If you really want to get to know someone inside out, you need to ask the right questions. No matter if you’re dating, meeting new people, or connecting with your co-workers, it’s always helpful to have a couple of deep questions at hand that aid you in getting to know the person you are talking to. However, asking the right questions that make others reveal (intimate) details about themselves is an art in itself. In the following, we’ve created a selection of those ingenious questions that get others talking about themselves without an end. Enjoy this collection of good questions to ask if you really want to get to know someone.

Let’s face it, we’ve all been confronted with situations in which we really wanted to get to know someone but had no idea how. We’ve all sat in front of someone we found interesting but did not know how to break the ice.

These situations can be quite awkward. In fact, you’re confronted with quite a dilemma. On one hand, there is this person you really would like to learn more about. Perhaps it’s even a person that you find interesting. On the other hand, good questions escape you. To be precise, you don’t even know how to get the conversation going.

“If they can get you asking the wrong questions, they don’t have to worry about answers.”
Thomas Pynchon

What could be worse than being in the company of an interesting person without having any idea what to talk about? What could be more uncomfortable than being stuck in a conversation that barely scratches the surface?

Luckily, it doesn’t have to be this way. Here’s our collection of excellent questions you can ask the people you want to get to know.

100 Good Questions to Ask to Get to Know Someone

Skilled communicators know that the right question at the right time can work wonders. An interesting question can help you to get the conversation started but can also aid you in getting the other person to open up. Even more so, asking engaging questions is an essential key of many effective communication techniques.

The following questions in themselves are already quite powerful. But how can you make the best use of the following list? Here are a couple of important tips that help you to keep the conversation going.

Don’t ask one question after the other. Allow the conversation to develop. Give your counterpart enough time to answer the question. It’s not about how many questions you ask!

Don’t switch from one subject to another. Remind yourself that it’s not a job interview where you quickly switch from one topic to the next one. Allow the subject to unfold naturally.

Show real interest. If you’re really interested about one subject, your counterpart will notice.

Ask follow-up questions. You can avoid switching from one subject to another by asking engaging follow-up questions.

Emphasize. Nobody likes talking to people who “know it all” or ridicule one for mistakes. Whenever the conversation touches sensible areas, try to show compassion.

In the following, you can find 100 excellent questions that help you to have interesting conversations, which allow you to build deep connections with those around you.

Here are the thought-provoking and interesting questions:

1. What would you do if you could live forever?

Let’s start with a really thought-provoking question!

By asking this particular question, you can uncover many interesting aspects about the personality of the person you’re talking to. Firstly, the person will tell you what they would do if they had unlimited time. The answer to this question will give you some neat insights about this person’s preferred spare time activities. Secondly, your discussion partner will show you how they would behave in a situation in which having to work is no longer a must.

Interestingly enough, many will tell you that they would relax, chill out, and sleep for years. Others may tell you that they would continue working in the profession they already like.

After some time, however, your discussion partner will start thinking. That’s the point where they really begin to think deeply. Listen closely to the answer.

2. What would your first decision be if you were elected president?

Let’s continue with another engaging question. This particular one will give you some nice insights about the most important (personal or political) issues this person is either confronted with or wishes to be solved. It can be quite interesting to see that some would immediately address a problem only they are confronted with, while others manage to keep the bigger picture in mind.

At the same time, this is a good question to indirectly ask what political party they favor.

3. What items would you take to a lonely island if you could only take four things?

Never mind asking a person if they are truly addicted to something. They won’t tell you. But thanks to this ingenious question, you will quickly find out what four items this person cannot live without. Are you talking to a person that is addicted to their cell phone or someone who can’t stop watching TV? Ask this question and you’ll see what exactly matters most to them.

4. If you had a “get out of jail free” card, what crime would you commit?

This deep question will introduce you to the darker side of the person you are talking to. Interestingly enough, there is almost no person that will simply tell you that they won’t make use of this card. Instead, most will not only tell you what crime they would commit but also the particular reason why they would do such an act. At this point, make sure to dig deeper and find out why they have chosen especially this criminal act.

5. What book or movie has had the greatest influence on your life?

We all have this one particular book or movie that greatly shaped who we are. By making use of this question, you will gain some very interesting insights about the personality of the person you’re talking to. Not only will you discover what kind of genres the other person likes most but also what work of fiction left a considerable mark on them.

