Deep questions to ask family

Deep questions to ask family DEFAULT

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Deep questions to ask are compelling. And they're all in this post.

Whether it's a dinner date or you want to get to know someone, we have all the best questions to ask. Personal questions and powerful questions are all the expertise we have.

Be prepared for a meaningful conversation through the heart, soul, and mind one hard question at a time. Let's go into deeper territories.


The Best Deep Conversation Topics

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Okay, now that you have a good idea of approaching these questions, let's go over a few deep conversation topics.

These aren't questions. They're general ideas to keep on the back burner. Our questions are perfect when you're stuck. These conversation topics can be molded to fit your exact situation. After all, there's no predicting where an interesting conversation may go.

Take these topics, and use them to form your own unique and more profound questions catered directly to your company.

Here are some of the best deep conversation topics:



Goals and Aspirations








The Universe

Significant Events

The Future/Past





8 Best Deep Conversation Starters

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These deep conversation starters act as starting points. Many of them are open-ended and can lead virtually anywhere.

Remember: conversation starters give you a topic to work with. It's up to you to keep the conversation flowing.

So, what are some deep questions that would stimulate your mind and indeed give you something to begin with?

Here are 8 of the best deep conversation starters:

1. Would you rather live 120 years comfortable but dull, or live half as long but have an exciting adventure-packed life?

What's better – a long life or a well-lived one? This conversation starter can lead to inspiring conversations. Plan an adventure now!

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2. Would you sacrifice yourself for a stranger?

How much value do you put on human life as a whole? What if the stranger was a child? Would it depend on the circumstances given, or would they say yes no matter the situation?

3. What's the most memorable lesson you learned from your parents?

What's that lesson that has stuck with you all these years? This is an excellent opportunity for you to learn a thing or two, so pay attention to the answer.

4. How have your priorities changed over time?

Yesterday's dreams aren't always today's reality. What drives you now, compared to last year or even ten or twenty years ago.

5. What memory instantly makes you smile?

This question immediately adds comforting warmness to the conversation. It can also help you to make new memories along the same lines.

6. Do you think pet peeves reflect something about a person?

They say what we think of as our biggest pet peeve, and the worst thing in the world can tell a lot about us as an individual. It's random questions like this that make you think.

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7. What movie has made you into a better person?

There's always that one movie that made us want to have a better life.

8. If a genie granted you 3 wishes right now, what would you wish for?

Don't say you don't have a prepared answer for this profound but fun question!

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10 Best Deep Questions to Ask

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Quite simply, these are some of our best deep questions. They're the ones that really cut to the core and open up the lines of communication. They're the questions that lead to conversations that you remember long after they're over. Use them wisely.

Here are 10 of the best deep questions to ask:

9. What is your biggest regret in life?

This interesting question makes great conversation. This gives you a deeper connection and knowledge with who you're talking to.

10. What is the craziest thing you have done as a kid?

This sometimes presents itself as those casual questions that we can all laugh about.

11. What is your happiest memory with a loved one?

True love goes deeper than a romantic relationship. They say that memories are love's greatest preservatives. This is a great question because you get to reminisce meaningful memories. Everyone loves looking back at happy memories.

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12. What is your dream job?

And how close or far are they to it?

13. What do you think are the 5 most beautiful things in the world? Why?

Beauty is in the eye of the beholder. It takes on different meanings for different people. This question can help you to gain a new perspective.

14. What makes you feel most empowered?

Whether it's lifting weights or blocking someone on Facebook, there are moments when we feel on top of the world.

15. Which is more important: what you say or how you say it?

Words can take on different meanings depending on the context, inflection, facial expressions, body language, and countless other factors. Is the content what matters, or how the content is portrayed?

16. Do you believe in heaven and hell?

When thinking of what are some deep questions to ask, sometimes it is better to be straight to the point. Why or why not?

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17. Would you consider yourself an introvert or an extrovert?

The answer to this question says a lot about how people view themselves.

18. What is your guilty pleasure?

It's a good conversation if the other person decides they're okay with opening it up to you!

10 Best Deep Questions to Ask a Girl

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Whether you're dating or chilling with a platonic friend, these deep questions to ask a girl will help you connect with her in a way that lasts.

As a guy, forming an authentic relationship with a girl can be tricky. Having heartfelt questions to ask a girl shows that you genuinely care about her beyond a superficial level. It proves that you value what's inside.

Here are 10 of the best deep questions to ask a girl:

19. What's your greatest accomplishment so far?

Learn about what makes her proud. Be sure to ask follow-up questions about the work she put in to get there.

20. What’s your favorite thing about yourself?

This question helps you understand her best traits while also letting her brag a bit. It opens up plenty of opportunities for you to compliment her, too. Always take an opportunity like this.

21. What impression do you think you give when you first meet someone?

It's tough to know how you come off to new people. This question can help both of you to learn about yourselves and each other.

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22. What is your idea of a healthy relationship?

There's no need to ask a relationship expert for this. Sometimes, we get insightful answers from a past relationship.

23. What is your idea of a perfect day?

Maybe you can help them achieve that perfect day.

24. Do you believe in love at first sight?

Whether they do or don't, you'll get to know them on a deeper level.

25. What gets you in a bad mood?

It's better to understand it early on, so you avoid doing it to them. We all have different reasons for our bad moods, and they're all valid.

26. Do you believe in second chances?

And if they don't, would they be okay with not getting a second chance?

Couple having a romantic moment together

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27. What is a relationship deal-breaker for you?

We all have that one thing that just ruins everything, no matter how perfect the other person might seem.

28. How would you describe your last relationship?

Sometimes, challenging them to describe it in just a word makes the question a more fun conversation topic.

10 Best Deep Questions to Ask a Guy

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While these questions to ask a guy may not be ideal for your bar buddies (unless you've had quite a few), they're perfect for bonding with your close friends.

Your guy friends are family. In fact, sometimes they fill an essential role that your blood family can't. When you really need someone to talk to, you can count on your best friends to lend an ear.

These questions can help you to get to know a new friend a little better. They can also be used to spark a discussion with your tight friends when you just feel like making a connection with someone.

Here are 10 of the best deep questions to ask a guy:

29. When was the last time you really pushed yourself to your physical limits?

Whether it was a good day at the gym or a hike up a mountain, physical exertion usually comes with an exciting story.

30. When in your life have you been humbled?

Whether it's witnessing a professional athlete or learning from a mentor, there are moments when we recognize our shortcomings, and that's totally okay.

31. Who is your hero? What qualities make them your choice?

The people you look up to say a lot about the person you are currently, as well as the type you'd like to become.

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32. What values do you think are critical to communicating to younger men?

How can we help tomorrow's men to succeed in all aspects of existence? What critical standards must be passed down?

33. What's the one thing that should be taught in school that isn’t?

Would he implement classes on how to prepare taxes and manage credit cards? Or maybe he would prefer more of the day was spent mastering the recorder?

34. Do you think artificial intelligence will end up benefiting, harming, or destroying humanity?

It's impossible to predict what the future will hold, but it's certainly interesting to talk about.

35. What bad habits have you already stopped?

There's always something to be proud of. Stopping a bad habit is an achievement.

36. Who was your role model in life?

If you want to have a meaningful connection with someone, it helps to know who they look up to. Chances are, they resemble that person a lot.

Grandmother and granddaughter bonding together

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37. Do you believe everyone has a talent?

It would depend on what people consider a "talent," right? Being able to sleep for the whole day might be considered a talent for some.

38. What kind of parent do you wish your kids remember you?

We all want to be remembered and be in people's lives, but how we want to be remembered says a lot about what we hold dear.

8 Best Deep Questions to Ask a Girlfriend

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There's always something new to learn about your partner in crime. These deep questions to ask your girlfriend help you to really understand what makes her tick.

Having deep conversations can really improve a relationship. It can strengthen existing bonds and create new ones.

Having questions to ask your girlfriend prepared keeps the relationship fun. After all, you don't want to spend your next dinner date sitting in silence.

Here are 8 of the best deep questions to ask a girlfriend:

39. Have you ever lost someone close to you?

This question can be difficult. If she doesn't want to talk about it, be an understanding boyfriend and change the topic.

40. Is there anything you’re ashamed of from your past?

Everyone makes mistakes. This is the right question to realize that. Is she willing to talk about them? It may help her to open up when you speak about your past errors first.

41. What were your family's views on race, ethnicity, and difference?

Learning about her family helps you to understand her better.

Family having a meal together

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42. Other than me, who in your life do you wish you’d met sooner?

This is a different way of asking who the people most important to her are. It helps you to understand the value that someone brings.

43. What is your love language?

It's an essential and good question to ask if you want to treat them right and know them deeper.

