Best Questions to Ask Someone

One way to learn about a person is to watch them, but that has its limitations. We can see what’s important to them by what they spend their time or money on. We can follow their social media to see what their interests or political leanings are. However, if we really want to learn more deeply about people around us, the best way is to combine what we see them doing with their own verbalized thoughts. This is why asking people questions is important. 

Everyone wants to feel that their opinion and feelings matter and that someone is interested in who they are and what they have to say. Plus, who doesn’t like talking about themselves? Starting with more shallow questions can still lead to deeper discoveries about a person. Knowing how to ask someone great questions helps them to know that you care about what they think. And, in turn, they will tend to like you more because you showed them that you care enough to ask them about themselves. 

Best Questions to Ask Someone

You will probably find that some of the questions in here that seem shallow, may, in fact, lead to some profound discoveries about each other. The goal here is to help you to strike up a conversation and to help you to connect with other people. We are on this planet with billions of other people. We should have some knowledge of how to speak to them. The categories have links on them to help you navigate and be able to simply jump to whichever one suits your fancy. Enjoy the connections you are about to make!

FunIce BreakerGood General Questions


Fun Questions to Ask

1. Do you think you could live without the internet?

2. What’s the best thing that has happened to you in the past week?

3. What is one of your most memorable birthdays?

4. What’s the best concert you’ve ever attended?

5. If you were stranded on a desert island with only one item, what would it be?

6. What would you consider to be your spirit animal?

7. If you could travel back in time and meet one person from history, who would it be?

8. What’s your guilty pleasure?

9. If you could survive on one single type of food for the rest of your life, what would it be?

10. What do you think you could give an hour-long presentation on with zero preparation beforehand?

11. What would be the first thing you’d do if you won the lottery?

12. Would you rather go skydiving or whitewater rafting?

13. When was the last time you tried something to look cool, but it ended in complete humiliation?

14. Is there a fictional place you would absolutely love to visit? 

15. What is your favorite meme or Vine compilation?

16. What is the most useless thing you’ve ever bought?

17. What is your stupidest fear?

18. What are some of the best lousy pickup lines you’ve ever heard?

19. What’s the best pizza topping combination?

20. What’s your idea of the perfect adventure? 

21. If you could wave a magic wand and change anything about your life, what would it be?

22. What’s a better way to vacation: planning every day and activity out so you get to do/see everything you want, or simply going with the flow?

23. If you were to host a dinner party and invite one musician, a politician, a famous couple, and one single family member, who would you invite?