6. As a kid, what did you want to be when you grew up?

Isn’t it interesting to not only ask someone what they wanted to be as a child but to also see whether or not they have managed to realize their dream?

7. What would you give your life for?

Admittedly, this is not a particularly lighthearted question. At the same time, it can prove to be tremendously insightful.

It’s fairly safe to say that most of us don’t want to leave this planet in the near future. Still, many have asked themselves if they are willing to give their life for a good cause. Find out for what particular cause the other person is willing to give their life.

8. If you could be the character of a movie, TV show or book, which one would you be and why?

This particular question will get your discussion partner thinking. And let’s be honest, isn’t it absolutely thought-provoking to imagine you could be living in the imaginary world of your favorite book or movie?

At the same time, the answer to this question will tell you many things about this person’s identity. In almost all cases, they will choose a character that is very similar to themselves – a person they highly identify with.

9. If you could travel back in time, where would you go?

Admittedly, this is a sneaky question to find out whether or not your conversation partner is historically interested. The more superficial the answer, the less interested in historical events they are. If you want to dig deeper, ask them about the specific event they would like to witness.

10. Let’s assume you’d win the lottery tomorrow. What would you do?

No one will tell you whether or not they are pretty self-centered, selfish, and materialistic. But by asking someone what they’d do if they’d win the lottery, you can quickly find out.

Astonishingly, many people will share really interesting ideas with you. Yes, there are some who really have no better idea but to spend all the money for themselves. But most other people have brilliant ideas how not only they themselves can live a better life but also how they could make this world a better place.

11. What do you want your legacy to be?

Each and every one of us wants to be remembered for something great. By asking this question, you will discover what it is that it motivates the other person to get up each morning. At the same time, you will find out what exactly your discussion partner wants to leave behind.

12. If you could change one aspect about the past, what would it be?

Imagine someone asks you whether or not you are happy with how things are. Wouldn’t you think that this is a really boring starter of a conversation? Instead, ask them what they would change about the past and you will quickly find out if they like how things are in the present.

13. Would you change history if you could?

With great power comes a lot of responsibility – this question helps you to uncover if the person you’re talking to would use this kind of power wisely.

14. If you could have any superpower, which one would you choose?

The answer to this question may be funny but in the end, it is not that insightful. Therefore, it’s important to follow-up on this question and to ask the other person how exactly they would use this specific superpower. Doing so will help you to gain tremendous insights into the personality of the other person. Would they use their superpower for self-centered purposes or are they choosing something that others could benefit from?

15. Who was your childhood hero?

By asking this particular question, you can find out a lot about this person’s personality as a kid. Make sure to follow up by asking them about their present hero to get a better understanding of their present character.

16. What motivates you to get up in the morning?

We all have something that motivates us to go out and do what we have to do. By asking this good question, you can find out what it is that helps the other person overcome difficulties and challenges in their life.

17. If you could send a message to an alien species, what would it be?

Be prepared for some really funny answers to this good question.

18. What would you do during a zombie apocalypse?

There are some who would hide and others who would fight during such a situation. This question will help you to find out what personality type your discussion partner is. At the same time, you may get some really funny answers.

On a more serious note, the answer will definitely show you if the person you’re talking to is prepared for unexpected disasters in real life.

19. What musical instrument have you always wanted to learn?

This question could lead the both of you into lengthy discussions about all kinds of musical topics, such as favorite songs and favorite musicians.

20. If you could live anywhere, where exactly would it be?

Forget about asking, “Do you like where you live,” or “Do you enjoy living in this country?” These questions will most likely not bring you very far. Instead, ask them where exactly they want to live if they basically could live anywhere. Not only will you find out if the other person likes living where they live but also if they are a city or country person.

21. What’s the best comedy movie you’ve ever seen?

We’ve all seen those movies that made us laugh until we’ve cried. This fantastic question will not only help you to get some pretty good suggestions for your movie watch list but it may also provide great topics of conversation. At the same time, the answer will indicate whether or not you and the other person have a pretty similar sense of humor.