44. How important is intimacy in a relationship?

It's essential to be on the same page when it comes to this. We all have boundaries, and we want those we're in a relationship to understand and respect that.

45. What have you learned from your past relationships?

Whether the past relationship ended well or not, we all learn something from them. It's important to take that learning into the next one.

46. Is it possible to stay friends with your exes?

Not everyone can agree on one answer. The topic is always up for debate.

Couple sitting beside each other

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7 Best Philosophical Questions

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These fascinating questions can lead to new ways of viewing the world around you. Philosophy improves your critical thinking skills. It helps you to reason better.

Spending some time dwelling on these deep philosophical questions can really help you to unlock your own mind. These deep philosophical questions can give you those light bulb moments when everything just makes sense.

When you really want the conversation to get cooking, nothing beats philosophical questions. Just make sure you respect the other person's opinion, even if you disagree.

Here are 7 of the best philosophical questions to ask:

47. How important is freedom of speech in a healthy society?

Is there a limit to what should be allowed? Do they think being able to say anything is more beneficial or harmful?

48. Is it possible to be too creative to the point of insanity?

There's a fine line between using your mind and losing your mind. At what point do you cross that line? Can you think of examples of people who went too far?

49. Do dreams have meanings?

Or are they just neurons firing arbitrarily? Are our brains trying to tell us something?

50. Which is more real – mind or matter?

You can touch matter, but you wouldn't realize it without your brain. You can imagine anything, but if you can't touch it, is it even real?

51. What do we most need in this world?

Beyond the apparent air, water, shelter, and food, what do we really require to make it in this world?

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52. What is your biggest fear?

It's a common thought that we always want to know.

53. Do you think spirituality is important?

This will say a lot about who they are as an individual.

7 Deep questions to ask a new friend

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Getting to know a new friend isn't always fun and games. Sometimes, you have to bring out deep questions to ask a new friend to have more extensive knowledge of your friend.

Here are 7 deep questions to ask a new friend:

54. How do you feel about getting older?

You'll learn about your new friend depending on whether they're afraid or excited about it and why.

55. Do you have any tattoos? What is the meaning of each tattoo you have?

Sometimes, the tattoos we put on our bodies mean the deepest things in the world. It can be a mirror into our soul. Occasionally, we just think it's cute.

56. Have you ever felt like your world is falling apart?

If they say yes, be a friend and offer your time to listen to them.

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57. Do you believe in life after death?

It would also be nice to know what their concept of an afterlife is! Definitely a topic worth talking about.

58. What is the best piece of advice you have received from a friend?

Maybe you can make use of that advice, too! Whatever it is, it must be terrific and mind-blowing.

59. Did you regret giving your first kiss to someone?

If they could turn back time, would they still do that first kiss? Some would, some wouldn't. It's a good discussion to have.

60. Would you choose friendship over a romantic relationship?

We all have different views when it comes to these. Friendship and a romantic relationship are two very different dynamics, but both are very meaningful.

9 Best Existential Questions

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These existential questions can give your brain a serious workout. Existential questions are powerful. They force us to confront our humanity and who we are at our core. They make us consider the very essence of what it is and what it means to exist.

Asking too many of these can lead to the classic existential crisis, so use them sparingly.

Here are 9 of the best existential questions to ask:

61. What is the difference between living and existing?

This question really makes you examine whether you're just passing the time until you die or making the most of every day.

woman lazily lying on a park bench

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62. What are we a part of?

This conversation can get heady. Sure, we're part of a society, but think about humanity as a whole. Then the possibility of other lives in other universes. Keep going bigger until it hurts.

63. Where do you think we go when we die?

Do we go back to where we were before we were born? Another dimension? Are we reincarnated? Do our souls go to heaven or hell? Nobody knows, but it's certainly interesting to speculate.

64. Where do you think we come from?

Do you believe in a creator? Or are we here by pure chance? Do we exist simply because we must for the universe to be truly infinite? Are we part of a simulation? What is the origin of the human species?

65. Do you think a parallel universe exists?

If you asked an ant about the Milky Way, it wouldn't have an answer. Are we simply incapable of understanding the dimensions around us?

66. Do we have a greater purpose?

And once we figure it out, will we be capable of achieving it? Or are we simply pawns in a game controlled by superior cosmic beings?

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67. Where or what was your consciousness before you were born?

People always wonder about what happens after death, but what about before we existed? Were our souls waiting for our turn at bat? Or did they materialize as soon as we were conceived?

68. As a human, are you an outside observer of the universe, or are you a piece of the universe observing itself?

Is our greater purpose simply to observe the universe? We often view the universe as something outside of us, but an exciting possibility is that the universe is us.

69. Is time a construct of man or a rule of nature?

Is time a man-made invention to keep track of our place in the universe? A relative scale? A calculation of existence? An ever-flowing river of events? A fourth dimension? The engine that prevents the universe from remaining static? An undefinable phenomenon that morphs depending on an infinite number of factors? A scheme to sell watches?

8 Best Deep and Thought-Provoking Questions To Ask

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When you're ready to move from small talk to real talk, use these thought-provoking questions. These questions give your brain a workout, sparking deep discussions that enrich everyone involved.

These questions deserve attention. These aren't the type of questions you ask and then move on. Sink your teeth into them, and use them to feed other relevant, in-depth conversations.

At the same time, you must pay attention to how your conversational partner is responding. If they don't seem to be into it, move into lighter territories. Thought-provoking questions are best used sparingly, so save them for appropriate times with the right people.

Here are 8 of the best deep and thought-provoking questions to ask:

70. At what point is a technologically enhanced human not a human anymore?

Conversely, if you have an ax and replace its head and then replace its handle, is it still the same ax?

71. Suppose a child somehow survived and grew up in the wilderness without any human contact. How "human" would they be without the influence of society and culture?

Are we a product of our environment? Or is humanity ingrained in us?

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72. Would things get better or worse if humans focused on what was going well rather than what’s going wrong?

On a grand scale, is positive or negative reinforcement more effective for creating change?

73. Does the study of philosophy ever lead to answers or simply more questions?

Can we ever reach a final destination, or are conclusions always out of reach?

74. Does jealousy have value in driving humans to improve themselves or is it a purely negative emotion?

This question forces you to examine what's commonly viewed as a negative trait in a positive light.

75. What advice would you give your younger self?

We just hope that your younger self is someone that listens to advice from an older you.

76. If you were given a chance to play a favorite memory for the rest of your life, what would it be?

Our favorite memory, although dear to us, may feel bittersweet. However, there's a favorite memory that we wouldn't mind playing over and over again. Reliving the feeling will always feel great.

Friends in the middle of sunflower field

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77. Why do humans need love and affection?

This philosophical question will surely get both of you thinking deeper.

Downloadable and Printable List of Conversation Starters

Here is a downloadable and printable jpg/pdf list of deep questions to ask (right-click the image and select Save Image As…):

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Frequently Asked Questions

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Asking deep questions is something that we should do, but it's not always easy. We're here to help you and answer your questions.

Is it okay to ask deep questions to a new friend?

It's okay to ask deep questions to a new friend as long as you know to tread lightly. Ask politely, and let them know you'll be asking deep questions. Give them a choice not to answer if they're not comfortable. It's always great to have some deep questions to ask a new friend so you can know them better faster!

What are the benefits of asking deep questions?

Asking deep questions to your friends allows you to know them better. If you're able to understand them more profoundly and better, you'll have a better connection. This will help you be a better friend to them. Knowing deeper about other people also helps you look at the world from a different perspective. It's a way to widen your horizons.

How do I know if I'm asking the right questions that will let me know her better as a person?

As long as they don't become offended and awkward around you, you're doing fine. Always put a disclaimer before asking anything that might be too personal to ensure that you will harm no relationship.

How to Start a Deep Conversation: 5 Tips

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Starting a conversation can seem intimidating, but as long as you follow these tips, you'll be good to go.

Tip #1: Know your company

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A first date or hangout probably isn't the best time to start a deep conversation. Keep things lighthearted until you're confident that you're comfortable enough to have an in-depth discussion with them and also that they're equally as pleased with you.

Tip #2: The setting matters

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There's a time and place for everything. If you're chatting with someone at a mutual friend's birthday, these deep questions to ask aren't ideal conversation fodder. However, if you're on a third date gazing at the stars with a bottle of wine, these conversations can really help to make that connection. Knowing where to start a conversation is just as important as knowing how to start a conversation.

Tip #3: Pay attention to body language

Man and woman having a drink outside

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If who you're talking with doesn't feel comfortable, don't push it. Not everyone is willing to open up, and there's nothing wrong with that. Don't be offended if someone says they're not ready to talk about deep or personal topics.

