1. If you had to leave the country tomorrow and could only bring one suitcase, what would you put in it?
2. What do you never procrastinate doing?
3. If you had a choice to either feel no fear or feel no pain for the rest of your life, which would you choose?
4. Would you rather be overweight but amazing at sex, or thin but mediocre at sex?
5. If you had the chance to relive the last 5 years of your life, what exactly would you do differently?
6. What fantasy do you play in your head as you listen to music and walk down the street?
7. What is the best feeling that you experience in your day? Describe what you’re doing when you feel it.
8. If someone gave you a budget of $50,000 and let you take a year off of work, what would you do with that time?
9. What do you think is the biggest mistake your parents made?
10. What is something that you know will potentially shorten your life, but you keep doing anyway?
11. What is your favorite sexual memory of us?
12. What is one way in which you are aware that you aren’t living up to your full potential?
13. What’s one goal you have for this year, and what has held you back from accomplishing it so far?
14. If you knew that you were going to be deployed to war in one month, what would you do today?
15. Would you prefer to change your past or control your future?
16. What is something that everyone in the world could stand to realize?
17. Is that also something you could stand to take your own advice on?
18. What made your hardest breakup so painful?
19. Describe a day in your life 3 years ago. What was it like?
20. If you had to choose a specific daily routine that you would live on repeat every day for the rest of your life, what would it be?
21. What is something that you think most major religions do wrong?
22. What is something that you think most major religions do right?
23. When you’re falling in love with someone, what physical sensations do you feel in your body/chest?
24. What’s one thing that you hope everyone thinks about you?
25. What’s one thing you fear everyone thinks about you?
26. Do you believe suffering has a purpose?
27. Have you ever had a supernatural experience you couldn’t rationally explain?
28. If you could wake up tomorrow having acquired mastery in one specific skill, what would it be?
29. What is something that you wish came easier for you?
30. What is something that you worry about irrationally?
31. Who is the person who hurt you most in your life?
32. What did they also teach you?
33. What are the three things you have failed at in the past?
34. What have you learned from each of them?
35. Where is your “spiritual home?” Perhaps not the place you were raised, but where you feel most yourself, and like you belong?
36. What’s something that you think people wouldn’t judge you for if they understood why you behaved the way you did?
37. If you had to spend a Saturday night by yourself, what would you do?
38. What’s something simple that makes you really happy?
39. What was something in your life that you swore you would never get over?
40. How did you?
41. What’s one thing you want to do that scares you?
42. What’s the one thing you’ve learned from your past relationships?
43. Do you ever rehearse conversations by yourself before you have them? Why?
44. If you could only ever hangout with four people for the rest of your life, who would you choose?
45. Would you rather be surrounded by people and having usual conversation, or by yourself and reading something mind-blowing?
46. Why do you think relationships fail so often?
47. If at the end of your life, you met the person you could have been, would you be happy with who you’re currently becoming?
Get your copy of Brianna Wiest’s book, 101 Essays That Will Change The Way You Think, here.