22. If the purge were real, what would you do?

This question has one purpose: to help you find out if you are confronted with a predatory aggressive personality type. Interestingly enough, the people that would either leave the country or go into hiding are quite rare. Most will either choose to defend themselves or do away with some people they dislike.

23. Would you accept a one-way ticket to Mars?

Right as we speak, there are pretty advanced plans to send a group of people to Mars – without a return ticket. You will see, it’s not only a very thought-provoking question but will definitely give you many things to discuss.

24. If you had the chance, would you choose another profession?

Asking someone where they work is a really boring question. In most cases, you will hear, “I work at (company) as a (profession),” and that’s it. If you’re interested in their profession, just ask them if they are happy with their present occupation. They will definitely tell you where they work and in which position – you don’t even have to ask for it directly.

At the same time, by asking this excellent question, you will discover what kind of coping mechanisms the person in front of you uses in order to deal with dissatisfaction. Some are very adaptive, meaning they have learned to tolerate the frustration. Others are more active and aggressive in their approach and will quickly change what they don’t like.

25. What motivated you to choose your profession?

This one is a good follow-up question to #24. At the same time, you can also ask this question as a standalone question when you want to find out what their profession is.

The answer to this good question will give you helpful insights into the main factors that motivate this person. Similarly, it will show you whether this person is highly ambitious or not. Some will be driven to attain status, fame, or riches and plan every step accordingly. Others might have come to their present occupation through a series of (interesting) coincidences.

26. What do you think is more important: exploring the world or yourself?

Basically, the answer to this question will show you if this person is outgoing, curious, and rather extroverted or if they are a little more introverted.

27. Which fictional character would you bring to life?

This one is a particularly telling question. The answer will show you whether your discussion partner would bring a character to life just for the fun of it or if they actually consider choosing a character that could make a difference in the world.

28. Which trend or passing fad would you revive if you could?

There are some trends or temporary fashions that we are really ashamed of. Every once in a while, however, there comes a fad that is simply amazing.

29. What do you prefer, being a true master in one area or proficient in many?

A fantastic way to subtly discover if a person has the potential to be an entrepreneur or a manager is to ask them this question. It will show you whether the other person is more likely to be a specialist and therefore an employee or in a very responsible position as an executive/manager, which requires a generalist.

At the same time, the answer to this question will show you if your discussion partner has the willpower to pursue one skill until they have mastered it or if they skip from one to another.

30. What do you want to be your final words?

I’m a big fan of this question because it shows me whether a person has humor or not. While there are some who would choose really nasty remarks as their final statements on earth, most people would choose totally hilarious words.

31. What law would you change if you could do so?

This is another good question to find out if the person has only their own well-being in mind or if they would make use of this power to make the world a better place.

32. What would be your last meal as a prisoner?

Ask the other person if they would choose their favorite meal or something really extraordinary.

33. Space exploration or ocean exploration: what would you sign up for?

Ask the other person if they would rather explore the depths of the ocean or if they would prefer to explore space. It’s a pretty funny question and can lead to lengthy discussions once you start asking “Why?”

34. What’s the number one thing you would change about yourself if you could?

Instead of plainly asking another person what they absolutely dislike (or even hate) about themselves, make use of this good question! It will also help you to see how confident the other person is and if they are comfortable with who they are.

35. Who was your favorite teacher and why did they inspire you?

I’ve never come across this question during my entire life. But I think it’s quite a nice question to ask. It will give your discussion partner the chance to talk about their childhood and the reason why this particular teacher inspired them greatly.

36. If you could, which musician would you raise from the dead and why this particular one?

Music elicits emotions in every one of us. By asking this engaging question, you can learn a lot about this person’s musical taste. At the same time, the kind of music they are listening to will tell you a lot about the person you’re talking to.

37. Are there inappropriate jokes you can laugh about all day?

We all know those dirty jokes our friends tell us that we could never ever tell most other people. Let’s find out if the person you’re talking to has some great jokes in store. The answer may not only make you laugh but it will also show you what sense of humor the other person has.

38. What do you prefer: city, countryside, woods, beach, or mountains?

Let’s throw in a couple of total opposites and see where this person would rather live.

39. What childhood memory do you hold dearly?

Luckily, so many people have had the great luck of a wonderful childhood. By asking the other person this particular question, you can form a deeper bond with them.

