to learn important details about how your close friends really feel about their lives and the world around them. You could even use them at a family dinner to connect more intimately with the members of your family.
1. Who or what do you think of when you think about love?
 
2. What is the loneliest moment of your life?
 
3. What in your life do you feel the most grateful for?
4. What is a life lesson that you learned recently?
 
5. What’s something that you can’t live without?
 
6. Is it more important to you to love or be loved?
7. What is something you would do if you knew you couldn’t fail at it?
 
8. Is there anyone close to you that you wish you had a better relationship with?
 
9. What gives your life meaning?
10. When was the last time you cried, and why?
 
11. Do you think it’s possible to be perfect?
 
12. What is one trait about yourself that you absolutely love?
13. What is a limiting belief that comes up when you feel challenged?
 
14. What is a quality that you have that you try not to let others see?
 
15. Do you think it is better to be loved or feared?
16. What is the greatest challenge you’re facing in your life right now?
 
17. Is there any way I can support you in overcoming that challenge?
 
18. What are three words you would use to describe the last 3 months of your life?
19. What is one thing that you would tell yourself 5 years ago?
 
20. If the goal of working was to be happy, not rich, would you change occupations?
 
21. What’s something about your mom that really irritates you?
Funny, but also deep questions
There are of course times where lighthearted conversation topics are preferred, and these are the perfect questions to use in such occasions. These funny, but deep questions are the perfect balance of meaningful and fun and can allow you to learn interesting facts about your friends, while also being less on the serious side. They are suitable for in person conversation and can also easily be used over text.
1. If I was an animal, what do you think I would be?
 
2. What’s the most embarrassing thing you’ve done recently?
 
3. If you were invisible for a day, what would you do?
4. How do you think you’re going to act when you’re 80?
 
5. Is there something that you think is impossible to look good while doing?
 
6. What song will you be playing for your kids in 20 years that will make you seem really old?
7. What’s the weirdest tinder profile you’ve ever seen?
 
8. What’s something that you always feel embarrassed buying?
 
9. If your life was a movie, what would it be called?
10. Would you date the opposite gender version of yourself?
 
11. If your parents got a call to bail you out of jail, what would they think you got arrested for?
 
12. Do you think there is any way that we’re actually living in the Matrix?
13. If you got kidnapped, what would you do that would be so annoying that it would make your kidnappers return you?
 
14. If you had to lose one body part what would it be?
 
15. What Disney character are you the most similar to?
16. On a scale from 1-10 how basic do you think you are?
 
17. What’s the weirdest place you’ve ever fallen asleep?
 
18. If you had to wear one outfit for the rest of your life, what would it be?
Questions to ask if really he wants to spend his life with you