50 Non-Basic Questions To Ask Your Date If You Actually Want To Have A Memorable Time

1. What is something that makes you laugh that isn’t actually that funny?

2. What’s the go-to movie or tv show you watch when you’re sick?

3. If you could go back in time and pick up any sport or hobby as a young kid, what would it be?

4. If you had to pick any person in Hollywood to be our president starting tomorrow, who would you choose?

5. What’s the first thing you need in the morning when you’re hungover?

6. If all of your money had to go to one single cause when you died, what would you choose?

7. What’s your favorite ‘worst’ tv show of all time?

8. What’s your biggest pet peeve on an airplane?

9. What’s the hardest you’ve ever laughed in a situation where it was extremely inappropriate to do so?

10. Who is a celebrity that most people thoroughly dislike that you respect?

11. When medical tv shows show the surgeries/injuries/gooey stuff – do you look away instantly or watch in fascination?

12. What’s your favorite movie quote?

13. If your friends want you to go out and you refuse to rally, what’s the one song they can play that will change your mind?

14. What was your favorite class in college that had nothing to do with your major?

15. What was the best road trip you’ve ever been on?

16. What do you think really happens at the end of Inception? 

17. Who’s your favorite Disney cartoon character?

18. What is the most scared you’ve ever been?

19. Would you rather be unbearably hot or unbearably cold?

20. In your opinion, what is the most annoying word in the English language, a la “moist”?

21. Which of your friends have you known the longest?

22. If you could have lunch with any living person in the world, famous or not, who would it be?

23. If you could have lunch with any deceased person, famous or not, who would it be?

24. What’s the longest nonstop plane ride you would ever be willing to take?

25. Have you ever teared up from a commercial?

26. Which of your friends makes you laugh the hardest?

27. What’s something totally ordinary that makes you inexplicably anxious?

28. What’s your favorite holiday movie?

29. Are there any alcoholic drinks or drink combos that make you feel instantly nauseous because of bad memories?

30. What’s your favorite meme of all time?

31. Do you have a tell when you don’t like someone?

32. What’s something most people are afraid of that doesn’t affect you at all?

33. What’s your go-to comfort outfit after a shitty day?

34. What’s your go-to comfort food after a shitty day?

35. If you could save one possession from a fire, what would it be?

36. Do you say ‘bless you’ to strangers?

37. What was your go-to hangout spot in high school?

38.If you could only watch one movie for the rest of your life, what would you choose?

39. What’s the funniest gift you ever asked for as a kid?

40. What’s a career that’s the complete opposite of yours that you would switch to in an instant?

41. What is your go-to tv show when you can’t fall asleep?

42. What was the worst outfit you’ve ever worn that you used to think you looked like hot shit in?

43. Do you sleep better when your nice and warm or super cool?

44. If you could avoid any chore for the rest of your life what would it be/

45. What got you in trouble the most as a kid?

46. Which movie do you know the most quotes from, word for word?

47. What’s the best season transition?

48. Which actor or actress currently under 40 could you see eventually becoming the greatest talent of our generation?

49. Who is one long-lost friend that you wish you could reconnect with?

50. What’s the hardest thing about adulthood?