24. Have you ever gotten into a physical altercation with someone over something completely ridiculous?

25. What is some slang that the kids use these days that makes you feel old?

26. If you could be given any nickname, what would it be?

27. What’s your guilty pleasure?

28. What would your dream house look like?

29. Should the toilet paper roll be pulled under or over?

30. Would you rather be half your height or double your weight?

31. Would you rather go camping in the woods or chillax at a beach resort?

32. Would you rather feel itchy or sticky for the rest of your life?

33. Would you rather live with the hiccups or the constant need to sneeze and never be able to forever?

34. If you were in a band, what kind of music would you play?

35. Where would you hide if you were suddenly a fugitive?

36. Which would you rather do, skydive or swim with sharks?

37. What’s your least favorite word?

38. What’s your favorite candy?

39. What are your thoughts on clowns?

40. What’s the best gift you’ve ever given?

41. What’s an obscure food that you’ve eaten that most people probably haven’t?

42. If you were guaranteed the correct answer to one single question, what would that question be?

43. What’s one word that sums up your entire personality?

44. What is the most interesting scar you have? How did you get it?

45. What’s the worst pizza topping?

46. What’s the worst ice cream topping?

47. If one animal grew to be the size of a whale, which animal would be the most terrifying?

48. What’s one terrible thing you remember your mom catching you doing as a kid?

49. Who do you think is one of the most annoying celebrities?

50. What is the weirdest topic you have researched on Wikipedia, and it continued to lead you to other topics? 

51. What is the best vacation or trip you have been on?

52. What’s one activity that you regularly did as a child that no kids do nowadays?

53. What is one physical attribute you like about yourself?

54. If you could write your own obituary, what would you write?

55. Thank goodness it’s Friday! Do you usually stay in or go out?

56. If you could pick any animal to talk, which would it be?

57. What smells make you happy and bring back good memories?

58. What’s the most bizarre chewing gum flavor you can come up with?

59. Do you think you have ever seen a ghost?

60. What is your favorite thing about your best friend?

61. What would you do if you had 24 hours to spend in this city/town?

62. If you went to Hogwarts, which house would you like to belong to?

63. If you were given one million dollars, what is the first thing you would spend it on?

64. What is one of your favorite viral videos?

65. Which celebrity do you really not like?

66. Did your parents name you after someone?

67. Did you have a favorite bedtime story?

68. Did you like going to school as a kid?

69. What was your wedding like?

70. Would you rather be as small as a gnat or as huge as a dinosaur?

71. If you were a snake, how long would you want to be?

72. If you had to choose one of these two foods to be eliminated from the earth, which would it be? Burgers or tacos?

73. Would you rather be too warm all the time or too cold all the time?

74. Do you prefer Pepsi or Coke?

75. Which makes you the least uncomfortable: mustaches or beards?

76. Do you prefer riding planes or trains?

77. What’s the longest amount of time you’ll leave a dropped piece of food on the ground and still be okay with eating it?

78. In a story about your life, do you think you’d be considered the hero or the villain?

79. If Jurassic Park was real, would you visit it?

80. Would you accept an invitation to travel to outer space?

81. What do you think is the best feeling in the world?

82. If you had to choose between losing a leg or growing a tail, which would you choose?

83. Have you ever farted in an enclosed space and pretended it wasn’t you or even blamed someone else?

84. If your pet could speak, what would s/he write about you when asked if you’d make a good fit for a promotion?

85. What’s the most amazing slow-motion video you’ve ever seen?

86. What’s the most expensive thing you’ve ever broken?

87. What’s the spiciest thing you’ve ever eaten?

88. What obstacles do you think would go in the world’s hardest obstacle course?

89. Do you know any riddles?

90. What’s your cure for hiccups?

91. What’s an invention that doesn’t get a lot of recognition but has dramatically improved the world?

92. If you could choose someone to narrate your life, who would you choose?

93. If you could be awarded a Ph.D. degree in something that you already know a lot about without attending any of the required courses, what would your Ph.D. be in?

