Personal questions are great to get a little more personal and develop a stronger bond with someone.

We’ve successfully covered many things about questions before, but this time I’ve compiled questions to ask someone when you want to really know more about them.

Bring these up with strangers and you’ll deepen your connection. So, let’s start.

84 Revealing Personal Insight Questions (Know Them Better)


7 Best Personal Questions To Ask Anyone

The best questions are ones that can be asked in any conversation. Luckily we've picked out 7 of our best deep questions for you to keep at arm's reach.

1. When you do something positive or helpful to others, do you prefer private recognition or public praise?

Do you want people to know how awesome you are or would a simple "thank you" suffice? Ask for an example of their proudest accomplishment to get a better picture.

2. What are your guilty pleasures?

Reality TV has become a guilty pleasure for most people. And it's common for them to get embarrassed about whatever their thing is. Funny enough, most of the time it's not even the craziest thing about them. Reassure the person answering when this happens that they shouldn't be ashamed of their favorite thing.

3. Upon dying, if you had the choice to re-live your life or live a different life, which would you choose?

This line of questioning can sometimes be hard for some people to confront. It may say a lot about how they believe they've lived so far.

4. Do you ever feel like you would have been a better person if you never met someone in your life?

Whatever the story may be, there's bound to have been personal growth. Ask them about this personal relationship if they're willing to share more.

5. Are you more likely to avoid conflict or engage it head-on?

It's good to know how to handle confrontation, and this may give you an insight into a personality trait about how they cope with conflict.

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6. Do you prefer that people shoot straight with you or temper their words?

Brutal honesty or a white lie? Which is better? Shooting straight is important to be a good communicator but some people prefer the softer touch. This can determine their core character.

7. If you could eliminate one weakness or limitation in your life, what would it be?

You know it's good questioning when it makes someone think deeply about the answer. This may sound like a simple question, but it has so much depth. We all have something we feel holds us back. Perspective always helps.

6 Personal Conversation Starters

Conversation starters can be personal. Depending on the person you're talking to and the nature of the discussion, they may welcome these interpersonal conversation starters. They're excellent to use as icebreaker questions too.

8. How have your friends influenced your personality?

The inside jokes and experiences made with friends helped shape you into who you are today. Don't just limit the talk about current friends either; include a past relationship.

9. How’d you meet your best friend?

Friendship is truly a wonderful thing. A best friend feels like a family member you've chosen for yourself. And people love to talk about how they met their favorite person. Bringing them back to the beginning of what started it all.

10. If you had a free plane ticket, where would you like to go?

Aruba, Jamaica, oooh, I wanna take ya. Reminisce about a favorite holiday you've taken when you were a kid. Memories are also a great topic, one that can stem from talking about travel.

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11. Aside from the job you have now, what sort of work would you like to do?

What's your passion? or similar questions are good as lead-ins for discussing future hopes and dreams.

12. What’s the best part of your daily routine?

Is it a particular caffeinated beverage in your cup? It's interesting to know what people enjoy and love the most about their day. Usually, it's the smallest of things that make the most significant difference.

13. What is something that you know a lot about?

This can open a window into people's lives. Some can, and will, talk about their hobbies and what they love for hours if you let them. You can learn a lot about what someone has invested a lot of time and effort into.

6 Get To Know You Conversation Topics To Talk About

When you want to get to know someone you have to ask get to know you questions. And there's no better way to get to know someone than asking personal get-to-know-you questions!

14. What do you keep under your bed?

Haven't you gotten rid of your scab collection from Elementary school? Do you have items of sentimental value from an old boyfriend? It's not always just monsters under people's beds.

15. Have you ever won an award?

Something as simple as a 3rd place trophy in the Pinewood Derby or as impressive as the Mark Twain Award.

16. Are you currently happy with your personal life?

Often reaching for a seemingly impossible goal can be someone's biggest fear and without achieving it, they won't feel accomplished. Or maybe their biggest regret is holding them back from being truly happy.

17. Which of your possessions could you not live without?

Is your phone really your lifeline in the modern world? You'd be surprised how many ways people can answer this if the conversation is good enough.

18. When was the last time you cried? Why?

Did you know crying releases endorphins? That's why it's completely healthy to cry. Was it a movie or an experience that caused the tears? A good book? We all experience different moments of grief or frustration. But sometimes we cry when we're happy. Share these moments.

19. What is the one thing that you feel you can never outgrow?

What makes you feel young again? This can turn boring small talk into something exciting where your answers may have you digging up boxes for some old games and toys. Perhaps a pair of rollerskates?

7 Personal Things To Talk About With A Girl

When you're talking to a girl, whether you like her or not, you should always have a slew of questions to ask a girl. And you can always pepper your conversation with personal questions to ask a girl.