Tip #4: Use deep questions sparingly

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These questions carry weight. Don't fire off one after the other. Ask one, and then use the person's response to dive into the sea of conversation. Don't just ask a question, listen to the answer, and move on.

Tip #5: Participate in the conversation

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One of the biggest mistakes you can make is keeping the conversation one-sided. If you want someone to feel comfortable opening up to you, you must open up to them too. It's a two-way street. You give, and you take. Deep questions should lead to deep discussions. This isn't an interview.

Looking for More Deep, Personal Questions to Ask?

By now, you should be a bona fide deep thinker. After a few serious conversations, you might feel like the next Plato or Carl Sagan.

Of course, once you've had a taste of the power of deep discussion, the thirst for more knowledge only grows stronger. Fortunately, we have plenty of other personal questions to ask, as well as some more lighthearted conversation starters.

  1. These straightforward get to know you questions help you to connect with someone. They're incredibly versatile, perfect when you're just starting to get to know somebody.
  2. When you just want some fun and laughs, nothing beats would you rather questions. It's a timeless game that never gets old.
  3. Whether you need something to talk about at dinner or you want to pass the time on a long car ride, these questions for couples are sure to spark some interesting discussions.

In Conclusion

Having a long list of solid deep questions to ask is the first step. We've done the hard part for you. Now, it's up to you to make those questions blossom into fascinating, engaging conversations.

Take these questions to ask seriously. If someone opens up to you, it's a privilege and a learning opportunity.

Be open-minded, empathetic, and understanding. Try to understand the other person's perspective and not be afraid to shift your beliefs and views, even if they're deep-rooted. Above all, listen. If you're going to ask a deep question, you must give the other person plenty of breathing room to provide a well-thought-out answer.

Answering deep questions can be a little scary. Be a respectful and attentive listener, and you can be sure your company will be appreciative.



40 Thought-Provoking Questions to Get to Know Your Family

Think you know everything about your family members? Chances are, you probably don’t. 

Jump ahead to these sections:

What if you were to ask more family questions? Just think about what you could uncover. You could learn the ways family members remember past events. You could get a new appreciation for family stories from their point of view. You could even discover things about their lives you never knew.

Funny questions like "What's the craziest thing you've ever done?" or informative ones such as "What did you find rewarding and challenging about being a parent?" are great family questions to get the conversation going.

Funny Questions to Ask Family Members

Having a family reunion? Looking for a new twist on family game night? Asking your family members funny questions can be a great ice breaker or a fun way to pass the time. We’ve pulled together a list of fun questions to help you get to know your family members better.

1. “When you were a teenager, what got you into trouble?”

You may view your parents and grandparents as only disciplinarians or authority figures. Find out about their hidden rebellious sides.

2. “Did you ever play pranks on your siblings?”

Siblings may seem like they’ve been put on this planet just to drive you crazy. Ask about sibling rivalry from prior generations. 

3. “Did you ever have a run-in with the law?” 

Your parents and grandparents try to teach you right from wrong but they might not always have been on the right side of the law!

4. “What’s the craziest thing you’ve ever done?”

Not all parents share the adventures of their misspent youth freely. These stories can make for fun and wild stories once you’ve grown up. 

5. “What was the worst job you ever had?”

We’ve all had to work terrible jobs. You might be surprised to learn about your dad’s chicken farming days. 

6. “Do you have any hidden talents?”

People usually like to talk about things they’re good at. But some talents might be under your radar.

7. “Did you ever hide things from your own parents?”

You can learn a lot about your parents or grandparents by finding out what they wanted to hide. 

8. “What’s the silliest thing you’ve ever done?”

You might not be able to imagine your parents or grandparents being goofy. This can let you know about a whole new side of them. 

‘How Well Do You Know Me?’ Family Questions

How well does your own family know you? These questions can help your family members gain some better insight into who you are.

9. “What’s a major event you remember from my childhood?”

We all have events that have made a huge impact on us. You can see how well your family remembers the formative events that made their mark on you.

10. “What was my favorite book when I was little?”

Your parents may do things before you can formulate concrete memories. This might include reading to you every night. Asking your parents might help tap into new memories of your own. 

11. “What did I want to be when I grew up?”

When you’re a kid, it seems like everyone asks you about your future plans. See how closely your parents paid attention to your aspirations.

12. “When I was a teenager, what is the thing I did that upset you the most?”

Teenagers excel at pushing boundaries. See how your parents’ memories of your teenage years stack up against your own.

13. “What are your first memories of me?”

Parents actually remember things about your life that you don’t. This question can illuminate a lot about your parents’ earliest memories of you. 

14. “Who was my first crush?” 

You don’t always let your parents in on your inner lives when you’re young. See if your parents were paying attention anyway.  

15. “What do you think is my biggest talent?”

You don’t always see yourself the way others view you. Here, you can find out about how others perceive your strengths. 

16. “What do you think is my favorite book/TV show/movie?”

See how well your family understands where your interests lie.

Questions to Ask About Family History and Stories

Your parents and grandparents have access to so many memories you’ve never heard. Check out these questions to ask older people and reach out to your family members. You may be surprised by what you find out. 

17. “Of all the things your parents taught you, what do you think helped you the most?”

Asking this question can help you learn about the priorities in multiple generations of your family. It can also give you insight into what shaped your parents growing up. 

18. “Do we have any famous or infamous people in our family tree?”  

Odds are you would have heard about famous relatives if they were notable for something good. Your parents and relatives might have avoided talking about someone more nefarious. Now is a good time to learn some unsavory family history.

19. “How did Grandma and Grandpa meet?”

You may know how your parents met. Grandparents may be a bit more of a mystery. 

20. “What is your favorite memory of your parents or grandparents?”

Grandparents and parents were once kids, too. Learning more about their childhood can help you connect.

21. “What family member were you closest to growing up?”

Sometimes the best way to get to know someone is by learning about that person’s relationships.

22. “How did some of our family traditions originate?”

You may have rituals you engage in without even realizing it. Maybe every year for Christmas your grandma makes a special cake. Ask for the stories behind those particular traditions in order to understand them better. 

23. “What family traditions have we let lapse that you’d like to bring back?”

Certain things may fall to the wayside as you grow older. See if certain childhood traditions can be revived for grandchildren.

24. “What family members do you wish I would have gotten to know?”

Sometimes grandparents or great-aunts pass away when you’re young. See if your family is ready to open up about those you’ve lost.

Great Questions to Ask Around the Family Dinner Table

Add a fun element to a family meal — ask some questions around the dinner table.   

25. “What did you find most rewarding and most challenging about being a parent?”

As you grow older, you develop more of an appreciation for what your parents dealt with to raise you. Find out more about their thoughts from that time.

26. “Were there things you swore you would never do as a parent that you actually ended up doing?”

They say the most confident parents are the ones who don’t have children yet. Learn how your own parents adjusted their expectations.  

27. “How did you balance work and family life when I was a kid?”

It’s a struggle to maintain boundaries. Find out how your parents handled that challenge. 

28. “What family traditions have we let lapse that you’d like to bring back?”

Yes, this is the same question for earlier, but it’s a great question in this context!

29. “What do you think is the secret to a long and happy relationship?”

Have your parents or grandparents been together for many years? Discover the secret to their success. 

30. “What do you think our family motto should be?”

Some families have a code that they live by. It can be a fun exercise to put that into words. 

31. “What was your first car?”

Cars from older generations seem much cooler than what’s on the road today. Find out what your parents or grandparents rode around in during their youth.

32. “Who has had the biggest influence in your life?”

You can learn so much about the people who inspire you by discovering who inspired them.

Other Great Questions to Ask Your Family

So far, we’ve given you some questions to ask your family under particular circumstances. But there are questions that are good for any occasion. Whether you’re constructing a family tree or looking to pass time on a road trip, these questions are sure to be entertaining and informative. 

33. “What do you know now that you wish you had learned earlier in life?”

Sure, you need to learn some things yourself in your own time. But it’s undeniable that your life would have been easier had you figured some of these things out sooner. 

34. “What did you want to be when you grow up?”

You have dreams when you’re young. Hearing about other people’s early dreams can give insight into who they are.  

35. “What’s the biggest challenge in your life that you had to overcome?”

Adversity can really shape people. Find out what obstacles your family members have had to tackle in their lives. 

36. “What’s a piece of advice that you wish you had taken?”

It’s easy to hear good advice, then never take it. Examining the whys can be illuminating for everyone. 

37. “Do you have any advice on getting through personal struggles?”

Finding out how people pushed past their hardships can be inspirational. 

38. “Can you tell me about your first love?”

Your parents may not have always been together. They likely dated other people first. See what you can discover about those relationships. 

39. “What was your wedding like?”

Find out how your parents began their love story.  