40. What was your best dream ever?

It may not be such a good idea to ask someone about the worst nightmare they ever had unless you are really close friends. But you can always ask the other person about the best dream they’ve ever had. Prepare yourself for some really funny answers.

41. Should one of your friends never ever be elected as president?

You’ll never find out anything by asking the other person whether they have a lot of great friends. So instead, ask them this excellent question, which will help you to learn more about this person’s not so well-behaved friends. But don’t take the answer to seriously. In almost all cases, you’ll definitely hear something great to laugh about.

42. What is it that makes you really happy?

Asking this question is a fantastic way to get your friends and other acquaintances thinking. Usually, people will tell you trifle things in the beginning. They will tell you that listening to music or hanging out with their friends makes them happy. But once you start digging deeper, you will discover some pretty interesting stories.

43. What was your worst failure/setback and what did you learn from it?

The more experienced a person gets, the more likely will they be able to appreciate the positive outcomes of failures. By asking this question, you can find out whether or not the person you’re speaking to reflect on their own life and learns from the lessons life teaches them. You will be amazed by the number of people that repeat one mistake after the other, without ever learning anything.

44. What’s your favorite song and why this particular one?

What do people do with their favorite song? They listen to it all the time. So by asking this excellent question, you can quickly find out in what mood the other person often is. Are they listening to a cheerful and upbeat song or is it a really dark and sad one? The answer will definitely tell you a lot about the other person.

45. Would you make modern technology disappear if you could?

Their answer will show you how they think about technology. And if they have problems with meeting a choice, simply ask them if they would do away with one particular piece of technology if they could.

46. What is your biggest accomplishment and how did you achieve it?

This question is a fantastic invitation for the other person to start talking about their own achievements. Especially when you’re talking to an incredibly successful individual, you will learn many important things by asking them how they managed to become so successful.

47. If you could be a movie director, what kind of a movie would you make?

It can be pretty interesting to ask the other person what kind of a movie they would direct if they had the chance to. You’ll be amazed at the pretty unique answers that you’ll get to this good question.

48. What is the craziest story you’ve ever heard?

Every single person knows a really crazy, shocking, or hilarious story. If you have the opportunity to ask dozens of people this particular question, you will hear some totally incredible stories.

49. What does it take to be a woman/man?

This one is another good question to make the other person reveal a lot about themselves. If you’re talking to a woman, ask her what she defines as a real and true man. Similarly, if you’re talking to a man, ask him what he thinks is a true woman. From my own experience, I know that this question can lead to hours of thought-provoking discussions. However, you don’t particularly want to ask this question your boss or a client/customer of yours.

50. If you could select the TV program for one day, what movies would you choose?

If you are curious about the other person’s favorite movies and TV shows, ask this question.

51. What’s a spectacular or great way to die?

Alternatively, ask the other person how they would like their life to come to an end one day if they could choose.

52. What single thing would you change about the world if you could?

Granted, humanity is confronted with many challenging issues. However, by asking this question, you will encourage the other person to name the number one issue they find most daunting.

53. If you had the chance to telepathically speak to every single human being, what message would you send?

This is not only a thought-provoking question but it may also encourage very long conversations about various topics. At the same time, the answer will clearly show whether or not the person you’re talking to is thoughtful.

54. If you could invent basically anything, what would it be?

The really interesting part about this question is to find out if the other person would invent something only they could benefit from or if it is something that helps millions of people.

55. What’s the number one item you would save from your burning house?

We all have this one item that we simply could not live without. Ask the other person this question, and you’ll very likely find out what material object is of the greatest importance to them.

56. What would you do if you knew that the world was going to end in one week?

This question will provoke some really funny answers. You’ll be amazed at the things people would do in such a situation. At the same time, you’ll also meet people who wouldn’t change a thing about how they live their life, which is quite curious.

57. If someone could give you the answer to any unsolved question, what would you ask?

There are many unsolved questions but with this question, you’ll find out what the person in front of you thinks is the most important one.

58. What important life lessons would you like to pass on to your children and their grandchildren?

Basically, this question will help you to find out if the person you’re talking to is quite experienced in life and if they learned their lessons.