20. What foundations need to be in place for a relationship to be successful?

First, you need to discuss what defines a successful relationship as this differs from person to person. Then lay out your ideas of the foundations that build them. Having these discussions are sure to improve your relationship.

21. What are your healthy and unhealthy habits?

While it's okay to indulge, balance is critical when it comes to habits. Depending on what it is, it can have a significant impact on your health and wellbeing. It can also affect relationships or cause financial strains. Talk habits that go beyond biting your nails. You might find things in common that you can work on together too.

22. How was your life growing up?

Unless you grew up together, chances are you don't know much about their childhood. Learning about her life growing will help you understand her more.

23. Where do you find inspiration?

Inspiration can come from anywhere and when it does, wonderful things can happen.

24. What incident changed your life instantly?

People's lives can be a complicated mess. And sometimes along the way something happens that completely alters it. If you're looking to know more about her life, ask this. Some of us have experienced life-changing events and have remarkable stories to tell. Good or bad, it's healthy to talk about them.

25. Why did you put an end to your last relationship?

If you like her, be sure not to make the same mistakes as the last guy. But simply knowing the answer will be sure to bring you closer together.

26. If I proved to you that you were dreaming right now, would you want to wake up?

This is one way to tell if a date is going south. It's also fun to ask.

6 Personal Inquiries To Ask Guys

Guys often build relationships a little differently. Most open up slower and aren't natural talkers. But that's more the reason why you should always have some questions to ask a guy handy.

27. Have you ever cheated on someone or helped someone else cheat?

No one begins a relationship expecting they'll cheat on their partners. This may be tough for them to answer, but reassure them it's judgment-free. Remember, you're asking these questions to get to know them on a deeper level, not to judge. Do they believe there is happiness in polygamy?

28. What are some buy-it-for-life items you own?

A belt with a lifetime guarantee? A backpack made to last? Sometimes it's worth it to spend a little extra.

29. Should the man always pay for dinner?

The question of who should handle the bill is one that's been around for a long time. If he believes he should always pay for dinner, dig more. Does he believe this to be chivalrous? Or romantic? Does he have other advice or ideas on how to surprise each other in a relationship?

30. How do you stay healthy? What's your workout routine and diet?

As fitness can lead to better cognitive thinking and also cultivates self-discipline, talking health is important! Some guys can offer the best tips when it comes to health and fitness. Diet fads aren't great and if you're asking the right person, you might just find motivation for a healthier lifestyle.

31. What actions define a man?

It's what you should constantly strive for. A classic debate can ensue with this one.

32. Would you rather get married, or is it too much of a hassle?

People have their personal opinions of marriage. Whether they're ready to settle down, something they see in their future, or it's something they'll try to avoid at all costs, marriage is a personal topic that's intriguing to ask about.

7 Questions To Ask Your Friends That Are Personal

Maybe you want to become even closer to a friend of yours. Our list of questions to ask friends is a great resource, but here are some personal questions to ask your friends for a more intimate encounter. And it's more than just asking what their favorite song or favorite book is.

33. How do you behave around colleagues?

Some people tone it down at work. It's a good question to ask about their work-life.

34. How much do you want to achieve in your life?

Maybe you can help. That's what friends are for after all.

35. Have you ever experienced something you couldn't explain?

A missing hoodie or a ghostly apparition? Life is full of the unexplainable.

36. What would you do with $1,000,000?

There is so much they could do and it could really change their life. Would they blow it all in one go?

37. Do you ever feel held back by your status or background in life?

What happened in the past is in the past. You make your future.

38. Do you stay in touch with people forever or maintain distance when they are not part of our life anymore?

Dunbar's number is an interesting theory to look into.

39. What do you think about your first impression on people?

How do you want people to see you?

8 First Date Questions To Ask To Get To Know Them Better

One of the most important times to have prepared questions is on a first date. Start off with general first date questions and move into more personal territory with the following deep questions.

40. What is your favorite little-known place in your city?

It's important to be a tourist in your own town from time to time. You'll become an ambassador of sorts and find some hidden gems.

41. Where do you want your home to be when it's time to settle down?

Some people never settle and that's okay too. Everyone has a different plan for their life, but knowing a person's ideal location can say a lot about them.

42. What roles should each party have in a romantic relationship?

A relationship takes a little bit from both parties. How do you keep one together?

43. What was the best birthday of our life and why?

We threw a surprise party for my friend once. We printed out many pictures of his face, and everyone sat in the dark with them strapped to their faces until he got home. He was pretty surprised.

44. How can I instantly put a smile on your face?

Make people smile, make the world a brighter place.

45. What are the three most important things in your life?

What do you cherish every single day? You can even say these are the things in your life that you can't live without.

