15 Questions You Should Never Ask on a First Date

Are you about to go on a first date and looking for great tips on conversation starters?

Do you feel like you are stuck  and not sure how to break the ice in order to start a conversation?

Maybe you are trying to plan ahead by having several questions in reserve just in case the question you had planned to use a conversation starter fizzled out.  If those are the cases, then you’re in the right place, because I’ve got you covered!

You might feel excited and nervous, or maybe both! I know, I’ve been there.  It’s  a totally normal feeling when you are on a first date! But what’s important to remember is that first dates don’t have to be stressful and one of the best ways to alleviate your anxiety related to first dates is to have some kind of plan in place.

I’m not saying that you should write these questions on index cards and rehearse them,  but a solid technique to increase the chances of date going well.  

To help alleviate these stresses,  I’ve compiled this list of great first date conversation starters for you to save you from those long pauses and awkward silences that can and may happen on your date. 


Creative and Fun First Date Conversation Starters

1. What is your favorite memory?

2. If you had off from work today, what would you do?

3. What was the last thing that made you laugh?

4. Who (or what) gives you the most motivation?

5. Do you believe in fate or free will?

6. Do you prefer crosswords or word searches?

7. Is there a film that changed your entire outlook on life?

8. What’s the most fascinating random fact you know?

9. Is there any motivational speech from a celebrity that sticks out in your mind?

10. What genre of books do you prefer?

Creative and Fun First Date Conversation Starters

11. Do you enjoy films with subtitles?

12. What color of pen do you prefer writing in?

13. What is your favorite roller coaster you have ever ridden?

14. Has a pickup line ever worked on you?

15. Do you consider yourself an old soul?

16. Which song lyrics speaks to you the most?

17. What phrase did you once used ironically, but has now become a part of your vocabulary?

18. Do you prefer to type or write with a pen?

19. What television or movie character do you feel a bond with?

20. Which invention would be impossible to live without?

Creative and Fun First Date Conversation Starters

21. What was the most interesting documentary you’ve ever seen?

22. What do you think the most impressive thing about the universe is?

23. Which one of the five senses do you deem most important?

24. What was the most stimulating discussion you’ve ever had?

25. Would you rather explore space or the deep sea?

26. What is the craziest thing you’ve ever done?

27. Would you have a conversation with a stranger?

28. Where is one place you feel most like yourself?

29. Where is your favorite place to escape to?

30. Who do you think has had the largest influence on the person you are today?

Creative and Fun First Date Conversation Starters


31. When you were younger, what did you think you were going to be when you grew up?

32. If you could identify with one fictional character (from a book, show, or movie) who would it be?

33. Do you easily accept compliments? Or do you hate compliments?

34. What is your favorite non-physical attribute about yourself?

35. What’s one thing you’d love to learn more about?

36. What is something you’ve never done that you’ve always wanted to do?

37. What’s your favorite joke?

38. If you could be any animal, what animal would you be?

39. If you could go back to any age or time of your life, what age or time would it be?

40. What’s one thing you would say that makes you unique from other people?

41. What’s your favorite inspirational quote?

42. Who is the smartest person you’ve ever met?

43. What’s your favorite TED Talk of all time?

44. Which newspaper (or website) do you get your news from?

45. If you competed on a game show, which charity would you play for?

46. What is the last thing you wrote by hand instead of typed?

47. Which song do you always end up playing during long drives?

48. Which romantic gesture do you believe is overrated?

49. What small act of kindness do you believe is underrated?

50. What is the one compliment that people always seem to give you?


51. When was the last time you complimented a complete stranger?

52. Which pet name do you find the cutest (sweetie, honey, babe, etc.)?

53. Where do you escape to when you want peace and quiet?

54. Do you feel comfortable in silence?

55. Do you consider yourself a romantic or a skeptic?

56. What is the kindest thing another person has ever done for you?

57. What is the most surprising item on your bucket list?

58. Which season do you look forward to all year long?

59. Would you rather live in one place for a very long time or live in many places and move around?

60. Do you like movies that make you cry? Or do you avoid them?

>>Act Like a Lady, Think Like a Man: What Men Really Think About Love, Relationships, Intimacy, and Commitment<<

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Creative and Fun First Date Conversation Starters

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Author: Rosanna Lundberg

I am passionate about helping women design their dream LIFE one goal at a time and manifest their dream LOVE one date at a time.

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