40. “Who is the best friend you’ve ever had?”

You can learn a lot about a person by the company he or she keeps. 

Get to Know Your Family Better with These Informative and Entertaining Questions

When you’ve spent your whole life with your family, it’s easy to feel like you know everything about them. But people have long memories and rich inner lives. There are many things you’ll never learn about them unless you ask. These questions can help reveal untold surprises about the people you love. 

Post-planning tip: If you are the executor of a deceased loved one's estate and you didn't get a chance to ask the important questions, we have a post-loss checklist that will help you ensure that your loved one's family, estate, and other affairs are taken care of.

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Subscribe to Connect in a more meaningful way

Modern life is very busy, and it’s easy to find distractions from those more meaningful questions that float into our minds (usually while we lay awake in bed!). But that doesn’t mean we don’t all have our own thoughts, ideas and philosophies. We tend to conceal these thoughts and feelings, thinking that they’re too personal to share and that nobody would be interested in hearing them.

An effective way to get to break through superficial conversations and get to know someone else on a much deeper level is by asking personal questions that bring to surface these deeper ponderings. The next time you are unwinding with a colleague or a close friend, try asking them a personal question and see if they’re willing to share. You may find that by giving them an outlet to talk about themselves, they may find it therapeutic. If you pay attention and listen, you’ll also learn more about them, boosting your relationship with them to a deeper level.

Sometimes it takes a bit of icebreaking to get to more personal questions. If you sense the mood is a bit too stiff, then play a round of Brightful Meeting Games first. It will be sure to loosen everyone up and prime them for more meaningful relationship building.

92 Very Insightful Personal Questions to Ask

Asking the right insightful question is a great way to get to know someone on a deeper level. If you're looking to have some great conversations, the best way by playing Question of the Dayon Brightful.

Thought provoking prompts are automatically generated and there is a timer for everyone to speak. You can invite friends, colleagues or family from anywhere across the world. The best part is that it's free!

1. Why are you passionate about what you do?

2. Where do you see yourself in 5 years’ time?

3. What do you think makes a good leader?

4. Do you think money is important?

5. What makes you the happiest?

6. What is the most surprising fact you’ve learnt about yourself?

7. What are you afraid of?

8. What is your personal philosophy in life?

9. What do you think your role is in this world?

10. What do you believe is true about human nature?

11. When it comes to your work life, how much is due to your hard work and how much to the environment?

12. Who is your hero?

13. How do you spend your time?

14. What do you wish you had asked your parents before they passed away?

15. What is the best and worst advice you have received?

16. What does it mean to you to make a difference in the world?

17. Do you think that education is important?

18. Where is the best place in the world you’ve ever been to?

19. What are you most proud of?

20. Where is there room for improvement in your life?

21. What do you think is the most beautiful thing you’ve ever seen or experienced?

22. How do you balance your personal and professional life?

23. What do you think makes a great leader?

24. What are you most thankful for?

25. What is the biggest decision you’ve had to make?

26. What has impacted you the most?

27. Does listening to music affect you, and how?

28. What does your daily routine look like?

29. What was the worst phase in your life?

30. What do you believe is most important for happiness in life?

31. How do you spend your weekend?

32. What is your favourite movie or book series?

33. What were the best experiences and events that happened to you in the last 12 months?

34. What are you most passionate about?

35. What do you do when life gets hard?

36. What do you do to combat negative thoughts in your life?

37. What do you want to be known for after you die?

38. What makes you different from others?

39. How does it feel to be your age?

40. How would you define success?

41. What is the difference between ordinary and extraordinary?

42. How would you describe your personality?

43. What do you hope to accomplish in the future?

44. How is your relationship with your parents?

45. What is the first thing you think of when you wake up?

46. Do you like being able to communicate with others through social media?

47. What is your favourite book?

48. What motivates you in life?

49. Who is your role model?

50. How does your family feel about your work?

51. How do you feel about your relationships?

52. What are you most grateful for in your life?

53. What is the most important lesson you learnt in life?

54. How do you balance work and leisure?

55. Do you hold any convictions that you are willing to die for?

56. What is the biggest regret you have in your life?

57. Where is your favourite place to relax?

58. What inspires you?

59. How would your friends describe you?

60. What are you afraid of?

61. Is money important to you?

62. What do you do to de-stress?

63. What is a quality you admire in others?

64. Would you relocate to a place where you don’t have any family or friends?

65. How do you make decisions?

66. What is your greatest achievement?

67. How do you feel about your relationships with your family?

68. Where are you currently in your life?

69. Do you think that technology is improving lives?

70. What’s your favourite quote?

71. Who do you look up to?

72. What do you do in order to keep your friends and family close?

73. How do you react to your own mistakes?

74. What are your ambitions in life?

75. What was the best phase in your life?

76. What is your favorite quote and why?

77. Who has influenced you the most?

78. What is the hardest thing you’ve ever done?

79. Who inspires you?

80. What do you like doing in your free time?

81. How do you react to change in your life?

82. What is the biggest obstacle/challenge you are facing right now?

83. How do you live a productive life?

84. What qualities do you think are important in a family?

85. How important is your family to you?

86. What book and movie spoke to you, and in what way?

87. What do you think of your generation?

88. What will people say about you at your funeral?

89. What is one thing you want to let go of this year?

90. What was the last place you went to?

91. What do you think is the purpose of life?

92. If you were going to have an operation, what would your operation be about?

10 Philosophical Questions that will Change Your Life

Whether you are attending a formal family reunion or just a casual meal together, gatherings are an excellent opportunity to learn more about both immediate and extended family members. These are great questions you might ask your dad, your great-aunt, or even the spouse of your third cousin, once removed!

A Link to the Past

The chance to sit down and chat with your elders can reveal a lot about your family history and what life was once like.

  • Tell me about what it was like growing up in [name of place].
  • Did you live in a house or an apartment? Was there electricity and indoor plumbing?
  • Where is the family originally from? How far up the family tree can you go?
  • Who is the oldest family member you remember, and what do you remember about them?
  • What was a typical family dinner like for you?
  • As a kid, what did you think you wanted to be when you grew up?
  • What stories did your grandma/grandpa used to share about their younger years?
  • How much was your allowance, and how did you choose to spend it?
  • Do you think life is easier or harder for kids these days compared to your childhood? Why?
  • What do you think is the most important life skill or value your parents taught you?
  • Have you ever gone back to visit your childhood home? What about where your mom or dad grew up?
  • What single invention had the biggest impact on your life?
  • Are there any treasured family heirlooms? What's the story behind them and who has them now?
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Playing Favorites

You can learn a lot about someone by asking them about their taste in entertainment and other favorites. These are some of the most fun questions to ask family because you'll likely reveal generational divides that are ripe for friendly debate.

  • What kind of music did you enjoy when you were younger? Do you still like it now?
  • Do you remember a favorite dish your mom/dad/grandparent used to prepare? Can you make it now?
  • What was your favorite TV show growing up? What is it now?
  • What was your favorite toy as a child? How did you get it?
  • Who was your biggest idol or role model as a teenager?
  • Who was your biggest celebrity crush as a teen?
  • Where is your favorite all-time vacation spot? How many times have you been there?
  • What was your favorite childhood treat? Do you still like it now?
  • Is there something from your childhood you wish was still popular today?
  • What are your top three all-time favorite movies?

Reminiscing Over Story Time

Everyone has a great story to tell. You just have to ask the right questions to get them talking.

  • How did you ever get your nickname? Did you have a nickname growing up that no one calls you anymore?
  • Where did you go to school and what was it like? What were your most and least favorite subjects?
  • What is your earliest childhood memory? Why do you think it sticks out for you?
  • How did you and your friends spend your time after school and on weekends?
  • Where was your first job and what did you do? Was it fun? What did you learn?
  • What was the most unique or interesting summer job you ever had?
  • What's the worst trouble you've ever gotten yourself into? How did you get out of it?
  • What is the scariest thing you've ever done?
  • How did you react when you found out you were going to become a parent for the first time?
  • Were your parents more authoritarian or more lenient? Do you think this affected your parenting style?

Questions of Why

Understanding motivations and decisions made along the way can illuminate incredible insights into the lives of your family members.

  • Why did your parents decide to name you [full name]?
  • How did you decide on the names for your own children?
  • Why did you finally choose to settle down where you did?
  • Did you ever dream of living somewhere else?
  • What got you to decide on your current career? Did you always think you were going to do this for a living?
  • Why did you decide to go or not to go to college/university?

It's a Family Affair

These questions can serve as tremendous conversation starters, offering a glimpse into the past and where your family came from. The next time you ask your aunt to pass the scalloped potatoes, you might also ask what your grandma was like as a mother herself!