46. What’s your favorite vacation spot?

Travel is essential to becoming a more grounded individual. Doing it solo is even better than in a group too. No matter where you find yourself, there's always that one vacation spot that your mind always wanders to.

47. What was your first impression of me?

Bad first impressions can be mistaken but it's best to avoid them in the first place.

6 Something To Laugh About Your Personal Life

Everyone has a love for laughter so be sure always to have a few funny questions to ask. Of course, funny questions can be personal too!

48. What’s the worst thing a person can do that isn’t illegal?

How can you leave the most emotional scars on someone?

49. When was the last time you screamed at the top of your lungs?

Why not do it right now? The looks you'll get will make for a great memory.

50. What is the worst thing that somebody has walked in on you doing?

It happens and it's always awkward for everyone involved.

51. What is the weirdest nickname people call you?

My friends call me Kaaaaarrrrl because of that Llama that goes mad in those YouTube videos.

52. What's the most personal question you have ever answered?

Hopefully, it's not this one. If so, make sure to go through this entire list with them.

53. How difficult is it for you to be honest, even when your words may be hurtful or unpopular?

Honesty is the best policy but it's not always easy to maintain. Sometimes, it's the truth that can bring us wounds. That's why some people keep up their lies even when it's too much.

5 Interesting Yet Personal Things To Ask

If you're going to get personal with someone, you can't just ask the same boring questions they've heard a million times. Instead, ask interesting questions that allow them to show their most interesting—and personal—side.

54. Do you think someone is better than you at your job?

This shows how much awareness, humility, and honesty the answerer has. It can also introduce a topic of discussion about their workplace and their work experience.

55. Is it easy for you to show yourself love or speak kindly to yourself?

What kind of self-love do they practice? Do they do morning affirmations? An interesting question that people are never asked, for some reason.

56. What do you want people to feel when they’re around you?

A roundabout way of asking a fundamental question: who do you think people think you are?

57. Do you think your parents did a great job raising you?

Parents, childhood, and an evaluation of themselves in the present can have you engrossed in this topic for hours. Enjoy it with siblings and see if you have different opinions.

58. Do you believe in Karma as “what goes around comes around”?

The answer always impacts how someone sees the world. More profound talks are a fascinating way to get an insight into how a person thinks.

7 Would You Rather Questions That Tests Your Personal Preferences

Sometimes, the best way to get personal is indirect, through fun, silly games. You can use would you rather questions to get beyond surface-level chat and really dig into the personal stuff.

59. Would you rather die young or live until you're old?

Answers usually depend on how old the person is. But people do value their lives differently. Some fear old age; some embrace it with open arms.

60. Would you rather end hunger or hatred?

This leads to some very deep, philosophical conversations about the nature and sources of hunger and hatred. It's like talking about world peace, only different.

61. Would you rather be happy or be rich?

Is it possible to be both? When you ask questions like these, try to debate their answers for a more in-depth exchange. How do they define happiness?

62. Would you rather be without eyes or a mouth?

Imagining life with either scenario is challenging. You can ask a million and one of these "would you rather" questions and keep the discussion rolling.

63. Would you rather find out that there’s God just like the Bible says or find out there’s no God out there?

A theological line of questioning, we've all asked ourselves this—alone—at some point. Share your answers now.

64. Would you rather be poor and work at a job you love, or rich and work at a job you hate?

Also known as "millennial's choice." Talk about what aspects of their current job they like? Then branch out about whether it was something they wanted to get into or was it by accident.

65. Would you rather they find the real cause of your death or miss it and make you a famous case?

A great question to consider is our cultural obsession with fame. There are so many unsolved cases out there, some have become household names.

7 Weird Topics To Dig Into

Getting personal is uncomfortable for most people, but you can make that easier by digging in with these weird questions to ask. People feel a little more comfortable opening up when you go weird because there's usually less tension.

66. Do you pluck or shave or wax your underarms?

A grooming tip discussion that often comes with a laugh. Everyone's habits are different and sometimes it's fun to discover.

67. Was there ever a time you literally thought out loud?

Have them act it out to make it extra fun and extra personal. Was it in public and did anyone notice? Embarrassing moments are also fun to talk about.

68. Do you pray before sleeping?

This is a weird—but effective—indirect way to get into a discussion about God and religion.

69. How many hours of sleep do you usually get?

We could all use more, but how much are they missing out on? And why? There is so much research out there on sleep hygiene, exchanging tips for a better night's sleep is always appreciated.

70. Do you think astrology is crazy or accurate?

Astrology always brings up a lot of passionate debate. Which side are they on? You can then see if your astrological signs match.

71. How do you approach a person who is known for his difficult attitude?

This tells about their personality and is a great way to pick up tips for your next encounter with Mr. Difficult. Perhaps you may end up discussing the same person and share some stories on frustrating encounters.

