1. Are you young at heart, or an old soul?
2. What makes someone a best friend?
3. What Christmas (or Hanukkah) present do you remember the most?
4. Tell me about a movie/song/tv show/play/book that has changed your life.
5. Name one physical feature that you like about yourself, and one you dislike.
6. Would you like to reconnect with any friends you’ve lost contact with?
7. What’s more important in a relationship: physical attraction or emotional connection?
8. Name a movie that you knew would be terrible just from reading the title.
9. What holiday do you most look forward to?
10. How is the relationship between you and your parents?
11. You’ve got the TV on, but you’re not really watching. What channel is the TV on?
12. Name a song that never fails to make you happy.
13. You know at least one person named Michael. Tell me about him.
14. Have you ever read the “missed connections” on Craigslist? Have you ever posted one, or wanted to?
15. If you could pick anywhere to live the rest of your life, where would it be?
16. Can money buy happiness?
17. Do you drink? Smoke? Do drugs? Why, or why not?
18. Is there anyone close to you that you know you can’t trust? You don’t have to give names.
19. Where was your favorite place to go when you were a little kid?
20. Have you ever spent a night in the hospital?
21. Do you enjoy being with only one or two friends, or with a large group of people?
22. Do you like the type of music your parents listen to? Do your parents like the type of music you listen to?
23. Have you ever been bullied? Have you ever bullied anyone else?
24. If you could only eat one thing for the rest of your life, what would it be?
25. If your partner wanted to wait until marriage before having sex, would you stay in that relationship?
26. Do you believe in a god?
27. Of all the social networks in the world, why use Tumblr?
28. What’s your favorite Tumblr tag to track?
29. Would you call yourself/your family “middle class?”
30. Name a TV series you didn’t enjoy until after it ended.
31. Have you ever bought a product from an infomercial?
32. If you could give up your car and never have to drive again, would you?
33. If you go back to one point in time to give advice to yourself, when would you go and what would you say?
34. What’s your “quirkiest” habit?
35. What is “normal?” Are you normal?
36. Someone close to you is dying. You have the choice to let this person live for 10 more years, but if you do, you cause the death of 10 strangers. You don’t have to see them die. Do you take the offer?
37. What is one thing you could never forgive?
38. Would you rather be in a relationship after the honeymoon period ends, or be single?
39. Is it possible for guys and girls to be just friends?
40. Where do you and your friends go to hang out?
41. Write the first paragraph of your obituary.
42. What is the best TV theme song ever?
43. When you were young, what would you dream you would be when you grew up?
44. When you’re alone in your own home, do you walk around naked?
45. What gets you out of bed in the morning?
46. Do you want to have more friends than you have right now?
47. What part of the past year sticks out in your mind?
48. You win a scratch-off lottery game that gives you $2000 a week (after taxes) for the rest of your life. Do you keep your job?
49. Could you be in a long-distance relationship? If you’re in one, what makes yours work?
50. What’s the best route to your heart?
51. Have you ever met someone through the internet, then met them in real life?
52. What is your favorite sport?
53. What has been troubling you lately?
54. Did you enjoy your high school prom? If you haven’t gotten there yet, do you look forward to it? If you didn’t go, why not?
55. What do you use more often: your intuition or logical reasoning?
56. Do you know what makes you happy?
57. Tell me about the last book you read.
58. What is the nicest compliment you’ve ever been given?
59. Who was your first crush?
60. Do you believe that there is life on other planets?
61. Predict what your life will look like a year from now.
62. Often, people will ask how your last relationship ended. I want to know how it began.
63. Where is your favorite place to go out and eat?
64. What is something you want to change about your current situation?
65. Early bird or night owl?
66. Are there any childhood possessions you still hold on to?
67. Give me an unpopular opinion you have.
68. What was the last song that was stuck in your head?
69. Where do you live? Be as general or specific as you want.
70. Do you believe in giving kids medals and trophies for participation?
71. What was the longest car ride you’ve ever taken?
72. Have you ever taken part in a protest?
73. Would you ever use an online dating service?
74. What is your ethnic heritage?
75. Describe a person that inspires you.
76. If you earn minimum wage doing what you love, would you?
77. Do you believe in luck?
78. Describe the last time you were very angry at someone.
79. Do you want to live until you’re 100?
80. Do people change? If so, how do you keep a relationship together when both of you start to change?
81. Have you ever risked a friendship by telling someone you liked them?
82. Would you rather be alone doing something you enjoy, or doing something you don’t like with your best friends?
83. Do you practice what you preach?
84. If you take precautions to stay safe, do you ultimately act more recklessly?
85. What do you value more in a significant other: Attractiveness or intelligence?
86. Are you hard-headed?
87. Have you ever laughed uncontrollably when it was socially inappropriate?
88. When have you felt most alive?
89. Would you prefer to live? A city? The suburbs? The countryside? The mountains?
90. Do you often skip breakfast?
91. How do you know what true love is?
92. Would you want to know the exact date and time you were going to die?
93. Where is “home” for you?
94. What song best describes your life right now?
95. Do you want to be perfect?
96. What have you never tried, but would really like to someday? What’s holding you back?
97. How do you express your creativity?
98. Describe your neighborhood.
99. Name something you only liked because it was popular.
100. Give me the story of your life in six words.