94. What smartphone feature would you be excited for phone companies to implement?

95. What’s the funniest name you’ve heard of someone having?

96. What movie/TV show character would you love to swap lives with for a week?

97. If magic was real, what’s the spell you would try to learn first?

98. Which protagonist from a book or movie would make the worst roommate?

99. What’s the most passive-aggressive comment you can think of?

100. What’s the most boring superhero you can come up with?


Ice Breaker Questions

1. Do you have a favorite artist?

2. In your opinion, what is the most effective way to procrastinate?

3. Are you an early bird or a night owl?

4. What’s something you wish you were better at?

5. What’s your favorite breakfast food?

6. What’s your favorite movie/book genre?

7. What’s a TV or YouTube channel that doesn’t exist but you think should?

8. What city would you most like to live in?

9. What trend or fad would you be least mad about if it made a comeback?

10. What’s something you’re most likely to become famous for?

11. Where is the most relaxing place you’ve ever been to?

12. What’s one popular TV show or movie that you absolutely refuse to watch?

13. What does your ideal weekend look like?

14. In your opinion, what are some small things that could totally turn a crappy day into a great one?

15. What’s the best thing that happened to you last week? What’s the worst thing?

16. What’s the most impressive thing you know how to do?

17. What’s the best book or series you’ve ever read?

18. What’s something you’re interested in that most people probably haven’t heard of?

19. If you suddenly became a master at woodworking, what would be the first thing you’d carve?

20. If you didn’t have to sleep to survive, what would you do with all that extra time?

21. What’s something special about the place where you were raised?

22. How did you and your best friend meet?

23. How long have you been friends with your best friend?

24. Do you have any upcoming travel plans?

25. When you’re not working, how do you like to spend your time?

26. What’s your favorite 90s TV show?

27. What’s your dream job?

28. What’s your most-used emoji?

29. If you could change your name, what would it be?

30. Do you have any hidden talents?

31. If you could spend a day in someone else’s shoes, whose would they be?

32. If you could instantly become an expert at something, what would it be?

33. What would your dream day look like?

34. What’s a weird food combination that you enjoy?

35. What’s a food that you’ve never eaten but would like to try?

36. In your opinion, what’s something that will always be in fashion?

37. Is there something that makes you roll your eyes every time you hear it?

38. What’s something that you think you’re better at than you are?

39. What’s the most creative use of emojis you’ve ever seen?

40. What’s the funniest joke you know by heart?

41. What movie quotes do you use regularly?

42. When someone asks you for music recommendations, what band or artist do you always recommend to them first?

43. What’s the funniest thing you’ve accidentally done while distracted or daydreaming?

44. What’s the most interesting documentary you’ve ever watched?

45. What’s an app you can’t believe hasn’t been made yet?

46. What’s the most extreme amount of procrastination you have ever done?

47. What word is a lot of fun to say?

48. What’s your go-to restaurant?

49. What languages do you wish you could speak?

50. What’s one habit that you have now that you wish you could have started earlier?

51. If you could know the truth behind any conspiracy, but would instantly die if you let it slip to anyone that you DID know the truth, what theory would you want to know about?

52. What’s the opposite of a koala?

53. What do you like to cook?

54. What movie universe do you think would be the worst to live in?

55. What life skills do you think are rarely taught but extremely useful?

56. What’s the most ridiculous animal on the planet?

57. What’s the most historic thing that has happened in your lifetime?

58. What’s the most recent show you binge-watched?

59. What’s the worst movie trope?

60. What did you Google last?

61. What would be the most interesting way to travel if money and practicality weren’t an issue?

62. What’s the most frustrating city you’ve ever lived in?

63. What’s cheap, but you would willingly pay more for?

64. What would the adult version of an ice-cream truck sell, and what song would it play?

65. What do you think is the most overrated brand?

66. What would be an accurate tag line for each month of the year?

67. What time of day are naps most satisfying?

68. What was the worst shopping experience you ever had?

69. If you were a clown-themed superhero, what powers would you have?

70. What would a VR world of your own design look like?

71. What did you believe in for way too long as a child?

72. What two things are awful when separate but great when you put them together?

73. What’s something that still makes you cringe when you think back on it?

74. What colossal event do you think will happen soon that you don’t think anyone will be ready for?

75. If you owned a restaurant, what kind of food would it serve?

76. What kind of food would be served at a massive feast in your honor?

77. What’s the weirdest crush you’ve ever had?

78. What’s your favorite Hallmark movie?

79. What pop-culture elements are forever tied to your childhood?

80. Who is the most creative person you know?

81. What’s your good luck charm?

82. What is the oldest thing you own?

83. What’s something someone has borrowed from you but never given back?

84. If cartoon physics replaced real physics, what’s the first thing you’d want to try?

85. What’s the most advanced form of technology that you’re eager to get your hands on?

86. What’s something from the present that you think will withstand the tests of time?

87. What’s the most disgusting sounding word in the English language?

88. What’s your first reaction when you hear something fall in the middle of the night when you’re in bed?

89. What outfit could you put together with clothes that you own that would get the most people to laugh?

90. What was ruined because it became popular?

91 Do you use any slang on a regular basis?

92. What topic could you spend hours talking about?

93. What is something that a lot of people hope will happen, but it never will?

94. What’s the most rage-inducing game you’ve ever played?

95. If you had a perfect day, what would that consist of?

96. What’s an awful movie that you enjoy watching?

97. What’s a typically delicious food that gets ruined when you wrap it in a tortilla?

98. What’s something you were entirely sure of until you found out you were categorically wrong?

99. What’s something normal that people do, but that seems weirder and weirder the longer you think about it?

100. What’s the cutest thing you can imagine?


Good General Questions

1. What’s the most heartwarming thing you’ve ever seen?

2. What pets did you have growing up?

3. What’s the luckiest thing that has ever happened to you?

4. Do you think you are an introvert or an extrovert?

5. Why did you decide to do the work you’re doing now?

6. Who do you look up to? Why?

7. If you had two hours left on this earth, what would you do?

8. What is your favorite Disney movie?

9. What is something you have done that you are proud of?

10. What book has influenced your life?

11. What movie has influenced your life?

12. What is a good piece of advice you have received lately?

13. Are you a risk-taker?

14. What is a significant risk you have taken recently?

15. What is your favorite thing about where you are working right now?

16. What is a hobby you would like to develop?

17. If you opened a restaurant, what would you name it?

18. What is one thing people do that makes you feel loved?

19. What makes you happy?

20. If you could change something about your job, what would it be?

21. What’s something you say you’ll do but probably never will?

22. Do you think there are things about you that people often misunderstand? If so, what are they?

23. What are you most grateful for?

24. In your opinion, what is one societal stigma that needs to be changed?

25. What would a world populated by clones of you be like?

26. Do you think aliens exist?

27. What movie can you watch over and over again without getting tired of?

28. When you’re old, what do you think young people will ask you to tell stories about?

29. How do you think the country would change if everyone could vote, regardless of age?

30. What animal would be cutest if scaled down to the size of a cat?

31. What’s the most epic way you’ve seen someone fired?

32. Who is an actor that plays the same character in every role they land?

33. If you were a pharaoh in ancient Egypt, what kinds of items do you think you’d be buried with to take into the afterlife?

