Deep Questions to Ask Your Friends | Free Cards Online

Light · 84 questions

Easy openers. Safe for anyone.

1. What's the best thing happening in your life right now?
2. What do you think we bonded over originally?
3. What's a memory of us you still bring up?
4. What's something you've started doing that you like about yourself?
5. What's the last thing that genuinely excited you?
6. What do you do now that would shock your teenage self?
7. What's a friendship you wish you'd kept?
8. What's something you'd like to do together that we never do?
9. What's your favorite thing about your life right now?
10. Who's your first call when everything goes sideways?
11. What's a place we should go together?
12. What's a hobby you'd take up with more time?
13. What's the best decision you've made this year?
14. What's something small that's been bothering you?
15. What's changed about you since we met?
16. What do people come to you for?
17. What's something you'd like to be known for?
18. What's the last book, show or song that got under your skin?
19. What's a version of your life you'd like to try for a year?
20. What's the next thing you're genuinely excited about?
21. Which of our friends would survive longest in a horror movie?
22. Who in our group is secretly the funniest?
23. Where would you go if we took a friends trip with no budget?
24. How would you describe our friendship to a stranger in one sentence?
25. If we started a band, what would we be called?
26. Describe your dream weekend with the whole crew.
27. Tell me the most embarrassing thing you remember about me.
28. Name a song that instantly reminds you of us.
29. Remember the first real conversation we ever had?
30. Would you rather go camping with me or on a cruise with me?
31. Is there a food you'll always associate with me?
32. Pick a movie we should watch together this month.
33. Which of my habits cracks you up the most?
34. Who would play you in a movie about your life?
35. Where's the best place we've ever hung out?
36. How did you spend your summers as a kid?
37. If you could master any skill by next week, what would it be?
38. Describe your ideal birthday party, no limits.
39. Tell me about the best meal you've had this year.
40. Name a guilty-pleasure show you'll defend forever.
41. Would you rather relive high school or college for a day?
42. Is there a trend you tried that you'd love to forget?
43. Pick the three people you'd want on a desert island.
44. Which app do you open way too often?
45. Who was your biggest celebrity crush growing up?
46. Where do you want to be on your next birthday?
47. How would your coworkers describe you?
48. If you had a free plane ticket today, where are you going?
49. Describe the weirdest job you've ever had or wanted.
50. Tell me a story you always tell at parties.
51. Name a place in this city everyone should visit once.
52. Would you rather have a personal chef or a personal driver?
53. Is there a hobby you've been meaning to try?
54. Pick a decade you'd love to have been a teenager in.
55. Which of us would be more likely to win a game show?
56. Who do you text the most, and about what?
57. Where did you want to live when you were little?
58. How do you recharge after a long week?
59. If our friendship had a slogan, what would it be?
60. Describe your perfect Saturday morning.
61. Tell me something that made you laugh this week.
62. Name an item you own that you'd grab in a fire.
63. Would you rather have a tiny house in the woods or a loft in the city?
64. Is there a band you'd drive five hours to see?
65. Pick a new tradition for our group to start.
66. Which chore do you secretly like doing?
67. Who in your family are you most like?
68. Where's the strangest place you've ever fallen asleep?
69. How many languages would you learn if it were free and instant?
70. If you could open any kind of shop, what would it sell?
71. Describe your comfort meal in delicious detail.
72. Tell me about a teacher you still remember.
73. Name the best gift you've ever received.
74. Would you rather go to a music festival or a quiet cabin with me?
75. Is there a rule you always break?
76. Pick the game night game you'd never play with me again.
77. Which of your friends would you trust with your phone?
78. Who's the best cook you know?
79. Where would you hide if you needed a day off from everything?
80. How would you spend a surprise day off tomorrow?
81. If you could be famous for one thing, what would it be?
82. Describe the moment you knew we'd be friends.
83. Tell me your hottest take about something harmless.
84. When did you last try something completely new?

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Deeper · 83 questions

Personal, but not heavy.

