50 Things You Should Ask A Girl When She Gives You A Free Pass To Ask Anything


So you’ve met this girl who thinks really big thoughts, and she’s become your favourite place to go in your daydreams.

You’ll want to ask her zillions of questions, from all the profound existential nonsense that’s bugging us year round, up to her favourite ketchup brand.

You won’t want to go for tacky, same as you won’t want to go for the obvious, malicious curiosities such as how many people she slept with or how much she likes you on a scale 1 to 10, because these are things you might not even want or need to know in order to keep pursuing her.

1. What’s the worst thing to say on a first date?

2. What’s better, having high expectations or having low expectations?

3. What kind of old person do you want to grow up to become?

4. What was your worst job?

5. What qualities do you value most in a friend?

6. If you could invent a holiday, what would it be?

7. Are you smarter than your parents?

8. What’s the nicest thing about you?

9. What is your biggest fear?

10. If you died tomorrow, how would you like to be remembered?

11. What’s the craziest thing you’ve ever said out loud?

12. What is your favourite TV character from childhood?

13. What do you expect in a significant other?

14. What’s the hardest thing about modern dating for you?

13. Would you go on a space mission to repopulate a different planet? What would you take with you?

14. What is feminism to you?

13. What would you do if you inherited 1 million $ tomorrow?

14. Tell me your craziest food fantasy.

15. Why do you think people mistake hormones for love?

16. Have you ever been in a fight?

17. What is the best way to make you feel better on a sad day?

18. What is your relationship with your mother?

19. What is your biggest political worry and what would you feel the world should do differently about it?

20. What are your feelings on death penalty?

21. How many times have you been in love?

22. What is your opinion on fries with caramel ice cream?

23. Have you ever done something really bad or illegal?

24. Would you crash a wedding with me?

25. Have you ever fallen in love with a movie or book character?

26. What is your favourite childhood memory?

27. Have you ever felt abused by a person or system?

28. What would you do if you ended up on a secluded island with me?

29. Can you give me some tips on pleasing a woman sexually?

30. What was the most challenging moment of you career?

31. What would you think of me if I told you I was bisexual?

32. Do you want to have children?

33. What is your favourite thing about science and physics?

34. How do you feel about the idea that we can’t love just one person throughout our lives?

35. Alternatively, how do you feel about monogamy vs. polyamory?

36. What is the best thing someone ever said to you?

37. What is the most intense sexual experience you’ve had?

38. What would you advise me to do if I was not over my ex?

39. Do you find psychology useful?

40. Would you reject someone based on their looks?

41. Would you marry someone much younger/older than you?

42. What’s the creepiest thing about you?

43. Why do you think birds fly in a circle above tall buildings?

44. What are your views on cultural appropriation?

45. What do you dream about at night and how do you explain it?

46. What’s the most reckless thing you’ve done?

47. Would you kiss a complete stranger without having even spoken to them before?

48. Do you believe in reincarnation?

49. Have you ever ghosted someone/been ghosted?

50. What is your dream?