100 Questions to Ask People Around You

By on January 24, 2015

Whether you want to get to know a date better or just gain insight into a friend, these questions will help you to uncover the answers. Beyond the basic “yes” and “no” questions, these queries are designed to dig deeper into who someone is. You can use these as conversation starters and to break the ice. Asking a question is the first step toward being good at conversing. The next step is to truly listen to the answer. Make sure that you take time to mindfully listen to what your friend has to say—the answers may surprise you.


1.) Question: What teacher made a difference in your life? Who had the largest impact on who you are today?

Why it Works: A teacher plays a pivotal role in forming who we are. They can help us discover a passion and develop our skills. Often, a specific teacher will play a role in what we choose to do later on. The answer to this query will reveal how they got to their current place in life.

2.) Question: If you won the lottery, what would you do with the money?

Why it Works: This is a fun question to get a conversation going. Throughout the conversation, you will find out more about their goals, views on money. Would they leave their career? Travel? Settle down? With unlimited funds, the choices that someone makes are deeply revealing.

3.) Question: What is your favorite childhood memory?

Why it Works: Someone’s childhood is extremely revealing about who they are as a person. The answer could be humorous or reveal a deeply held hope or dream. Knowing about how someone grew up indicates a lot about who they are as a person.

4.) Question: What would you want your tombstone to say?

Why it Works: Obviously, you will need to have a bit of relationship developed before asking this or it will seem extremely odd. This query reveals what someone expects and desires out of life. A person who wants a tombstone to say “Good wife and mother” will have different than someone who wants a tombstone to say, “Noble prize winner.”

5.) Question: If you could re-do one thing in your life, what would you do differently?

Why it Works: At some point, everyone has at least one regret. The answer to this question will indicate what they wanted to do better and their vulnerabilities. Out of the questions to ask people on this list, this is one of the questions that you should wait for later in the relationship to ask. It can be extremely personal, so it is not a question to spring on someone immediately.

6.) Question: What are you the most proud of?

Why it Works: Someone’s greatest accomplishment isn’t always what they are the most proud of. Sometimes, people feel stronger about a decision to start a family or accomplish a goal than they do about an award.

7.) Question: What do you do in your free time?

Why it Works: Everyone has to work, and most of our work hours are controlled by a boss. To really see what someone likes, you have to know how they spend their free time. This part of the day is when they truly get a chance to just be themselves.

8.) Question: What scares you the most?

Why it Works: The answer to this can be extremely enlightening. Our fears are based on childhood experiences, vulnerabilities and our personal passions. If they are afraid of losing a loved one, it indicates a history of strong relationships. Since this is a serious question, you should respond compassionately and listen to their answer.

9.) Question: How did you meet?

Why it Works: If you are talking to a couple, this is a great way to get the conversation started. Happy couples love talking about how they came to be together. In addition to learning about their past, it will allow you to get the conversation flowing.

10.) Question: How do your friends describe you?

Why it Works: This gives the speaker a chance to consider how they are viewed from an outside perspective. It also indicates their personal level of self-awareness.

11.) Question: What is your favorite style of music?

Why it Works: Although this question might not be particularly revealing, it is a great conversation starter. If they have an extremely odd music choice, try asking them about what caused their love of the genre. Often, a close family member or friend is the person who got them interested in a type of music.

12.) Question: Would you rather visit Europe or Mexico?

Why it Works: What you are really asking is if they are the partying, fun-loving type or the classical adventurer.

13.) Question: If you could travel to any country or state, where would you go?

Why it Works: This question is a great way to figure out who they are. You can also use this as a starting point for both of you to share your travel experiences and stories.

14.) Question: What moment has defined your life?

Why it Works: For younger people, this could be an academic competition, sports event or family member. Older individuals may have deeper and more vulnerable defining moments. Often, a divorce, death or cross-country move defines who we become.

15.) Question: What is the scariest thing that you have ever done?

Why it Works: In addition to revealing a potential horror story, this question will also indicate if they are the type of person who likes to take risks.

16.) Question: If you could only keep five of your belongings, what would the be?

Why it Works: Although most people view this as a superficial question, it is actually incredibly revealing. The five possessions that they keep shows what they value and what really matters to their life.

17.) Question: If you wrote a book, what would it be about?

Why it Works: Almost everyone has a novel or non-fiction book idea. What they want to write shows who they are and the type of book that they like to read. Depending on the novel idea, it could spark an extremely interesting conversation.

18.) Question: What is your current profession?