© 2021 LoveToKnow Media. All rights reserved.


Questions family ask deep to

Sometimes, you meet someone, and you just click. You feel like you've been besties your entire life and honestly can't believe there was a time when you didn't even know they existed. And then, there's those other relationships that take a little more work—i.e., how it feels like pulling teeth to learn anything about your brother-in-law. While you might never be BFFs with your BIL, there is a trick you can use to get him to open up a little more.

Terri Orbuch, PhD, author of 5 Simple Steps to Take Your Marriage from Good to Great, says getting to know someone starts with the "breadth questions"—think: impersonal but important biographical info about a person's family, their career, and if they’re single or married, for example. (Although if you're asking these q's of your BIL... you should definitely know the answer to that last one.)

Tamekis Williams, LCSW, founder of Mission Dorothy Female Empowerment Services, adds that you want to ask open-ended questions that will allow the other person to elaborate, instead of questions that can be answered with a simple "yes" or "no."

After all, if you really want to get to know someone beyond the surface level, you’ve got to dig deeper. "Topics that get at the other person's inner world—their thoughts, goals, and dreams—will strengthen and increase bonding between two people," Orbuch notes. "Sharing personal information strengthens any relationship, and deeper questions focus on that personal self-disclosure."

Btw, that's a two-way street, adds Williams. "When initially meeting someone, it is important to be inviting and warm so that the other person can initially feel comfortable talking with you."

On that note, Williams suggests taking a careful approach in your questions, as you don't want the other person to feel like you're violating their privacy. Questions you should probably steer clear of early on: "Democrat or Republican?" "Do you own or rent?" and "What is your faith or spiritual belief?".

There are other ways to bypass small talk and learn more in-depth info about the other person, says Williams. "You can get the answers [you're looking for] by sometimes answering those questions yourself while sharing about you. An example would look like: 'I just moved to Georgia last year and found a beautiful community that I fell in love with and purchased a home. What about you, do you love where you live?'"

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With a little patience, you'll become way closer with the person you're just getting to know in no time. Here are 200 not-boring questions to get you started:

"Asking someone about their preferences helps you to understand who they are as a person," says Rebecca Hendrix, a therapist in New York. The important thing here is to go deeper by asking follow-up questions.For example, "If you find out they like dogs, take it a bit deeper by asking them what they like most about their dog or their favorite breed," Hendrix explains.

"Commonalities often open the door for further conversation and, once that door is open, you can start a dialogue that allows the other person to elaborate and not give close-ended answers," Williams adds.

Some other ideas:

1. What’s your favorite way to spend a day off?

2. What type of music are you into?

3. What was the best vacation you ever took and why?

4. Where’s the next place on your travel bucket list and why?

5. What are your hobbies, and how did you get into them?

6. What was your favorite age growing up?

7. What was the last thing you read?

8. Would you say you’re more of an extrovert or an introvert?

9. What's your favorite ice cream topping?

10. What was the last TV show you binge-watched?

11. Are you into podcasts or do you only listen to music?

12. Do you have a favorite holiday? Why or why not?

13. If you could only eat one food for the rest of your life, what would it be?

14. Do you like going to the movies or prefer watching at home?

15. What’s your favorite sleeping position?

16. What’s your go-to guilty pleasure?

17. In the summer, would you rather go to the beach or go camping?

18. What’s your favorite quote from a TV show/movie/book?

19. How old were you when you had your first celebrity crush, and who was it?

20. What's one thing that can instantly make your day better?

21. Do you have any pet peeves?

22. Which meal is your favorite: breakfast, lunch, or dinner?

23. What song always gets you out on the dance floor?

24. When you were a kid, did you eat the crusts on your sandwich or not?

25. What activity instantly calms you?

26. Ideally, how would you spend your birthday?

27. What do you do on your commute to/from work?

28. Are you a fan of musicals—why or why not?

29. What's your favorite season and why?

30. What's the best joke you've ever heard?

Questions can help deepen any relationship, but you should never have to ask these ones if you're in a healthy relationship:

31. What's the phone app you use most?

32. Would you rather cook or order in?

33. Have your ever disliked something and then changed your mind?

34. What's your favorite board game?

35. How do you take your coffee?

36 What's your most prized possession and why?

37. Is there any product that you couldn't live without?

38. Do you sleep with a top sheet? Why or why not?

39. If you could have any exotic animal as a pet, which would it be?

40. What would be the first thing you'd do if you won the lottery?

41. What’s your favorite way to unwind?

42. How do you enjoy spending your alone time?

43. What’s the best concert you’ve ever been to?

44. Do you have a favorite type of exercise?

45. What causes are you passionate about?

46. What’s something you’re excited about right now?

47. What’s your favorite content genre (horror, sci-fi, rom-com, etc.)?

48. What’s an essential part of your daily routine?

49. What’s the best gift you’ve ever received?

50. What’s the worst gift you’ve ever received, and what did you do about it?

No matter how a person feels about his or her job, the fact is, tons of people spend a lot of time and energy at work. To help you get to know someone better, "facilitate a conversation where you are left knowing how they feel about their career," Hendrix says.

Just prepare yourself to return that openness when they ask the same of you and your work life. "Initial conversations set the tone for if the person wants to continue to get to know you, so be ready to answer some questions as well," Williams says.

Try out these convo-starters:

51. If you could choose your own work schedule, would you?

52. Is there one job you’d never ever do?

53. What’s the first thing you do after getting home from work?

54. Who or what inspires you in your career?

55. How do you approach taking time off from work?

56. What’s something an outsider wouldn’t know about your industry?

57. Do you have a morning routine at work? If so, what it’s like?

58. What’s your commute to work like?

59. Are you able to work from home, and if so, do you enjoy it?

60. Do you get along with all your coworkers?

61. What’s your favorite thing about your current job?

62. What annoys you most?

63. What’s the career highlight you’re most proud of?

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64. Do you think you’ll stay in your current gig awhile? Why or why not?

65. What type of role do you want to take on after this one?

66. Are you more of a "work to live" or a "live to work" type of person?

67. Does your job make you feel happy and fulfilled? Why or why not?

68. How would your 10-year-old self react to what you do now?

69. What do you remember most about your first job?

70. How old were you when you started working?

71. What’s the worst job you’ve ever had?

72. What originally got you interested in your current field of work?

73. Have you ever had a side hustle or considered having one?

74. What’s your favorite part of the workday?

75. What’s the best career decision you’ve ever made?

76. What’s the worst career decision you’ve ever made?

77. Do you consider yourself good at networking?

78. What career advice would you give to your younger self?

79. Do you believe in having a "five-year plan"?

80. How do you separate your work life from your home life?

81. When will you know you've "made it"?

82. Are you looking forward to retiring, or do you plan to work as long as possible?

83. Have you ever had "imposter syndrome"?

84. What do you think about workaholics?

85. What qualities do you look for in a boss?

86. Do you have a professional mentor? If not, do you want one?

87. What energizes you about your career?

88. Are you into after-work happy hours?

89. How do you motivate yourself in your career?

90. What's the best career advice you've ever heard?

91. What's the worst career advice you've ever received?

92. When you started your current job, what most surprised you?

93. How do you pick yourself back up after making a mistake at work?

94. How do you deal with work stress?

95. Do you have a work bestie?

96. What's one work-related thing you want to accomplish in the next year?

97. Who has had the biggest impact on your career choice?

98. What does your family think of your career?

99. What's the best thing you've learned in your current position?

100. If you could do it all over again, would you pursue the same career? Why or why not?

A great way to get to know someone on a more personal level? Learn about the people they love. "Asking questions about close relationships can lead to stories, and sharing stories leads to connection and an experience of being seen by one another," Hendrix explains. Try:

101. How much time do you spend with your family?

102. Who do you most like spending time with and why?

103. Which family member makes the best food?

104. How has your opinion of your family changed over the years?

105. If you’re close with your family, what’s the hardest part about spending time away from them?

106. Do you wish you had a bigger family, or are you happy with its current size?

107. Which family member has had the greatest impact on you?

108. What does your family’s last name mean? (Look it up if you don’t know!)

109. Who’s the best gift-giver in your family?

110. What’s your favorite story about your grandparents?

111. Have you ever mapped out your family tree?

112. Were you close with your family growing up?

113. How do you define your family now?

114. What traits are most important to you in your family members?

115. Who in your family makes you feel the safest?

116. Do you want a family of your own?

117. Have you ever been to a family reunion?

118. If you could change your relationship with a family member, would you? If so, with whom?

119. What was it like growing up as the youngest/oldest/middle/only child?

120. Does your family ever take trips together?

121. What’s your favorite family memory?

122. What TV family most reminds you of your own?

123. Do you ever wish you were raised differently?

124. What’s the best piece of advice a family member has given you?

125. Do you wish you had more siblings? If so, why?

126. Did you ever hide anything from or lie to your parents?

127. If you had a family business, what would it be?

128. Do you and your family have any nicknames for each other?

129. What's your favorite way to spend time with your family?

130. How do you show your family you love them?

131. What’s your favorite family tradition?

132. What's the most important holiday you spend with your family and why?

133. Who in your family would you describe as a "character"?

134. How do you feel about family events?

135. What's something your family would be surprised to learn about you?

136. Which family member do you confide in most?

137. How do you deal with arguments between family members?

138. If you have children, how do you want to raise them?

139. What's more important: family or friends?

140. Do you have any friends you would consider family?

141. Has your family ever pressured you to act a certain way?

142. Did you ever get to meet your great-grandparents?

143. What personality traits do you share with your relatives?

144. What physical traits do you share with your relatives?

145. What stories did your family members tell you growing up?

146. How did your parents (and/or grandparents) meet?

147. What makes you proud of your family?

148. Who's the newest member of your family?

149. What can always bring your family together?

"In learning about someone’s values, you are learning about their owner’s manual," Hendrix explains. Even seemingly mundane questions can get at a person’s values—like what’s motivating them to do well on a presentation or what they look for in an S.O.