34. What are some “old person” habits that you’ve come to acquire?

35. When was the last time that you got to tell someone, “I told you so,” and what is the story behind it?

36. Do you think kids born today will have better or worse lives than their parents?

37. What’s something you think people should worry about, but they don’t?

38. What was cool when you were young, but isn’t cool anymore?

39. What goal do you think humanity isn’t focused enough on achieving?

40. What’s a game that you’ve wasted countless hours playing?

41. If you could have an all-expenses-paid trip to see any world monument, what would you want to see?

42. How far past the expiration date is too far, assuming the food both smells and looks completely fine?

43. Who is the funniest comedian you know of?

44. What song hits you hard every time you hear it?

45. What’s something that would make you facepalm?

46. What’s something that needs to be modernized?

47. If you had zero filters between your mouth and your brain, who do you think would stick with you through your life?

48. What’s the best thing you could reasonably expect to find in a cave?

49. What’s one bit of trivia you know that is very useless?

50. What’s something you did that you expected to be amazing, but it was actually awful?

51. What’s one thing that you thought would be awesome about being an adult when you were a kid, but isn’t all that awesome now that you’re an adult?

52. What’s something that you think everyone in the world–absolutely everyone–can agree on?

53. In your opinion, what’s the most pleasant-sounding foreign accent?

54. What’s some insider knowledge that people in only your line of work know?

55. Who do you wish you could get back in contact with?

56. What do you think is the strangest country?

57. What’s the closest brush with death you’ve ever experienced?

58. If people receive purple hearts for bravery, what would other colors represent?

59. What’s the worst hairstyle you ever had?

60. What animal would be the most terrifying if it could speak?

61. What’s your funniest story involving a trampoline?

62. When was the last time you acted nonchalant but were dying on the inside?

63. If you built a themed hotel, what would the theme be?

64. What scientific discovery would change the course of humanity overnight if it were discovered?

65. Do you think that humanity will ever reach a state of peace?

66. What brand are you most loyal to?

67. If you could disappear and start a whole new life, what would you want that life to look like?

68. What’s the most awkward thing that happens to you regularly?

69. What is the least scary horror movie you’ve ever seen?

70. What movie, book, or TV show do you know the most quotes from?

71. What’s a relatively common experience that people have that you’ve never had?

72. What’s a quality that all your friends have in common?

73. What’s a weird smell that you like?

74. What’s the saddest scene in a movie or TV show that you’ve ever seen?

75. What’s the coolest animal in the world?

76. What fashion trend makes you cringe or laugh every time you see it?

77. Which apocalyptic dystopia do you think is most likely to happen?

78. What’s the most beautiful beach you’ve ever been to?

79. What’s something that everyone agrees should be changed, but somehow it never changes?

80. What’s the most embarrassing story from your childhood?

81. What’s the weirdest text you’ve ever gotten?

82. What’s something that always cheers you up?

83. What sport could you play the longest in a televised game, without anyone discovering you aren’t a professional athlete?

84. What fictional characters have you had a crush on since you were a kid?

85. Do you think things should be thoughtfully planned, or should everyone just go with the flow?

86. What was the worst shopping experience you ever had?

87. Who is the most manipulative person you’ve ever met?

88. How ambitious are you?

89. What did you love/hate about where you grew up?

90. When was the last time you stayed up all night?

91. What’s something that people think makes them look cool, but actually, just makes them look stupid?

92. What’s the coolest hike you’ve ever been on?

93. Would you want the ability to hear other people’s thoughts if you had no control over whose thoughts you heard, and the ability was constant?

94. What’s the darkest movie you’ve ever watched?

95. What’s the biggest realization you had about yourself?

96. What’s something that happens regularly today that would horrify people 100 years ago?

97. In your opinion, what’s a small change people can make that dramatically improves their appearance?

98. What’s the most physically painful thing you’ve ever experienced?

99. When you are at work, what is the most stressful thing for you?

100. If you could choose an age to stay forever, what age would you choose?