1. What do you think I don't know about your life right now?
2. When was the last time you felt genuinely low?
3. What's something you've been dealing with alone?
4. What do you need from your friends that you don't ask for?
5. What's a friendship that ended badly, and what did it teach you?
6. What do you think your biggest flaw is?
7. When do you feel lonely, even around people?
8. What's a decision you're second-guessing?
9. What's something you've outgrown but haven't let go of?
10. What do you think I get wrong about you?
11. What's a fear you have about the next few years?
12. When did you last feel proud of yourself?
13. What's a part of your family life you rarely talk about?
14. What's something you envy in other people?
15. What do you wish you were braver about?
16. What's the hardest thing you've been through since we've known each other?
17. What do you want your thirties, forties, whatever's next to look like?
18. What kind of support actually helps you?
19. What's a thing about you I've never thought to ask?
20. What do you think you're avoiding?
21. How do you want me to check on you when you go quiet?
22. Which of your friendships has changed the most over the years?
23. Where do you feel most like yourself these days?
24. Who has been the biggest influence on the person you are?
25. If you could redo one year of your life, which would it be?
26. Tell me about a moment you felt really supported by a friend.
27. Describe how your family handled hard feelings growing up.
28. Is there a goal you've been quietly working toward?
29. Would you tell me if I hurt your feelings?
30. Which part of adulthood caught you off guard?
31. How do you handle it when friends drift apart?
32. Where do you want to be in five years, honestly?
33. Who do you miss the most from a past chapter of your life?
34. If you could ask your parents one honest question, what would it be?
35. Tell me about a mistake that changed how you treat people.
36. Describe the kind of friend you're trying to be.
37. Is there a part of your life you feel stuck in?
38. Would you rather be respected or liked, and why?
39. Which compliment means the most to you?
40. How do you know when you need a break?
41. Where does your confidence come from, and where does it go?
42. Who is someone you've had to let go of?
43. If you had to start over somewhere new, what would you keep?
44. Tell me something you've never told our other friends.
45. Describe a time you felt out of place.
46. Is there anything you wish we talked about more?
47. Would you want me to be more honest with you, even when it stings?
48. Which of your worries do you think is unfair to yourself?
49. How has your idea of success changed?
50. Where do you feel pressure to be someone you're not?
51. Who do you go to when you need advice?
52. If you could change one thing about how you grew up, what would it be?
53. Tell me about a relationship that taught you a lot.
54. Describe a moment you surprised yourself with your own strength.
55. Is there someone you owe an apology to?
56. Would you say you're happy right now, on the whole?
57. Which of your habits are you trying to change?
58. How do you deal with jealousy between friends?
59. Where do you spend most of your emotional energy lately?
60. Who do you feel most responsible for?
61. If you could master one emotion, which would it be?
62. Tell me about the hardest goodbye you've had.
63. Describe what makes you feel appreciated.
64. Is there a dream you've quietly given up on?
65. Would you want to know if I ever felt left out by you?
66. Which of your beliefs has changed the most since we met?
67. How do you want to be supported when things go wrong?
68. Where do you feel you've grown the most this year?
69. Who in your life brings out your best?
70. If you could say something to your sixteen-year-old self, what would it be?
71. Tell me about a time you felt misunderstood by everyone.
72. Describe what home means to you now.
73. Is there a friendship you're afraid of losing?
74. Would you ever move far away, even if it meant leaving us?
75. Which part of your job do you actually love?
76. How do you usually hide when you're struggling?
77. Where did your sense of right and wrong come from?
78. Who do you compare yourself to the most?
79. If you could spend a day with anyone who has passed away, who would it be?
80. Tell me about something you're quietly proud of.
81. Describe the best advice a friend ever gave you.
82. Is there a question you've always wanted to ask me?
83. Would you tell me if you thought I was making a big mistake?

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Deepest · 83 questions

The ones that stay with you.

