First Date Questions

Generally speaking, first dates make people nervous…

According to a study published by the New York Post, a first date should last a little under three hours (2.72). The same study also notes that it takes people about four dates to feel comfortable with another person. Almost one-third (31%) of respondents feel the least comfortable part about going on a first date is the nerves.

So…what are you supposed to say in that 2.72 hour date, four dates before you feel fully comfortable with the stranger across from you with nerves running rampant?

To help facilitate conversation, we’ve compiled what we consider to be the best icebreaker questions for a first date! Not too personal, not too out of left field, but just enough to get the ball rolling and help your personality to start shining through.

So dive on into our list of the very best first date questions. And (as always) we extend to you a warm Chatterbox invitation to upvote your favorites.

  1. What is the most trivial thing about which you have a strong opinion?
  2. What is your favorite activity that doesn’t cost any money?
  3. How much would someone have to pay you to be on the bachelor / the bachelorette?
  4. What group size are you most at ease in?
  5. What is something you really resent having to pay for?
  6. If you woke up in the body of someone of the opposite gender, what would you be interested to find out or do?
  7. You have $10m USD but you can only buy things that start with the first letter of your name. What do you buy?
  8. Would you rather have the ability to see ten minutes in the future or 150 years in the future?
  9. What is one thing you’re good at that people don’t expect?
  10. What is the smallest thing for which you are grateful?
  11. What is something you’ve done/felt/seen/etc. that you wish you could experience again for the first time?
  12. If you could magically make one food or habit healthy, what would you choose?
  13. At a party, where can someone find you?
  14. If you had to award yourself a superlative in high school what would it be?
  15. What about life 100 years ago appeals most to you?
  16. If you could be a part of any TV family which would you choose?
  17. Which Winter (or Summer) Olympics event do you think you’d have the best chance at competing in?
  18. What do you respect most about your best friend?
  19. What do you think you do better than 90% of people?
  20. If you could send a one-sentence-message-in-a-bottle to yourself from ten years ago what would it be?
  21. What do you get the most compliments about?
  22. What is a childhood habit or preference that you’ll never outgrow?
  23. Ideally, how would you spend your birthday?
  24. What profession do you think you would be the least happy in?
  25. What is your best trivia category?
  26. Describe your perfect day. Option 1) You are restrained to 24 hours, but you can transport yourself to anywhere in the world. Option 2) Your realistic perfect 24 hours.
  27. If you could develop any one athletic skill overnight what would it be?
  28. What is something you’ve done / felt / seen / etc that you wish you could experience again for the first time?
  29. What is your favorite emotional attribute you inherited from your parents? What is your favorite physical attribute you inherited from your parents?
  30. What is the luckiest thing that has happened to you? What is the unluckiest thing that has happened to you?
  31. In a “Freaky Friday” situation where you woke up in someone else’s body, who would you like to be for a day and have them inhabit your body?
  32. Do you think you are an above or below average dancer? Do you think you are an above or below average singer?
  33. Generally speaking, are you someone who lives more in the past, present, or future?
  34. In what way do you consider yourself unique? (You can’t opt out by saying you aren’t unique)
  35. Has anything happened in your life that you felt severely underprepared for?
  36. What physical traits do you share with your relatives? Personality traits?
  37. Is there something about you that people assume because of your appearance or demeanor? What is a trait or preference you have that people don’t expect you to have?
  38. What’s the biggest difference between you and your family?
  39. What one value defines your family the most?
  40. What conspiracy theory if true would shock you the most?
  41. Is there a historical event that you lived through that is now a core memory for you?
  42. Are there any political issues where you still find yourself wavering?
  43. What do you regret not sticking to or starting when you were younger?
  44. If you had to eat at one restaurant for the rest of your life which would it be?
  45. What physical traits do you share with your relatives?
  46. What is your favorite app?
  47. What board game (or game generally) are you the worst at?
  48. How many pairs of shoes is too many to own? At what point does it become excessive?
  49. What should be taught in schools but isn’t?
  50. How do you approach consuming news / current events?
  51. What is your love language? Do you think about love languages when you are in a relationship or are they not something you place a lot of value on?
  52. What is your favorite household chore? What is your least favorite?
  53. What is your favorite purchase you have made in the last year?
  54. If you had to pick one friend to make all your decisions for you, who would it be?
  55. If you could have one mystery solved which would you choose?
  56. Have you ever been told that you have a doppelgänger? If so, who is it?
  57. If you had to attend a college different than the one you did, where would you have chosen?
  58. What is the most ordinary-seeming thing that you find fascinating?
  59. What do you know isn’t real, but want badly for it to exist?
  60. What about dating norms do you think is outdated?