"By learning about someone’s life philosophy, you're able to get at their true essence, how they live their life, and what drives their actions," Orbuch adds.

That said, you can't just ask, "What are your values?". What you can ask:

150. What do you think makes someone a “good person”?

151. Do you believe in love at first sight?

152. How do you show kindness to others?

153. Do you believe in soulmates? Why or why not?

154. What do you look for in a friendship?

155. How do your daily priorities reflect your overall values in life?

156. Do you believe time you enjoy wasting is not wasted time?

157. What life lessons have you had to learn the hard way?

158. Do you believe what is meant for you will never miss you?

159. Have you ever experienced true love, and how did you know?

160. What’s a relationship deal breaker for you?

161. If you had only one sense (hearing, touch, sight, etc.), which would you want?

162. Do you volunteer at all?

163. What makes you feel at peace?

164. What are you most proud of in the last year?

165. What makes you feel most accomplished?

166. Who do you admire most in the world?

167. Would you rather make more money doing a job you hate or less doing one you love?

168. Which of your personality traits are you most proud of?

169. What’s the first thing you look for in a partner and/or friend?

170. How has your perspective on the world changed over time?

171. Do you live by any piece of advice or motto?

172. How can someone earn your trust?

173. How can someone lose your trust?

174. Would you rather someone be honest and hurt your feelings or lie to protect them?

175. If you could snap your fingers and instantly make the world better, what would you do?

176. Do you believe in astrology? Why or why not?

177. Have you ever lost a friend? If so, what happened?

178. If you could only teach one thing to your (future) child, what would it be?

179. What’s the scariest thing you’ve ever done, and why did you do it?

180. Do you believe in second chances?

181. Where do you get your news?

182. What is your biggest irrational fear?

183. Are you active on social media, or do you prefer to be more private?

184. What is your definition of success?

185. Are you an organ donor, and how did you come to that decision?

186. Do you believe you should do one thing a day that scares you?

187. What, if anything, do you think happens after death?

189. What line should someone never cross with you?

190. How do you define beauty?

191. Do you believe in life on other planets?

192. How do you interact with someone who disagrees with you?

"These questions get at what the person is motivated by," says Orbuch. "What gives them the strength to wake up every day and get going? What do they dream and think about in their day?" When you learn about someone’s dreams, you share something more intimate. Jumpstart a deep conversation by asking this:

193. Do you think our dreams have hidden meanings?

194. When you want to give up, what keeps you going?

195. Do you live by any words of wisdom?

196. What's the first step you take in trying to achieve a new goal?

197. How do you turn a “no” into a “yes”?

198. What do you do to overcome a personal setback?

199. Is it easy for you to accept help in achieving your dreams?

200. If you could do anything, besides what you're doing now, what would you do?

201. What do you regret not doing in the last year?

202. What’s on your bucket list?

203. If you had unlimited money to start your own business, what would it be?

204. If you found out today was your last day on Earth, what would you do?

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

206. If you could relive one moment in your life, which would it be?

207. If you had the opportunity to be immortal, would you take it?

208. Which famous person in history would you want to spend the day with?

209. If you could time travel, when and where would you go?

210. Do you think you'll likely accomplish all your dreams?

211. If you could magically become famous, would you want to?

212. A genie gives you three wishes—what are they?

Sometimes the oddball questions allow you to learn the most interesting things about a person. "Unusual questions allow you to see the varied, unique, and special qualities of a person—their answers give you personal information about what makes them tick," Orbuch says. "These questions also typically get the other person to think outside box and really ponder something."

But you still want to keep things PG, says Williams. "Be careful with asking questions of a sexual nature too early," she advises. Same goes for the unconventional-for-a-reason q's, a.k.a. anything related to another person's finances, but especially questions about child support, debt, and credit score.

Ask these ~unconventional~ questions, and you'll definitely get some interesting (in a good way!) answers:

213. Do you believe in ghosts—why or why not? (Bonus question: If so, are you afraid of ghosts?)

214. Do you have any special skills?

215. Are you double-jointed?

216. What’s your game plan in a zombie apocalypse?

217. Can you write in cursive?

218. If you could live in a movie, which one would it be and why?

219. What’s your “dance like nobody’s watching” song?

220. Do you sing in the shower?

221. Are you good at solving puzzles?

222. How many hours do you get to the airport before a flight?

223. Can you say your ABCs backwards?

224. If you see a puddle on the ground, do you walk around it or over it?

225. If you could have a super power, what would it be?

226. If you could go back to anytime in history, where would you go?

227. If you came back in your next life as an animal, what animal would you be?

228. If you got to name a new country, how would you decide what to call it?

229. What would be the title of your memoir?

230. Do you hit the snooze button or wake up immediately?

231. What’s the first thing you do in the morning?

232. What’s the last thing you do at night?

233. Do you believe in any conspiracy theories (no judgement)?

234. Do you think iced coffee should only be consumed in the summer or all year round?

235. Would you rather be covered in fur or covered in scales?

236. What’s your idea of a perfect date (yes, of the calendar year)?

237. What’s the most unusual place you’ve fallen asleep?

238. At a party, where can someone find you?

239. Do you wash your legs in the shower?

240. Who would play you in the movie of your life?

241. When making a PB&J sandwich, do you put on the peanut butter or jelly first?

242. Do you have any allergies?

243. Do you trust your own memory? Why or why not?

244. Which fictional character do you relate to most?

245. What, if anything, would make you walk out in the middle of a movie?

246. When was the last time you cried and why?

247. What's your most controversial opinion about something mundane?

248. Do you "stan" any celebrities?

249. What's your go-to midnight snack?

250. What was your all-time favorite Halloween costume?

251. What's the weirdest thing you do when you're alone?

252. Do you have any recurring dreams?

253. What's the silliest argument you've ever been in?

254. What's the worst argument you've ever been in?

255. What's your opinion on modern art?

256. What's the most ridiculous outfit you've ever worn?

257. If you could own a mythical creature (unicorn, phoenix, etc.), which one would you pick?

258. Would you rather have your dishes or clothes be magically clean?

259. What's your favorite story about yourself?

260. If you could change anything about yourself, would you? If so, what and why?

"Anytime you reveal personal information to someone else, it increases intimacy between you and the other person," says Orbuch. So let down your guard, and don't be afraid to ask (and answer!) these deep questions.

Jasmine GomezAssociate Lifestyle editorJasmine Gomez is the associate lifestyle editor at Women’s Health and covers health, fitness, sex, culture and cool products.

Lindsay GellerLindsay Geller is the Love & Life Editor at Women’s Health, specializing in entertainment news and culture coverage.

This content is created and maintained by a third party, and imported onto this page to help users provide their email addresses. You may be able to find more information about this and similar content at

Asking My Husband *JUICY* Questions Girls Are Too Afraid To Ask - the east fam

120+ Deep Conversation Starters to Spark a Meaningful Discussion [2020]

These deep questions are the perfect questions to get to know someone. If you meet someone you feel an immediate connection with, ask them these deep questions to get to know them on an intimate level as quickly as possible.