1. What's the loneliest period of your life been?
2. What do you carry from your childhood that still shapes you?
3. What's something you've never forgiven yourself for?
4. Who has hurt you most, and have you told them?
5. What do you think people would be surprised to know about you?
6. What's a version of yourself you're afraid of becoming?
7. What are you grieving that nobody knows about?
8. What's the hardest truth you've had to accept?
9. When did someone last really get you without you explaining?
10. What do you want that you feel you don't deserve?
11. What's something you'd want said at your funeral that isn't true yet?
12. What's the closest you've come to giving up?
13. What do you need to hear from someone, and from who?
14. What's a relationship you're staying in out of fear?
15. What have you lied about for so long it feels true?
16. What do you want to have healed by the end of this decade?
17. If you could tell one person one thing with no consequences, who and what?
18. What do you think your life is for?
19. What would you change if nobody would be disappointed in you?
20. What do you hope I'd do if you fell apart?
21. How do you want your friends to show up if you ever lose everything?
22. Which of your fears have you never said out loud?
23. Where did you feel most abandoned in your life?
24. Who do you wish had loved you better?
25. If you could undo one choice, which would it be?
26. Tell me about the darkest moment you've climbed out of.
27. Describe the part of yourself you hide from everyone, including me.
28. Is there anyone you've never forgiven?
29. Would you tell me if you felt like giving up?
30. Which loss still shapes how you live?
31. How do you really feel about the way your life turned out so far?
32. Where do you feel unworthy of the people who love you?
33. Who knows the real you, fully?
34. If you died tomorrow, what would you regret not telling me?
35. Tell me about something you did that you've never made peace with.
36. Describe a time you felt completely alone in a room full of friends.
37. Is there a secret you've kept for too long?
38. Would you let me help if you were really struggling?
39. Which of your relationships has hurt you most deeply?
40. How do you want to be remembered by your friends?
41. Where does your deepest sadness come from?
42. Who would you most want at your side if you were dying?
43. If you could hear one thing from your parents, what would it be?
44. Tell me what you're most afraid of losing.
45. Describe the moment you felt like your life was falling apart.
46. Is there a part of your childhood you wish you could rewrite?
47. Would you ever tell me if you were thinking of leaving everything behind?
48. Which apology are you still waiting for?
49. How have you changed after your worst heartbreak?
50. Where do you think you'll feel most at peace at the end?
51. Who have you let down in a way you think about often?
52. If you could be completely honest with one person, who would it be?
53. Tell me about a moment you felt unlovable.
54. Describe the thing you need most but rarely get.
55. Is there something about your past you're ashamed of?
56. Would you want me to push you when you're shutting everyone out?
57. Which of your dreams scares you because it matters so much?
58. How do you want to be cared for when you're grieving?
59. Where did you learn to carry everything by yourself?
60. Who would you forgive today if you could?
61. If you knew you had one year left, how would you spend it?
62. Tell me about the loneliest birthday you've had.
63. Describe what you'd want from me on the worst day of your life.
64. Is there a relationship you ended that you wish you hadn't?
65. Would you tell me the truth about how you're really doing?
66. Which part of your story have you never shared with anyone?
67. How do you want our friendship to look when we're very old?
68. Where do you still feel like a child?
69. Who made you feel small, and do you still hear their voice?
70. If you could let go of one burden right now, which would it be?
71. Tell me what you've needed from friends but never asked for.
72. Describe a time you felt truly saved by someone.
73. Is there something you'd want me to do for you if you couldn't ask?
74. Would you ever want to repair a friendship you've lost?
75. Which memory makes you feel the most grateful to be alive?
76. How do you cope when nothing seems to help?
77. Where do you hope your life ends up, deep down?
78. Who do you worry about most at night?
79. If our friendship ended, what would you miss most?
80. Tell me what you think you're here to do.
81. Describe the kind of love you want to leave behind.
82. Is there a question you're afraid I'll ask you?
83. Would you still be my friend if you knew everything about me?

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