Why it Works: If they are currently work at McDonald’s, don’t give up yet. Although they might not be in their chosen profession, they could be in the process of studying or working toward a new goal.

19.) Question: What made you choose your job?

Why it Works: If they are already in their chosen career field, asking about it could really draw them out of their shell. A chosen profession indicates what someone cares about, their motivations and goals. Since most of us spend 30 to 50 hours a week at a job, this question indicates a great deal about our values.

20.) Question: Who do you admire the most in your life?

Why it Works: Often, people will try to model their lives after a role model. By learning about who they admire, you can understand where your friend wants to go in their life. This question reveals a great deal about their true character.

21.) Question: What is your greatest strength?

Why it Works: This reveals two things: how accurate their self-awareness is and what they value. Someone strives to have strengths that are in line with their personal values. Whether they achieve this or not is up to the individual.

22.) Question: What is your greatest weakness?

Why it Works: Although it may sound like a job interview question, this is another revealing thing to ask. You can also ask them why they view something as a weakness or what they are doing to change it.

23.) Question: What are your top three favorite books? Why?

Why it Works: If you want to find common ground, this is an excellent question to ask. This allows you to learn about the other person. It may also give you the chance to learn something new or gain a different perspective on matters.

24.) Question: Have you been in a car accident? What happened?

Why it Works: Death, taxes and car accidents are the only things that most people have in common. At some point, almost everyone will get into a car accident. Sharing accident tales or driving horror stories can be an excellent way for you two to bond.

25.) Question: What holidays do you celebrate?

Why it Works: Many people celebrate the same holidays. Depending on our ethnic, religious and cultural backgrounds, the way we celebrate could be different. They may have an old holiday tradition that could be interesting to hear about.

26.) Question: Do you consider yourself to be a religious person?

Why it Works: This question should be addressed with great sensitivity. If you are a diehard atheist, telling an avowed Christian that God doesn’t exist will not earn you any friends.

27.) Question: What is your favorite thing about your personality?

Why it Works: Some people will feel uncomfortable answering this question. If they can get their modesty out of the way, this question will indicate what they value about themselves. It can also show their self-confidence levels. If there is nothing that they like in their personality, they probably suffer from low self-esteem.

28.) Question: Do you prefer to read on a Kindle or on paperback?

Why it Works: It may not be the most exciting question, but you would be surprised about how strongly some people feel. Traditionalists believe that a paperback book is the only way while technology-lovers are entranced by the digital options. From this question, you can start further conversations about favorite authors, books and genres.

29.) Question: If you could go back in time or to the future to witness any event, what would it be?

Why it Works: In addition to being an extremely fun question to ask, this question is also a great way to begin an interesting conversation.

30.) Question: What is the best compliment that you ever received?

Why it Works: It might not be the most exciting question, but it can reveal what they value. Someone who values an intelligence-based compliment is inherently different than someone who liked a compliment about how they look.

31.) Question: Have you danced in the rain before?

Why it Works: This question is fun to ask and shows if they are a carefree person. It also could indicate a secret love for classic films like “Singin’ in the Rain”.

32.) Question: If you were the president of the United States, what is the first thing you would choose to do?

Why it Works: During the beginning of a relationship, asking political questions should always be done carefully. This query will show some of their political values without having to ask their voting record. You should always exercise caution, however. If you react with laughter or criticism, they will get offended.

33.) Question: What is the number one thing that you have always wanted?

Why it Works: The answer could be a goal, ambition or belonging. After asking the initial question, you should follow up with, “Did you get it?”. If they are a goal-driven person, they may have already gotten their heart’s deepest desire.

34.) Question: What actions or words feel like love to you?

Why it Works: Everyone has different relationship styles and a personal love language. These words and behaviors constitute how each individual expresses their love. This query is ideal for a potential boyfriend, spouse or romantic partner.

35.) Question: Do you like traveling?

Why it Works: Someone who likes to travel generally likes sharing their stories. By starting a conversation off with this, you can also tell if they are a homebody or a travel nut.

36.) Question: Would you rather vacation in Alaska or Hawaii?

Why it Works: This can reveal several things. While Hawaii is a traditional, popular, sunny location, Alaska is a common choice for the cold-loving adventurer. It is up to you to ask more questions and determine what qualities your friend has.

37.) Question: What age do you feel right now? Why?

Why it Works: Among the older generation, the answer to this question can be revealing. Most people over the age of 50 do not feel like they are actually that old. The answer is enlightening because it shows how someone feels on the inside, even if they look differently on the outside.

