36 Questions To Give Your First Date The Third Degree


First dates are the worst. After going through the trouble of finding someone to spend time with, sifting through your wardrobe for a reasonable outfit, and scouring Yelp for a restaurant that’s cheap yet chic, you still have to actually GO to the thing. However, the worst part of a first encounter with a potential love interest is the monotonous small talk necessary to break the ice.

But how do you skip the “So, where did you grow up?” talk with someone you hardly know? You’ve probably read the New York Times 36 questions to make someone fall in love with you, but what if you just want your date to fall in like with you? Here are some ice breaker questions that’ll get your relationship to a place even Goldilocks would approve of:not too hot, not too cold, but just right.

1. What do you rely on?
2. Do you prefer shopping alone or with other people?
3. Have you ever journaled?
4. If yes, what kind of journal do you keep?
5. If no, do you want to?
6. If you want to journal, what’s keeping you?
7. If you don’t want to journal, why not?
8. Do you think more with your hands or your mind?
9. What’s the dumbest thing you’ve ever done on an impulse?
10. Name a word you mispronounced/misspelled/misused for several years. How did you identify your mistake?
11. What do kids these days just not understand?
12. What did you do when you were their age?
13. If you could live on Mars, would you? Why or why not?
14. What do you do when you just can’t sleep?
15. What’s your favorite book?
16. What’s your least favorite book?
17. What’s a book you pretend you’ve read but you actually haven’t?
18. What’s a book you’ve always wanted to pick up but you’ve never had the chance to read? Explain.
19. If you had to write a book, what would it be about?
20. Would it be fiction or nonfiction?
21. What would the cover of your book look like?
22. What would the title of your book be?
23. Where would your book be sold?
24. When people ask, “How are you?”, what is your go-to response?
25. What’s the hardest goodbye you’ve ever had to say?
26. Do you utilize read receipts? Why or why not?
27. Do you have a dream partner? Do you believe they exist?
28. Did you smoke weed in high school? Why or why not?
29. Did you have a fake ID in high school?
30. If yes, what state was it from? What was your name? Birthdate? Address?
31. If no, did you ever have a false identity in any other sense of the phrase?
32. If you could do absolutely anything, what would you do?
33. What do you think about people who don’t believe in global warming?
34. Name your irrational fears.
35. Name your rational fears.
36. What’s the luckiest thing that’s ever happened to you?