Questions To Ask If You Want To Get To Know Someone On A Deeper Level

1. What’s your philosophy in life?

2. What’s the one thing you would like to change about yourself?

3. Are you religious or spiritual?

4. Do you consider yourself an introvert or an extrovert?

5. Which parent are you closer to and why?

6. What was the best phase in your life?

7. What was the worst phase in your life?

8. Is what you’re doing now what you always wanted to do growing up?

9. What makes you feel accomplished?

10. What’s your favorite book/movie of all time and why did it speak to you so much?

11. What is a relationship deal breaker for you?

12. Are you more into looks or brains?

13. Would you ever take back someone who cheated?

14. How do you feel about sharing your password with your partner?

15. When do you think a person is ready for marriage?

16. What kind of parent do you think you will be?

17. What would you do if your parents didn’t like your partner?

18. Who is that one person you can talk to about just anything?

19. Do you usually stay friends with your exes?

20. Have you ever lost someone close to you?

21. If you are in a bad mood, do you prefer to be left alone or have someone to cheer you up?

22. What’s an ideal weekend for you?

23. What do you think of best friends of the opposite sex?

24. Do you judge a book by its cover?

25. Are you confrontational?

26. When was the last time you broke someone’s heart?

27. Would you relocate for love?

28. Did you ever write a journal?

29. What are you most thankful for?

30. Do you believe in second chances?

31. What’s the one thing that people always misunderstand about you?

32. What is your idea of a perfect vacation?

33. What did your past relationship teach you?

34. What are your thoughts on online dating or tinder?

35. What’s on your bucket list this year?

36. When have you felt your biggest adrenaline rush?

37. What is the craziest thing you’ve ever done and would you do it again?

38. If a genie granted you 3 wishes right now, what would you wish for?

39. What’s your biggest regret in life?

40. What do you think about when you’re by yourself?

Get To Know Someone
The remaining bonus questions were written by a collective author, and not Rania Naim

Questions To Ask Someone If You’re Just Starting To Get To Know Who They Really Are

41. Does your job make you happy?

42. What did you want to be when you were younger?

43. Why did your last relationship end?

45. What’s been your biggest mistake so far in life and what did you learn from it?

46. Where is your favorite place in the entire world to go?

47. What are your top five favorite movies?

48. What are some of your favorite songs?

49. What qualities do you admire about your parents?

50. How would you describe your best friend?

51. What’s your favorite hobby to do alone?

52. What’s something you can’t go a day without doing?

53. What’s the most spontaneous thing you’ve done lately?

54. What’s the craziest thing you’ve ever done for love?

55. What’s your biggest pet peeve?

56. Why do you think you’re still single?

57. What accomplishment are you most proud of?

58. What is one dream you have yet to accomplish?

59. What is your greatest fear?

60. What are three things you value most about a person?

61. Who are five people you are closest with?

62. What is the greatest struggle you’ve overcome?

63. If you could live anywhere in the world where would it be?

64. What’s the most exciting thing that’s happened this past year?

65. What’s your favorite beer?

66. What’s one thing that bothers you most about the world today?

67. Who are you closer with your mom or your dad?

68. If you could change one thing about yourself what would it be?

69. If you could change one thing about the world what would it be?

70. Who was your favorite teacher and why?

71. What sport did you fall in love with?

72. What is the weirdest thing about you?

73. What was your longest relationship?

74. What would your best friend say is your best quality?

75. Who is your favorite historical figure?

76. What made you choose the college you went to?

77. If you could tell your former self one thing right now what would it be?

78. What food could you not live without?

79. Dogs or Cats?

80. What’s closest you’ve ever come to being arrested?

81. What was your best birthday?

82. What’s one thing you wish you knew how to do?

83. Where’s one place you’d like to go that you haven’t been?

84. What was the last book you read? And When?

85. Where do you usually get your news?

86. What are some of your own personal goals in the next 5 years?

87. What would you consider your greatest accomplishment so far?

88. If you could get away with anything that you do?

89. Who is your greatest hero?

90. What’s the greatest risk you’ve ever taken?

Questions To Ask Someone If You Want Them To Bare Their Soul

91. Why are we here?

92. If heaven is real and you died tomorrow, would you get in?

93. Do you believe in fate?

94. How do you think people see you?

95. If you had the ability to erase something that you did in the past, what
would it be?

96. What song makes you unconditionally happy?

97. If you could have anybody else’s life, who’s would you take?

98. What fictional character do you most relate to?

99. If I asked you at age 5 what you wanted to be when you grew up, what would you say?

100. What is your biggest irrational fear?

101. If you could take us anywhere in the world right now, where would you take us?

102. What is your biggest regret?

103. If you died tomorrow, what would you wish you had done?

104. Can you pin point the moment in your life where you were the happiest?

105. What song makes you unconditionally sad?

106. If past lives are real, what was yours?

107. Have you ever seen something you can’t explain?

108. What is your biggest accomplishment?

109. If you could do one thing without suffering the consequences, what would
you do?

110. What is the strangest dream you’ve ever had?

Questions To Ask If You’re Ready To Know Dig Even Deeper

111. What is the darkest thought you’ve ever had? What about the darkest thing you’ve never told anybody?

112. Is there something out there, a thought, an idea, a current event, or a fear that you find deeply unsettling?

113. What would you consider to be your deepest fear? (This question can be really telling of the depth or lack thereof of a person.)

114. Is there an activity that calms you? A place or a thing that makes you feel at ease?

115. What makes you feel uneasy? Overwhelmed? Anxious?

116. What is your favorite song and why?

117. Do you have a favorite book? A line in a piece of literature? A poem? Why do you relate to it?

118. What scene in a movie has evoked the most feelings out of you?

119. What do you do or where do you go when you need to be alone?

120. What makes you feel like you need to be alone?

121. Can you remember a time in your life you felt the most alive? Tell me everything about that memory.

122. When have you felt the lowest in your life?

123. Where have you felt the most failure? The most success?

124. Tell me about the facts or harsh truths you choose to ignore but know you shouldn’t.

125. When have you felt like you were living life to the fullest? When have you felt like you weren’t?

126. What is the first lie you ever told? Which is the biggest?

127. What is the first secret you ever kept from anybody? Which is the biggest?

128. Are you a religious or spiritual person? Tell me why and tell me how.

129. Have you always had the same political beliefs? Is there something that impacted them?

130. Where do you find meaning in your life?

131. Have you ever been in love? Tell me about the times you have been.

132. Tell me about the times someone broke your heart.

133. Why did you cry the last time you did so?

134. Have you ever cried tears of joy?

135. What did you do when you hurt someone the most?

136. If your life was a movie or a book what would be the title to it?

137. When have you caused the most harm to yourself?

138. What has been the biggest change you ever made that made you the most proud of yourself?

139. Think about the people you love the most in your life, what do you do for them?

140. Is home for you a place or a feeling? Describe that place or describe that feeling.

141. If you could be anywhere other than where you are right now, where would you be and what would you be looking at?

142. Have you ever questioned your sanity and why?

143. What is your most cherished childhood memory?

144. Have you ever had dreams about a past life?

145. Do you have any recurring dreams or nightmares?

146. Do you believe more in fate or that we are the creators of our own destinies because we are governed by free will?

147. Do you believe in extraterrestrial life? Elaborate on why or why not.

148. Would you find more comfort in the theoretical idea that that we were the most advanced species in outer space or would you find more comfort in the idea that we weren’t?

149. What would be your thought process if you were presented with irrefutable evidence that a god didn’t exist? What would be your thought process if you were presented with irrefutable evidence that a god
did exist?

150. What do you think was there before the universe came into creation?

151. Do you believe in other dimensions and parallel universes?

152. How do you define art?

153. If you could have the option of eradicating pain from your life would you choose to do so? Why or why not?

154. Is a life exclusive to pleasure (no suffering) worthwhile?

155. What do you think happens after death, if anything?

156. If you could be given the date of your death would you want to know it?

157. Presented with the opportunity to be immortal would you take it?

158. Would you rather be loved or love?

159. How do you define beauty?

160. Where does happiness come from? Define what happiness means to you.

161. Do you believe yourself to be truly free? If so, why? If not, what is holding you back?

162. Deja-vu: is there anything to it or merely coincidence?

Unconventional Questions That Will Help You Get To Know Someone

163. What was your father or mother like at home? How does he or she act different outside of family?

164. If you were given a choice to choose your manner of death, how would you die?

165. Tell me a really, really stupid joke that made you laugh.

166. Pick two out of physical chemistry, lifestyle compatibility, emotional compatibility and intellectual compatibility.

167. If you were forced to vote for one the biggest dictators of history, (Hitler, Mussolini, Mugabe, Mao, Saddam or Stalin), which one would you pick and why?

168. Show me a music track or a scene from a film that made you tear up.

169. If you could have any animal in the world as a pet, what would it be and why?

170. If you were given a chance to explore the oceans, go to outer space or visit 50 different countries, which one you choose and why?

