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Light · 84 questions

Easy openers. Safe for anyone.

1. Have you been to one of these before?
2. What brought you here today?
3. What's kept you busy this week?
4. Have you found anywhere good to eat around here?
5. Are you local, or did you travel in?
6. What's the last good thing you watched?
7. How's your week been treating you?
8. Have you got anything planned for the weekend?
9. What's something you're looking forward to?
10. Is this your usual sort of thing, or a one-off?
11. What did you do before this?
12. Have you been anywhere interesting recently?
13. What's the best thing about where you live?
14. Are you following anything at the moment — a show, a league, a series?
15. What's your commute like?
16. Do you know many people here?
17. What's the last thing you learned that stuck with you?
18. Have you picked up any hobbies lately?
19. What's your take on this venue?
20. What would you be doing if you weren't here?
21. How did you hear about this event?
22. Which coffee place around here is worth the line?
23. Are you more of a dog person or a cat person?
24. By any chance, have you tried any new restaurants lately?
25. Which season do you look forward to most?
26. Do you have a go-to order at your favorite takeout spot?
27. Describe the best concert you've been to.
28. How do you usually spend a rainy Sunday?
29. Which app on your phone do you use way too much?
30. Is there a book you've been meaning to finish?
31. Do you cook much, or are you a takeout pro?
32. Which sports team do you root for, if any?
33. How long have you lived in this area?
34. Any trips coming up that you're excited about?
35. Which show are you watching right now that I should try?
36. Is there a local spot you think is underrated?
37. Deep down, do you have any pets? Tell me about them.
38. Which podcast have you been hooked on lately?
39. How do you take your coffee?
40. Tell me the best thing you've eaten this month.
41. Are you a morning person or a night owl?
42. Which holiday is your favorite to celebrate?
43. So, have you seen any good movies in theaters recently?
44. Beach or mountains?
45. Which hobby would you take up if you had more time?
46. How was the traffic getting here?
47. Is there a festival or fair around here worth going to?
48. Would you say you play any games, board games or video games?
49. Which city have you visited that you'd go back to?
50. Tell me how you know the host.
51. Are you working on anything fun outside of work?
52. Which snack at this table is the best so far?
53. How do you usually spend your lunch break?
54. Do you have any weekend rituals?
55. Which kind of music gets you going in the morning?
56. Lately, have you picked up any good habits this year?
57. Tell me about a recent small win.
58. Is there a café around here with good pastries?
59. Do you like hiking or biking around here?
60. Which part of town do you like best?
61. How did your weekend go?
62. Are you into any sports yourself?
63. Which restaurant would you take a visitor to?
64. Do you usually go to events like this solo?
65. Tell me the funniest thing you saw this week.
66. By any chance, have you been to the farmers market here?
67. Which gadget could you not live without?
68. How do you like to unwind after work?
69. Is there a new place in town you're curious about?
70. Do you have a favorite local park?
71. Which store could you spend hours in?
72. Tell me about the last road trip you took.
73. Are you planning anything for the holidays?
74. Which topping belongs on pizza, in your opinion?
75. How do you pick what to read next?
76. Have you ever lived anywhere else?
77. Do you follow any fun accounts online?
78. Which part of the year is busiest for you?
79. Tell me about a class or workshop you've enjoyed.
80. Is this weather normal for this time of year?
81. Which dessert can you never say no to?
82. How do you usually get around town?
83. Do you collect anything?
84. Which local event do you never miss?

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Deeper · 83 questions

Personal, but not heavy.

1. What's the most interesting part of what you do?
2. How did you end up in this line of work?
3. What's changed most about your field in the last few years?
4. What's something you've changed your mind about recently?
5. What would you be doing in a completely different life?
6. What's a project you've genuinely enjoyed?
7. What do people usually misunderstand about your job?
8. What's the best advice you've been given?
9. What are you trying to get better at?
10. What's something you'd recommend that almost nobody knows about?
11. What's a decision you're glad you made?
12. What do you read or listen to that shapes how you think?
13. What's the hardest part of what you do?
14. What made you move here?
15. What's something you've been curious about lately?
16. Who's someone in your field you really admire?
17. What's a trend you think is overrated?
18. What did you want to do when you were younger?
19. What's the most useful thing you've learned this year?
20. What would make this year a good one for you?
21. How did you get into the work you do now?
22. Which part of your job makes time fly?
23. Walk me through a mentor who made a difference for you.
24. Is there a skill you're learning right now?
25. How do you balance work with everything else?
26. Which book changed the way you see things?
27. Deep down, do you think you'll stay in this city long term?
28. How would your friends describe you?
29. Which job would you try if you could switch for a year?
30. Share the story of the best team you've ever been on.
31. Are there any causes you care a lot about?
32. How did you choose where you live now?
33. Which small change made a big difference in your life?
34. Honestly, do you have a goal you're working toward this year?
35. When it comes down to it, how do you decide what's worth your time?
36. Which place you've traveled taught you the most?
37. I'd love to hear about a risk you took that paid off.
38. Is there a talent you have that most people don't know about?
39. How has your work changed since you started?
40. Which person has influenced your career most?
41. Do you think you'd be good at running your own business?
42. When it comes down to it, how do you usually handle a really busy week?
43. Which part of your background shaped you the most?
44. Tell me about something you built or made that you're proud of.
45. Are you more of a planner or a go-with-the-flow type?
46. What keeps you curious?
47. Which advice would you give someone starting out in your field?
48. Do you volunteer or help out anywhere?
49. How do you like to learn new things?
50. Which habit helps you most on a hard day?
51. Tell me about the first job you ever had.
52. Is there a question you get asked all the time about your work?
53. How has where you grew up shaped you?
54. Which moment made you choose your path?
55. Do you prefer working with people or on your own?
56. How do you pick your friends as an adult?
57. Which part of your week do you look forward to most?
58. Tell me about a time you were totally out of your comfort zone.
59. Are you happy with how you spend your free time?
60. How have your interests changed over the years?
61. Which tradition from your family do you still keep?
62. Do you think people are born creative or learn it?
63. How do you know when a project is going well?
64. Which challenge are you facing at work right now?
65. Tell me about a time a stranger was kind to you.
66. Is there a place that feels like a second home to you?
67. How do you make big decisions?
68. Which idea have you been thinking about a lot lately?
69. Do you set yearly goals, or just see where things go?
70. How has technology changed your daily life?
71. Which part of growing up here or elsewhere do you miss?
72. Tell me what you're reading right now and why.
73. Are there any fields you wish you knew more about?
74. How did you meet your closest friend?
75. Which kind of people do you click with right away?
76. Do you like the pace of life around here?
77. How do you spend time with your family these days?
78. Which accomplishment are you quietly proud of?
79. Tell me about something you taught yourself.
80. Is there a trip you're saving up for?
81. How do you stay motivated when work gets dull?
82. Which question do you like being asked at events like this?
83. Where do you go when you need to think?