38.) Question: Who is your favorite author?

Why it Works: This is a chance for you to bond over shared authors and experiences. It is also an opportunity for you to learn about a new author or genre.

39.) Question: What is one skill that you are interested in learning?

Why it Works: Many people take time for self-improvement. Other individuals like to learn new skills because they enjoy it. The answer to this shows what someone desires to do. Follow it up by asking if they ever learned the skill. The life events or barriers stopping someone from achieving a goal can be just as revealing as the goal itself.

40.) Question: Would you rather stay in a hostel, hotel or with a friend?

Why it Works: As far as questions go, this is not the most exciting one of these questions to ask people. Use this as a way to get the conversation going again. Also, ask your friend why they chose a particular option. Do they like alone time? Or would they prefer to meet people in a hostel?

41.) Question: What do you consider your most embarrassing moment to be?

Why it Works: We can try to connect over our shared interests, but laughter is generally a better way to relate. If they share their deepest, darkest secret with you, make sure that you do likewise. A funny story gives you a chance to laugh something off. If the embarrassing tale is particularly painful, you should express empathy for what they went through.

42.) Question: Have you ever considered adopting?

Why it Works: People adopt for many reasons. Other than an inability to have children, one of the most common reasons is because they actually care. Someone who wants to adopt a second or a third child will generally be an extremely compassionate, empathetic person.

43.) Question: What does your perfect day look like?

Why it Works: This could be a perfect day that they have had or something that they hope for. Besides starting the conversation, this question will also help to boost your friend’s mood. Daydreaming about a perfect day or remembering a good event is always a happy experience.

44.) Question: Would you rather go to a film, play or musical?

Why it Works: Asking this shows how cultured the individual is. Perhaps they participated in theater in high school or watched Moulin Rouge too many times. Whatever the answer, it will show something new about your acquaintance.

45.) Question: What was the last picture you took on your phone?

Why it Works: The answer to this is a basic way to get the conversation going. They may have taken a picture from a recent hike or of their daughter’s first steps. Whatever the candid moment was, it most likely was the last semi-major event of their life. As such, it is a great way to begin a conversation.

46.) Question: Do you know about your heritage?

Why it Works: Family histories and traditions are always interesting. Growing up, one of my teachers used to gather with her family each year to make sausage. From standard to unusual, these stories can be extremely enlightening.

47.) Question: Do you enjoy gossiping?

Why it Works: Among women, the most common answer is yes. Most ladies won’t admit to it, but there is something enjoyable about sharing secrets about co-workers and friends.

48.) Question: What was the last time that you lied?

Why it Works: There are actually people in the world who have never lied. Your friend could be one of these individuals, or she/he could have an engaging story to tell about their last lie. Among adults, the most common thing to lie about is an illness. Calling in “sick” to work is so common that it is a popular theme in comic strips.

49.) Question: What are some of your favorite movies?

Why it Works: This question may not be thrilling, but it offers a chance for you to bond over shared interests.

50.) Question: What is your blood type?

Why it Works: In the United States, there are many people who don’t actually know their blood type. Among the Japanese, someone’s blood type is thought to indicate their personality type.

51.) Question: Have you ever run a marathon? What are some of your fitness goals?

Why it Works: A surprising number of people have a marathon listed on their bucket list. If you share the same exercise goals, you may even have a new workout buddy.

52.) Question: What is your favorite type of beer?

Why it Works: Are they a hipster who likes microbreweries or a frat boy who goes for Natural Ice? This question can be revealing on so many levels. If you are not sure how to characterize a drink preference, you can always ask your local bar tender for a stereotype.

53.) Question: What caused you to get into your current career field?

Why it Works: Some people just fall into a career. For most workers, a career was deliberately chosen based off of a role model, past experience or unique opportunity.

54.) Question: Have you ever been pulled over by a cop?

Why it Works: Like the car accident question, most people have probably been pulled over at some point. Share your stories of the most recent time that you were pulled over.

55.) Question: What do you do for fun?

Why it Works: Even if you have already asked about their hobbies, this question could still get a different answer. Someone might enjoy their hobby, but their idea of a fun activity could be entirely different.

56.) Question: Are you married?

Why it Works: If this is a date, you should already know if they are married. With a new friend, this is a good question to ask. You can inquire about their spouse or share stories from your own relationship. They may also want to share the story of how they met their spouse.

57.) Question: What is one thing that you have learned in life?

