Questions to Ask a Guy | Free Conversation Cards Online

Light · 84 questions

Easy openers. Safe for anyone.

1. What's something you're good at that never comes up?
2. What did you want to be at eleven years old?
3. What's the last thing you got properly into?
4. Two days, nothing owed to anyone — what happens?
5. What's your most-worn item of clothing?
6. What sport or team could you talk about for an hour?
7. What's the best thing you've eaten this year?
8. What did your friends and you do for fun at seventeen?
9. What's a film you'd defend against anyone?
10. What's your worst habit that you're not planning to fix?
11. What's the last thing that made you laugh out loud alone?
12. What's the furthest you've travelled and why there?
13. What's your idea of a good Friday night now versus five years ago?
14. What are you saving up for?
15. What's the oddest way you've earned money?
16. What's something you own that you'd never replace?
17. What's a skill you'd learn if it took a week?
18. What music did you pretend not to like?
19. What's your go-to order anywhere?
20. What would you do with an extra hour every day?
21. Which video game from your childhood would you replay tonight?
22. How do you like your steak, or are you skipping it entirely?
23. If you could own any car for a week, which one?
24. Do you have a lucky jersey, hat, or pair of shoes?
25. Name the best burger you've ever eaten and where.
26. Which movie villain do you secretly root for?
27. How good are you at grilling, honestly?
28. Is there a band you've seen live more than once?
29. Which superhero would you actually want to be?
30. Would you rather go fishing at dawn or stargazing at midnight?
31. Pick a sport you'd go pro in if talent were free.
32. How many hours could you spend in a hardware store?
33. Which of your friends is the worst at directions?
34. Do you build things, fix things, or call someone?
35. Name a road trip you'd take with no plan at all.
36. If you had a boat, what would you name it?
37. Which gadget do you use every day without thinking?
38. How do you spend a rainy Saturday?
39. Is there a snack you always buy at gas stations?
40. Which cartoon did you race home to watch after school?
41. Would you rather have a home gym or a home theater?
42. Name the funniest prank you've pulled or fallen for.
43. How would you describe your cooking in one word?
44. Which city has the best food you've tried?
45. Do you have a signature move on the dance floor?
46. If you could be an expert at one outdoor skill, what would it be?
47. Which album do you know every word to?
48. How competitive are you at board games?
49. Is there a hobby you dropped that you want back?
50. Name the best pizza topping combo and defend it.
51. Which animal would make the coolest pet if rules didn't apply?
52. Would you rather climb a mountain or dive with sharks?
53. How do you pick a movie when nobody can decide?
54. Which job would you try for a day just for fun?
55. Do you prefer mornings on the trail or evenings on the couch?
56. Pick one decade of music to listen to forever.
57. Which celebrity would you want on your trivia team?
58. How do you take your coffee, if at all?
59. Is there a place you went as a kid that you'd love to revisit?
60. Name the most useless talent you have.
61. Which game night game do you always win?
62. Would you rather be famous for music or for sports?
63. How many cups of coffee is too many?
64. Which sports moment made you jump off the couch?
65. Do you keep a clean car or a lived-in one?
66. Name a food you refused as a kid but love now.
67. If you had a free plane ticket today, where are you going?
68. Which of your childhood nicknames stuck around longest?
69. How would you plan a perfect guys' weekend?
70. Is there a movie you've watched more than ten times?
71. Which season is your favorite, and what do you do in it?
72. Would you rather cook a feast or order everything on the menu?
73. Name the weirdest thing in your fridge right now.
74. How do you feel about camping: love it or tolerate it?
75. Which smell reminds you of your dad or grandfather?
76. Do you have a favorite spot to watch the game?
77. If you opened a bar, what would it be called?
78. Which fictional world would you want to live in?
79. How loud do you like your music in the car?
80. Is there a festival or event you'd love to go to?
81. Name a tool you think everyone should own.
82. Which comedian always cracks you up?
83. Would you rather have a cabin in the woods or a loft downtown?
84. How do you celebrate your birthday, usually?

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Deeper · 83 questions

Personal, but not heavy.