171. Do you think that men are more rational and women are more emotional?

172. Out of the negative emotions of greed, anger, jealousy and hate, which one would you say affects you the most?

173. Out of the positive emotions of compassion, positivity, enthusiasm and initiative, which one is your biggest strength?

174. If you could be President of your country for an hour, what is the one thing that you would change?

175. Describe your best first kiss.

176. Has another’s pain ever given you joy? Be totally honest.

177. Tell me your biggest strength outside of your workplace.

178. If you were given a choice to turn into a zombie or to die, which would you pick?

179. If you had to pick one, what is the most important value you would teach your children? Honesty, Kindness or Courage?

180. Are you health conscious?

181. Name the one bad quality you wouldn’t mind in a partner.

182. Name the one worst quality you cannot tolerate in a partner.

183. Tell me your biggest supernatural or paranormal fear?

184. If you got a free cheque for $5,000 right this second, how would you use it?

185. Name one really surprising thing that set your heart pumping and gave you an adrenaline rush.

186. Tell me about the time you were so embarrassed in love, you wished you could disappear right there and then.

187. Have you ever been unable to sleep? What do you do with your time then?

188. Tell me about your biggest love regret that made you wish you could turn back time?

189. Do you believe in materialism or spirituality?

190. If you were forced to pick one religion on this planet, which one would it be and why?

191. What is the most romantic and loving thing you have ever done for somebody?

192. What is the most adventurous thing you have ever done in your life?

193. What’s your day-to-day mantra?

194. What quote resonates with you more than any other?

195. What’s your anti-motto?

196. What trait do you envy in others?

197. What skill do you wish you had?

198. How do you wish to be remembered?

199. How would your best friend describe you in five words?

200. How would you summarize your life purpose? Thought Catalog Logo Mark


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Too often we get swept up in the chaos and stress of everyday life. Many people get stuck in the monotony of work, eat, sleep and repeat. This routine can make it difficult to have an insightful conversation with your significant other.

Whether you and your love are sharing a quick meal or cuddling before bed, you can use that time to connect on a deeper level. It’s important to take advantage of the little moments throughout the day. We’ve put together a list of 116 deep questions that will spark fun and meaningful discussions.

Just download and print the questions. Then, put them in a jar or attach them with a ring. We’ve added blank pages so that you can write your own, too!

Deep Questions About Childhood

deep childhood questions

  1. What is your best childhood memory?
  2. What is your worst childhood memory?
  3. What was your biggest fear as a child?
  4. What was your favorite year of school?
  5. What was your favorite subject/class in school?
  6. What did you want to be when you grew up?
  7. What was your favorite game to play?
  8. What is the single most important thing you learned as a child?
  9. What is your most memorable family event?
  10. What do you admire most about your parents?
  11. What do you look forward to about being a parent?
  12. If you don’t want to be a parent, why?
  13. Do you want to live near or far from relatives?
  14. When your parents get old, how do you plan on taking care of them?

Deep Questions About Love

  1. When was the first time you said “I love you” to someone in your life other than family?
  2. When and where did you go on your first date ever?
  3. Do you remember our first date?
  4. Were you nervous during our first kiss?
  5. When did you know you loved me?
  6. What is your ideal night?
  7. What is your favorite thing about me?
  8. Do you believe in true love or love at first sight?
  9. Do you think people are made for each other?
  10. Where is the perfect honeymoon locale?
  11. Describe a fun date that only costs $20.
  12. Describe the most romantic date you can think of — spare no expense!
  13. If you were on a dating game show, what questions would you ask?
  14. What is your favorite memory with me?
  15. What do you look forward to experiencing with me?
  16. Would you rather a night in a fancy penthouse suite or a private beach house?

Deep Questions About Values

deep questions about values

  1. Would you rather acquire material items or experiences?
  2. If it cost the same, would you live in a mansion or a mid-sized house with a lot of land?
  3. In what scenario, if any, is it okay to lie?
  4. When, if ever, is it okay to break the law?
  5. What is the most important lesson to teach a child?
  6. How often do you go out of your way to help someone?
  7. If you could pick a new “golden rule,” what would it be?
  8. What are important societal values? (ex. Democracy, fundamental rights, etc.)
  9. How have your values changed from ten years ago?
  10. What do you see as your best character trait?
  11. If you could change one thing about your character, what would it be?
  12. Would you consider yourself a pessimist or an optimist?
  13. When were you the most disappointed in yourself?
  14. When were you the most proud of yourself?
  15. Generally speaking, do you like the way you look?
  16. If you could change one thing about the way you look, what would it be?
  17. Do you put as much effort and emphasis on inner beauty as outer beauty?

Deep Questions About Goals and Motivations

  1. Who in your family do you view as a role model?
  2. Are you inspired by any celebrities dead or alive?
  3. What thought or object gets you through the day?
  4. Do you find praise or criticism to be more motivating?
  5. What inspires you to better yourself?
  6. What advice would you give to your children to stay determined?
  7. What is the best way to motivate each other?
  8. What is your greatest success to date?
  9. What do you hope to achieve in the short-term?
  10. What is your long-term goal?
  11. What is your biggest regret?
  12. What mistake did you learn the most from?
  13. What are you most ashamed of?
  14. Is failing less, equal or more important than succeeding?

Deep Questions About Relationships

deep relationship questions

  1. What do you look for in a friendship?
  2. What is/was your longest lasting friendship and how did it last so long?
  3. Do you think you can have multiple best friends or only one?
  4. Do you think your pet can also be your friend?
  5. Do you consider your parents as friends?
  6. Do you think opposite genders can maintain a friendship without developing a love interest?
  7. What is an unforgivable action?
  8. What is your advice for long-distance friendships?
  9. Do you have different advice for nearby relationships?
  10. In your opinion, can long-distance relationships survive?
  11. Do you think a couple should split costs?
  12. Do you think it’s better to save money or invest?
  13. How should household chores be divided?
  14. What do you look for in a significant other?
  15. What is the most important thing in a relationship? (e.g. trust, respect, etc.)
  16. How often should a couple argue or fight to maintain a healthy relationship?

Deep Questions About Life Events

deep life event questions

  1. What was your best birthday?
  2. If you could only celebrate one holiday each year, what would it be?
  3. Do you prefer family events or alone time?
  4. Provided there is good weather, do you enjoy indoor or outdoor activities?
  5. What is your ideal wedding ceremony?
  6. Describe your perfect vacation.
  7. What is the best concert you’ve ever attended?
  8. What events are on your bucket list? (ex. Lollapalooza, Macy’s Thanksgiving Day Parade, etc.)
  9. When, where, and how long was the best road trip you’ve ever taken?
  10. Would you rather spend a week in New York City or Los Angeles?
  11. Have you ever been camping? What was your favorite part?

Deep Questions About Stress

  1. Is there anything that gives you overwhelming anxiety?
  2. How do you handle high-stress situations?
  3. What is the most stress-inducing thing that could happen at work?
  4. What helps you decompress?
  5. Is there a smell that instantly relaxes you?
  6. After a horrible day, would you prefer a nice dinner out or a cozy movie night?
  7. Are you terrified of anything fictional? For example, the supernatural or zombies.
  8. What is your biggest fear in life?
  9. Do you have any phobias?
  10. Do you have any irrational fears?
  11. What was the worst nightmare of your life?
  12. Do you like to pull scary pranks on people?
  13. What is the scariest movie you’ve ever seen?

Deep Hypothetical Questions

deep hypothetical questions

  1. If you could have one superpower, what would it be?
  2. Do you think flying or mind reading is a more functional power?
  3. If you could have one human talent that you don’t currently have, what would it be?
  4. If you had three wishes, what would you wish for? (excluding more wishes)
  5. If you had the power to correct one problem in the world, what would you fix?
  6. Where would you go if you could teleport anywhere in the world?
  7. If you could be an animal for a week, what would you be?
  8. If you could be an object for a day, what would you be?
  9. What would you do if you won the lottery tomorrow?
  10. If you could eat anything you wanted right now, what would you order?
  11. You’re going to outer space — what planet do you want to see?
  12. If the world ended tomorrow, what would you do on your last day?
  13. Would you rather go back in time to see the dinosaurs or jump forward a thousand years to see our futuristic society?
  14. If you could make one book or movie a reality, which would you choose?
  15. If you could be a character from a hit television show, who would you pick?


There’s no limit when it comes to deep questions to ask your partner. They will often lead to thought-provoking conversations that can tighten your bond. Spruce it up by trying to guess each other’s answers! Pair these conversation starters with a romantic gift or journal, so you can document any surprising things you find out about your partner.

You can also use games to understand your significant other more profoundly. By playing games such as “Desert Island” you might discover something new — learning the three things someone can’t live without is a window into their core personality.

No matter your relationship status, asking deep questions will help you strengthen your romance and companionship.


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