Why it Works: The answer to this can show if they view the glass as half empty or full.

58.) Question: Do you have any kids?

Why it Works: This is a must-have question for any date. Whether you love or hate children, you should be forewarned about any kids that your date has. You need to know if you will be a surrogate mother before things start to get serious.

59.) Question: Would you recommend your career to someone else?

Why it Works: Someone may choose a career that they are passionate about and get burned out later on. You can ask this to find out if they are happy about their career choice and how they currently feel about their line of work.

60.) Question: What did you want to be when you were a child?

Why it Works: After the previous question, this can be a great followup query. As we learn more about life and narrow our focus, a career dream from childhood may disappear. This questions will illuminate who they were and how it compares to who they have become.

61.) Question: What culture is the most interesting to you?

Why it Works: Other than revealing a potential travel goal, this question will show their current interests. You should also ask how they developed that interest. They may have taken a class in school or had a friend from that culture.

62.) Question: Who would you like to meet?

Why it Works: Not everyone can meet their favorite celebrity, but it is always interesting to find out who someone wants to interact with.

63.) Question: What is your weirdest habit?

Why it Works: Perhaps your friend is OCD and taps the door handle three times. They may have particular towel-folding requirements, an unusual pre-bed tradition or an odd quirk. This question helps to humanize them and allows you to relate to your friend on a more personal level.

64.) Question: Would you rather be ugly and live for an eternity or die beautifully within the year?

Why it Works: Fun to ask, this question shows their narcissistic tendencies. A modification of this question would be to ask: “Would you rather live to 90 with perfect mental abilities and an old body, or declining mental function and the body of a 50-year-old?”

65.) Question: What are some of the things that make you happy?

Why it Works: You should know how to make any friend, date or partner happy. When someone is having a bad day, you can make it better if you know the answer to this question. A favorite cupcake, a surprise rock climbing trip or another token of love is all it takes to turn someones day around.

66.) Question: Have you ever prank called someone? What did you say?

Why it Works: Almost everyone prank called as a teenager or child. Some of the better pranks are well-worth telling.

67.) Question: Who do you trust in your life? Do you trust anyone?

Why it Works: Even the nicest of people could have trust issues. An inability to trust does not mean that you cannot be with a guy. It just means that you will have to work a little harder at earning their trust.

68.) Question: Is there anyone that you would die for?

Why it Works: This is a very serious question. They may never have to actually live up to your answer, but you should not take their response lightly. Who your friend would die for indicates the people that they care about.

69.) Question: Do you get along with your family?

Why it Works: Everyone says that they have a crazy family, but some people actually do. Once you get to know someone fairly well, you can ask this question to find out how strong their familial relationships are.

70.) Question: Is there a situation where you would torture someone? Who would it be and why?

Why it Works: Scientific studies have showed that the average person can and will torture if put into a specific situation. Even without being in a bad situation, there are cases where a normal, caring person could do unspeakable things. Common answers include torturing for a family member or to protect a large number of people. Be careful with this question because it can devolve into a heated debate.

71.) Question: You discover that your toddler was mixed up at birth do to a hospital mistake. Would you want your biological child or the one that you have grown to love?

Why it Works: If you have problems making conversations, talking about unique, weird situations like this could help catalyze an interesting conversation.

72.) Question: Would you be willing to eat a bowl of crickets for $5,000? One million dollars?

Why it Works: Again, this is another question that is just intended for fun.

73.) Question: Would you lie in court to save a friend from life in prison?

Why it Works: This question reveals how strongly they value following the rules and being honest. It also indicates the quality of their personal relationships. Would you lie in court and risk perjury charges to save a friend?

74.) Question: What is the first thing that you think of when you wake up? What is your morning ritual?

Why it Works: Is your friend a morning person? Do they write a novel before they go to work? Or are they the type of person who rolls out of bed before they dash out of the door?

75.) Question: If you could have any super power, what would it be?

Why it Works: According to dream analysts, our dreams at night indicate how we feel. People who want to fly are searching for freedom or an escape. Individuals who want super strength feel like they lack empowerment in their normal life. More importantly, you should ask what they would do if they possessed their dream super power.

76.) Question: If you could do anything right now, what would it be?

Why it Works: If you are on a date, the answer will hopefully be that he wants to be right there with you. Other than this corny, romantic response, other answers could illuminate someone’s goals or their favorite pastime.

77.) Question: Do you think that children should be sheltered from sadness?