59. What would you never do, even if you were offered $1 million?

There are many things we really don’t want to do. But this huge list may be significantly shortened when someone would offer you $1 million to do it. So ask this question and you’ll be surprised at the things others would not even do for a lot of money.

60. What were the craziest things you’ve ever done?

The answer to this question can be particularly revealing, especially when you’re talking to a really open and adventurous person.

61. What are you grateful for?

The more often you ask this question, the more surprised will you be that many people have never asked themselves this particular question.

62. What important message would you pass onto your younger self?

We all have this particular message that we would like to pass onto our younger selves, if only it were possible.

63. What object have you been searching for years with no luck?

The answer to this question can get really funny.

64. What character traits do you share with your favorite animal?

If you want to learn more about the character of another person, don’t just ask them about their traits. Instead, you can lure them into revealing much about themselves by letting them describe the character traits of their favorite animal.

65. What’s the most ridiculous thing you’ve caught yourself doing in autopilot mode?

Every once in a while, we all catch ourselves doing something really bizarre when we do not pay much attention. Be prepared for some really funny answers.

66. What changed your way of thinking forever?

67. What’s the most chilling story you’ve ever heard?

68. What TV series do you binge watch and why this particular one?

69. What can you do that no one else can?

70. What’s been the best concert you’ve attended?

Ask this question if you don’t only want to get to know the other person but also want to form a bond with them. Specifically, make sure to let them describe all the details about the concert and why this particular live performance was so superb.

71. What’s your favorite language?

Asking someone, “Do you like to travel,” is really boring. Everyone will tell you that they like traveling – even if they hate it. Therefore, it’s time to ask a little more strategically. You’ll be amazed what the answer tells you about the other person. In the first place, you will find out if they’ve come in touch with many different cultures and languages. And if the other person tells you they prefer the language of the country they are living in, they might not like traveling that much, which is perfectly fine.

72. What is it that left you completely speechless?

73. What are the greatest tricks you’ve ever used?

74. Where are you going to be in five or 10 years?

Don’t just ask the other person where they see themselves in five or 10 years. Ask them where exactly they are going to be. Let them describe their personal future in the greatest detail as if it had already happened. Listen closely to the answer, it will reveal this person’s top priority in life. By asking this good question, you will quickly find out whether you are confronted with a career-oriented or a lifestyle-oriented person.

75. What was the most rewarding thing you’ve ever done?

76. What was the scariest movie you’ve ever watched?

77. How are you holding yourself back at the moment?

This particular question is an excellent question to ask your friends and all the other people you have a deep connection with. It’s a pretty introspective question that will encourage the other person to reflect on their life. At the same time, the question may give you the opportunity to provide important feedback and to help them overcome what they are struggling with. In short, it’s an excellent question to deepen a given relationship with a beloved person.

78. Did you ever find a loophole that you exploited?

79. What immoral thing have you done for the right reasons?

80. What does home mean to you?

We all know what a home is and where we live. However, we all may have totally different definitions of what home means to us.

81. What would you make differently in your life if you had the chance?

82. What accomplishment are you most proud of?

83. What was THE defining moment of your life?

84. What memory would you erase if it were possible?

85. How did you get your weirdest scar?

86. What’s the funniest thing you did because you were bored?

87. What did you always wanted to try but never found the courage to do?

88. What’s the weirdest thing you did as a child?

89. What is your most noteworthy talent?

90. What’s your philosophy of life?

91. What is your biggest regret?

92. What do you like more, being a leader or a follower?

Admittedly, this question is not my favorite. But it is an interesting question nonetheless.

93. What profession would you choose if everyone was paid the same?

94. How would you conquer the earth?

95. What is it that you’ve learned way too late life?

96. How do your friends describe you?

This one is a classic question that is used in many job interviews. Basically, the interviewer is asking you to describe yourself from the perspective of your friends. If you ask this question, you can be sure to hear some interesting things the other person’s friends are criticizing about them.

97. How do you kill time?

98. What catastrophe is waiting to happen?

99. What was your “Why didn’t I start this sooner” moment?

100. What’s the nicest thing you’ve ever done for another person?

I hope you enjoyed reading this list of good questions to ask to get to know someone.

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