1. What are you actually working towards?
2. What's something you've changed your mind about?
3. Who taught you the most about being a man, and what did they get wrong?
4. What do you do when things go badly?
5. What gamble of yours actually worked out?
6. What's the worst stretch you've come out the other side of?
7. What kind of friendships do you keep, and why those?
8. What do people get wrong about you?
9. Where are you when you stop performing?
10. What's something you're not good at that bothers you?
11. What did you learn from your last relationship?
12. What makes you relax around someone new?
13. Which choice sent your life down a different road?
14. What are you proud of that isn't obvious?
15. What do you do when you can't fix something?
16. Who do you talk to when you're struggling?
17. Where's your line that nobody gets to move?
18. What's something you've had to unlearn?
19. What do you want your life to look like at fifty?
20. What's the last thing that genuinely moved you?
21. Which man in your life do you most want to be like?
22. When do you know you've earned someone's respect?
23. Is there a goal you've been quietly chasing for years?
24. Name something you've learned about yourself in the last year.
25. Which compliment actually gets through to you?
26. Do you find it hard to ask for help?
27. When you're burned out, what actually recharges you?
28. Which friend would you call at three in the morning?
29. Where do you feel most like yourself?
30. Is there a part of your job you truly love?
31. How has your idea of being a good man changed over time?
32. Which risk paid off in a way you didn't expect?
33. Name a moment you felt proud of how you handled something.
34. Do you think you show your feelings enough?
35. How do you handle it when someone doubts you?
36. Which of your values came straight from your parents?
37. Where do you want to be in ten years?
38. Is there a skill you wish your dad had taught you?
39. What does work pressure do to you?
40. Which of your friendships feels the most honest?
41. Name the best advice another man ever gave you.
42. Do you trust your instincts or overthink things?
43. What does affection look like coming from you?
44. Which fear have you already pushed through?
45. Where do you feel you're still figuring things out?
46. Is there a mistake that turned out to be a gift?
47. How do you like to be supported when life gets heavy?
48. Which of your qualities do you hope people notice?
49. Name a boundary you've set that made your life better.
50. Do you think you're easy to get to know?
51. How has a past relationship shaped the way you love now?
52. Which moment made you feel grown up?
53. Where do you go to clear your head?
54. Is there an opinion of yours that surprises people?
55. How do you feel about your relationship with your father?
56. Which dream from your teens do you still think about?
57. Name something that instantly makes you feel at home.
58. Small crew or big group of friends: which is you?
59. How do you celebrate your own wins?
60. Which area of your life needs more attention?
61. Where did you learn to be tough, and did it help?
62. Could there be someone you owe a thank you?
63. How do you know when you're genuinely happy?
64. Which mistake taught you the most?
65. Name what you look for in a partner.
66. Do you feel understood by your friends?
67. How did your first heartbreak change you?
68. Which part of your routine keeps you sane?
69. Where would you like more adventure in your life?
70. Is there a version of you from the past you're glad is gone?
71. How do you want your weekdays to feel?
72. Which person gives you the most honest feedback?
73. Name a cause that matters to you.
74. Do you tend to put yourself last?
75. When jealousy shows up, what do you do with it?
76. Which part of your life are you most proud of building?
77. Where does your time go that you'd like back?
78. Is there something you wish you'd started sooner?
79. How would your closest friends describe you?
80. Which of your goals scares you a bit?
81. Name a moment you stood up for someone.
82. Do you think you're hard on yourself?
83. How have your twenties or thirties surprised you?

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Deepest · 83 questions

The ones that stay with you.

1. When did isolation hit you hardest?
2. What do you never talk about?
3. What version of yourself would you hate to meet at fifty?
4. What have you never forgiven yourself for?
5. Who have you hurt, and does it still sit with you?
6. What did you need as a boy that you didn't get?
7. What do you carry that you've never put down?
8. When did you last cry, and what was it about?
9. What's the version of yourself you keep hidden?
10. What are you calling fine that isn't?
11. What do you want that you'd be embarrassed to say out loud?
12. What's heaviest about your life at the moment?
13. What would you change if nobody would be disappointed?
14. Who do you miss that you never mention?
15. What did you deny about yourself for far too long?
16. What do you think you'll regret?
17. When did someone last get you without explanation?
18. Whose opinion are you still working for?
19. What do you want to have meant to people?
20. What's the thing you'd say if you knew it wouldn't be held against you?
21. Which moment made you stop trusting people so easily?
22. How do you comfort yourself when nobody's watching?
23. Is there someone you still wish would say sorry?
24. Name the hardest goodbye you've ever had.
25. Which part of your story do you rarely share?
26. Do you ever feel like you have to prove your worth?
27. How did you learn to keep your feelings to yourself?
28. Which fear keeps showing up in your relationships?
29. Where have you had to be strong when you didn't feel it?
30. Could there be a younger version of you that you miss?
31. How would you want to be loved on your worst day?
32. Which relationship changed the way you see yourself?
33. Name the moment you felt most proud to be you.
34. Do you believe you deserve good things?
35. How has stress shown up in your body over the years?
36. Which words from your father still echo?
37. Where have you felt invisible?
38. Is there a choice you're still grieving?
39. How do you want to be remembered by your family?
40. Which dream have you never said out loud?
41. Name the moment you realized you'd outgrown a friendship.
42. Do you feel safe being fully honest with anyone?
43. How has losing someone shaped you?
44. Which of your walls do you wish someone would get past?
45. Where do you still need to heal?
46. Is there a promise to yourself that you broke?
47. How did your parents' marriage shape what you want?
48. Which small kindness from someone got you through a dark time?
49. Name what you'd tell your younger self about being a man.
50. Do you feel like people really know you?
51. How do you forgive someone who never admitted fault?
52. Which of your needs feels hardest to ask for?
53. Where does your loneliness hide?
54. Is there a friendship you still grieve?
55. How do you want your life to feel when you're old?
56. Which truth about your family did you figure out late?
57. Name the hardest thing you've accepted about yourself.
58. Do you ever feel like you're not allowed to struggle?
59. How have people let you down when it mattered?
60. Which part of you still wants someone to take care of you?
61. Where did you find strength you didn't know you had?
62. Is there a moment you'd relive just to feel it again?
63. How do you handle not being chosen?
64. Which dream would you chase if failure were impossible?
65. Name the kind of love you're afraid you won't find.
66. Has anyone ever fully heard you?
67. How do you hold onto hope when things fall apart?
68. Which person do you want next to you at the end?
69. Where have you been settling?
70. Is there a question you're afraid to ask yourself?
71. How will you know when you've made it?
72. Which part of your past still makes your choices?
73. Name the moment you felt the most alive.
74. Do you carry guilt about someone you left behind?
75. How would you want your future kids to know you?
76. Which fear of yours is the oldest?
77. Where do you need permission to slow down?
78. Is there a love you still think about?
79. How has being a man shaped what you're allowed to feel?
80. Which moment changed who you trust?
81. Name something you're still waiting to hear from someone.
82. Do you feel like you've become who you hoped to be?
83. How can someone earn your whole heart?

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