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Deepest · 83 questions

The ones that stay with you.

1. What are you working toward that has nothing to do with your job?
2. What would you do if money genuinely wasn't a factor?
3. What's the biggest turning point you've had?
4. What do you think you'd regret at seventy?
5. What's a belief you hold that most people around you don't?
6. What's the hardest thing you've had to learn about yourself?
7. When did you last feel completely out of place?
8. What's something you've stopped chasing, and are you glad?
9. What do you want to be different a year from now?
10. What's a conversation that changed how you saw something?
11. What are you more afraid of than you let on?
12. What have you outgrown recently?
13. What do you think you're doing mostly out of habit?
14. What's a question you wish people asked you?
15. What does a life well spent look like to you?
16. What did you have to unlearn from how you were raised?
17. When were you last genuinely surprised by yourself?
18. What are you protecting that maybe you shouldn't be?
19. What's something you'd do differently if you started again?
20. What matters to you now that didn't five years ago?
21. Which moment in your life made you who you are today?
22. These days, how do you define success for yourself now?
23. Walk me through a time you had to be really brave.
24. Is there a dream you haven't given up on?
25. These days, how do you handle failure when it happens?
26. Which relationship has taught you the most?
27. Deep down, do you feel like you're living the life you wanted?
28. How has a loss changed the way you see things?
29. Which values would you never give up?
30. Share the story of a time you changed your mind about someone.
31. Are you where you thought you'd be at this age?
32. These days, how do you want people to feel after they spend time with you?
33. Which risk do you wish you'd taken?
34. Honestly, do you think people really change?
35. These days, how do you find meaning in ordinary days?
36. Which part of your life feels most unfinished?
37. I'd love to hear about a hard lesson that turned out to be a gift.
38. Is there someone you'd like to thank but haven't?
39. In your own words, how do you deal with feeling stuck?
40. Which part of yourself did you have to grow into?
41. Do you find it easy to ask for help?
42. How has your idea of happiness changed?
43. Which moment are you most grateful for?
44. Tell me about something you believed as a kid that you don't anymore.
45. Are there fears you've outgrown?
46. In your own words, how do you want to spend your time when you're older?
47. Which experience humbled you the most?
48. Do you think your work reflects who you really are?
49. In your own words, how do you keep going when things feel pointless?
50. Which kind of courage do you admire most in others?
51. Tell me about a choice that surprised everyone who knows you.
52. Is there a question you're still trying to answer about your life?
53. How do you want to be remembered by the people you work with?
54. Which part of your past are you at peace with now?
55. Do you feel understood by the people around you?
56. How has becoming an adult changed what you care about?
57. Which place feels most like you?
58. Tell me about a time you felt truly proud of yourself.
59. Are there things you wish you'd said to someone?
60. How do you know when to walk away from something?
61. Which lesson do you keep having to learn over and over?
62. Do you think you're kinder to others than to yourself?
63. How do you stay hopeful about the world?
64. Which person believed in you before you believed in yourself?
65. Tell me what you'd do with one more year of free time.
66. Is there a part of you that most people never see?
67. How have your friendships changed as you've grown?
68. Which moment made you feel like a real grown-up?
69. Do you ever feel like you're faking it?
70. How would your life be different if you'd stayed where you grew up?
71. Which of your beliefs came from hard experience?
72. Tell me about a time someone changed your life with one sentence.
73. Are you proud of how you handled a tough year?
74. How do you handle the fear of missing out on a different path?
75. Which part of your life would you want to live again?
76. Do you feel like you've found your purpose?
77. How do you want the next chapter of your life to start?
78. Which word describes this season of your life?
79. Tell me what gives you peace when things are loud.
80. Is there a goodbye that changed the direction of your life?
81. How do you show love to the people who matter most?
82. Which question would you ask your future self?
83. Who do you hope to become in the next ten years?

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