72. What’s the most surprising self-realization you’ve had?

Hit them with this after a few other weird ones to really get personal. Some people don't know too much about themselves until questions are asked that have them reflecting.

7 Curious Questions To Ask A New Friend That Are A Little Bit Personal

CultureEven if you've just met your friend, you shouldn't be afraid to ask some personal insight questions as long as they're willing to answer. If you're looking for the right not too intrusive questions to ask a new friend then you're in the right place.

73. Do you have any fears?

Don't take it personally if they don't want to answer. Some people are afraid their fears can be used against them.

74. What do you like most about your family?

The things we like most about our family can manifest themselves in how we are as people. If their family members are considered unusual, there are usually some fun stories to be told.

75. Who was your role model growing up?

It's interesting to know who helped them be the way they are. Real or made-up characters, who were the bigger big influencers?

76. What keeps you up at night?

It's the thoughts that keep us up at night that mean the most to us. Sometimes it's overthinking, or simply endlessly planning for the day ahead. Whatever it is, burdens shared have less weight.

77. What do you think is the worst way to die?

It's something that's slow and painful, probably.

78. What is your love language?

It's important to know someone's love language even if you're just starting out as friends. You'll learn how to better communicate and appreciate each other.

79. What habit are you trying to quit?

Breaking a habit can be difficult. Maybe you can help give them that extra push.

5 Personal Things To Ask Your Crush

You want your relationship with your crush to be as deep as possible. You want to know more about them. That's why you should know the right questions to ask your crush. Those that will lead you to a deeper level of understanding with them.

80. What’s your greatest fear?

It's natural to be scared of something. Sometimes they are irrational fears that make us self-conscious. When you think of questions, this one is pretty common. But you can dig deep about this with her. Does she know the possible causes of her fear? Is there a story to tell where the fear took over?

81. What’s something you find attractive that most people don’t?

The weirder the answer, the better. Sometimes, we don't need to cave in to society's standards. You'll know more about what she likes and what attracts her. Take notes!

82. If you have a free day, how do you usually spend it?

People basking in their element always paints a different picture for each individual. It's refreshing to have a free day when you don't have to succumb to your daily routine. You'll know more about her from her answer to this question.

83. What’s the one thing that drives you crazy about other people?

Some people just have that habit or thing about them that can drive you nuts. And you don't even know why!

84. If you could have one superpower for a day, what would it be?

The list of superpowers is endless. The more creative answer she can come up with, the more fun.

Downloadable and Printable List of Personal Questions

Here is a downloadable and printable list of personal questions (right-click the image and select Save Image As...):

How to Ask Personal Questions

Are there rules for asking these kinds of questions? Societal norms say yes! So be sure to keep these steps in mind when asking.

1. Don't start with intrusive questions

Getting too personal too quickly can drive some people away so it's best to ease into these questions while you're on the subject.

2. Share your own experiences

If you're only asking questions and not providing details about yourself, you're an interviewer.

3. Respect Boundaries

Recognize when they look uncomfortable by the questions you're asking and back off when necessary. If you can't tell, just ask!

Frequently Asked Questions

Still unsure what the right question is? All of these may have triggered some questions of your own, so check out our FAQs for answers.

How do you know if a question is already too personal to ask?

It's all about reading the recipient. Body language and facial gestures should really tell if they feel you've asked uncomfortable questions.

What should I do to make the conversation less awkward?

How to talk to girls or guys without awkwardness is to avoid the awkward silence that sometimes comes up when there is a lack of things to say. That's why it's handy to have questions already in mind. Ask an appropriate question but make sure to be an active listener too. Exchanges can become awkward when one person isn't really listening.

How do I make her enjoy our small talk?

Remember, it shouldn't feel like a job interview. Making it entertaining is how to keep a conversation going with a girl. If you want her to enjoy the small talk, make sure it's interesting. Ask open-ended questions, maintain eye contact, and smile. Most of all, make sure to lose the phone!

What things should I never ask a girl?

Never ask anything about her weight or appearance unless it's leading to a genuine compliment. A huge, definitely do not ask the question, "Are you pregnant?" If you're unsure what to say to a girl, read more of our articles to help you.

More Great Questions To Ask

When personal questions become tedious, you can always mix things up. Try some of these great questions to ask for a successful chat with anyone.

  1. Ever run out of things to talk about? That won't happen anymore if you have some conversation topics on hand.
  2. Fun questions to ask are great for having a... well... fun discussion.
  3. You can always learn something new about your romantic partner. Our questions for couples will keep things romantic, fiery, and enjoyable.

In Conclusion

When you want to turn an acquaintance into a friend or simply want to know more about them, personal questions are some of the best questions to ask.

So get out there and get personal.