Thought Catalog

30 Fun Questions To Ask On A First Date That Start Conversation And Keep It Going

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1. If you could invite five people, dead or alive, to a dinner party, who would you choose and why?

2. When you were little, where did you think you’d be by now? Are you there?

3. What was the last dream you had?

4. If you could start a band, what kind would it be and would you name it?

5. Were Ross and Rachel on a break?

6. What was the first album you bought, and why did you buy it?

7. It’s your 75th birthday. Where do you see yourself?

8. What is your favorite mistake?

9. Who do you look up to of the same sex?

10. Who is your role model of the opposite sex?

11. It’s New York City in the 1920’s. What are you doing?

12. What is your favorite book?

13. What is your guilty pleasure song?

14. What was a situation that you initially thought was terrible, but ended up being a blessing in disguise?

15. What’s your favorite word?

16. If you could choose a decade to grow up in, which would you choose?

17. What was your first concert?

18. The stupidest thing you’ve ever spent money on?

19. What would your superpower be?

20. And your superhero name?

21. If you could live in any city, which would you choose? Why?

22. Could you spend a day without your phone?

23. What about a week?

24. The Rolling Stones or the Beatles?

25. If you could be a type of beer, which would you be? Why?

26. If you could live in any fantasy world, be it Hogwarts or Narnia, where would you choose? Why?

27. What is the last book you read? Did you like it?

28. If you could have any talent, which would you have?

29. What was your AIM screenname? Why did you choose it?

30. Would you like to go out again next week?
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