Why it Works: Answering this question is rather tough. Although children should be protected from tragedy and abuse, it is not always possible. Additionally, they will have to learn how to feel with negative emotions someday. Deciding when that day arrives can be hard for even the best of parents.

78.) Question: What is the question that you really hate to answer?

Why it Works: Good news: By asking this question, you prevent yourself from asking the one they actually hate to answer. As a side benefit, they will most likely answer the hated question anyhow.

79.) Question: If you could wake up in someone else’s body, who’s body would you choose?

Why it Works: We are constantly bombarded with media images that tell us what we should look like and what we should do to be attractive. If we are going to spend a lot of our lives worrying about looks, we may as well have fun with it by using questions like this.

80.) Question: If you were on a deserted island, who would you want to bring with you?

Why it Works: This can be a hard question to answer. You’d want someone enjoyable and interesting, but relaxing enough to be around 24/7.

81.) Question: What has been your biggest challenge?

Why it Works: Again, this is an excellent way to discover their goals.

82.) Question: If you had to eat the same meal for the rest of your life, what would it be?

Why it Works: When you are stuck for something to say, questions like this are fun.

83.) Question: If you had all the money in the world, how would you spend your time?

Why it Works: If they are already spending their time how they would want to, you have met an extremely well-balanced person.

84.) Question: Do you think college or life experience prepares you better for work?

Why it Works: Academics may argue, but there are some points to be made in favor of life experience.

85.) Question: What is your favorite memory?

Why it Works: Sharing favorite memories is an excellent way to find out more about them.

86.) Question: What was your favorite thing to do in gym class?

Why it Works: If you are on a date, this question could be a great idea for a future date. Rock climbing, anyone?

87.) Question: If you were an artist, what would be your medium?

Why it Works: Are they more of an oil painting type or a sculpture? Or, of course, there is the artist who made the Virgin Mary out of elephant dung…

88.) Question: What is one thing that you think should be taught in school and isn’t?

Why it Works: This answer could be developed from their life experience or the classes they took in college. The modern education system needs an overhaul, so there are plenty of answers available.

89.) Question: Do you play an instrument?

Why it Works: Many people played an instrument as a child or were in a band. Sharing stories and playing together could be fun for both of you.

90.) Question: What does your current life say about who you are?

Why it Works: Our decisions, unavoidable events and loved ones play a strong role in who we are. Out of those factors, it is our decisions that are the most interesting.

91.) Question: What is t he longest that you have gone without sleep? Why?

Why it Works: The majority of people love sleep and would never choose to stop sleeping. Learning why they stayed up so late is just as important as the fact that they did.

92.) Question: If someone gave you a brainwashing machine, who would you use it on? Why?

Why it Works: Over the years, they may have had an embarrassing moment, a bad breakup or a tragedy that they want to erase from their mind. For embarrassing moments, they may want to erase it from the mind of someone else as well.

93.) Question: What is the strangest thing that you ever eat?

Why it Works: This question could be divided into the strangest foods from childhood and as an adult. Children often eat bugs or similar items, but adults choose what they eat. A shot of snake venom or a bite of squid probably carry an unusual story.

94.) Question: What cheers you up when you are sad?

Why it Works: In addition to learning what they like, this answer will show how you can cheer them up on a bad day.

95.) Question: What is the one thing that you are always losing.

Why it Works: This list will probably be topped by keys and cellphones.

96.) Question: Tell me about something that happened to you that you have no explanation for.

Why it Works: You might not believe in ghosts, but there are always spooky things that occur without a discernible reason. Gather around the campfire and prepare to be intrigued.

97) Question: What is your favorite word?

Why it Works: Bibliophiles and grammarians love questions like this.

98.) Question: Is there anyone who goes to you for advice?

Why it Works: If you are running out of things to ask, this could be a decent question.

99.) Question: What did you do on your last birthday?

Why it Works: A birthday is one of the few days that nearly everyone can get off of work and spend how they want. What someone chooses to do on their birthday demonstrates what they care about. Who they spend their birthday with shows who they care about.

100.) Question: Is there anything that I should know?

Why it Works: This is a good time for a date to share any children, dangerous diseases and criminal history. It also means that you can remind them in the future that you did ask about their past. For a new acquaintance, this question is a chance for them to tell you something that you never thought to ask.

These questions to ask people around you are designed to get the conversation going. Ranging from funny to serious topics, these questions will help you to find out more about the people around you. If you have a favorite or an idea for a question that we forgot to list, post it in the comment section below!

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