75 First Date Questions That Are Actually Interesting

Stacy KarynFirst Date, General Dating Advice4 Comments

Whether you are new to singlehood or a seasoned dating expert, it can sometimes be tricky to come up with interesting questions to ask your dates. And yes, sometimes you’ll click like crazy, sending the conversation into a rapid exchange filled with what feels like fireworks. But not every date is going to be like this. Sometimes it’s just nice to have some first date questions on hand and ready to use.  

So, how should you use this list? Well, your date should actually be more of a natural exchange of ideas. It shouldn’t be scripted. Your questions should be genuine and spontaneous. But it’s good to keep some back-up questions on hand for those cases of awkward silences. So before your next date, go through the following questions and pick out six that you like. Write them down and go through them out loud. This will help you memorize them. You’ll really only need six at a time, as it’s pretty unlikely that you’ll go through six awkward silences over the course of one date.

Then, on your date, as soon as you feel that awkward silence coming on, grab one of your questions and keep the conversation going. Easy as that! And by the way, this list works wonders for spicing up relationships too, old and new!

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75 First Date Questions That Are Actually Interesting


1. Where is your family originally from?
2. Have you always lived in (current city)?
3. Have you ever taken one of those DNA ancestry tests?
4. Does anyone in your family keep track of your family tree?
5. How many siblings do you have?
6. Do you have a big family?
7. Who are you closest to in your family?
8. Does your whole family live in (current city)?
9. Do you get along with your brothers/sisters?
10. Do you want to have a big family of your own one day?


11. What do you do for a living?
12. What’s your dream job? Or are you already doing it?
13. Where do you hope to be in 5/10 years?
14. What do you love about your job?
15. Do you get along with your coworkers?
16. Is your job stressful?
17. Can you tell me more about what you do?
18. What made you decide to get into this field?
19. What did you study?
20. Would you ever consider going back to school?


21. Do you play any sports?
22. Have you ever tried meditation?
23. How do you usually spend your days off?
24. What would you say is your biggest passion?
25. Have you ever tried (insert one of your own favorite hobbies here)?
26. Are you a sports fan?
27. Do you ever end up binge watching anything?
28. Can you sing or play any instruments?

Hypothetical Questions

29. If you could learn any new skill overnight, what would you learn?
30. If you had more time, what would you do with it?
31. If you could live anywhere in the world, where would it be?
32. If you could trade lives with anyone for a day, who would you trade with?
33. If you could choose, what would be your last meal on earth?

The Past

34. What were you like as a child?
35. What would you say was the best day of your life so far?
36. What do you think 9-year-old you would be pissed about when looking in on your life now?
37. What’s the worst job you’ve ever had?
38. What’s your biggest regret?
39. Did you ever go to summer camp as a kid?
40. Were you in girl/boy scouts?
41. Who was your teenage crush?


42. Do you like to travel?
43. Where have you traveled to so far?
44. Is there anywhere you would never visit?
45. Is there anywhere you would never return to?
46. Where do you hope to travel to next?
47. Do you have a bucket list?
48. What’s on your bucket list?


49. Do you have any pets?
50. Are you a cat person or a dog person?
51. Do you live on your own?
52. Do you have roommates? / Have you ever had roommates?
53. Did you move a lot growing up?
54. Do you like where you live?
55. What would your dream house look like?


56. Are you a morning person?
57. Do you believe in soulmates?
58. What’s your biggest fear?
59. Would you rather be rich or famous?
60. Do you consider yourself more of an introvert or extrovert?
61. Do you know your Myers-Briggs type?
62. Are you allergic to anything?
63. If you could change anything about yourself, what would you change?


64. Do you have a lot of close friends that live here?
65. Who are you closest to?
66. Do you have any nicknames?
67. What’s the best advice anyone has ever given you?
68. What was the worst date you’ve ever been on?
69. Do you have a go-to spot for first dates?
70. Do you follow anyone fun on YouTube?


71. Wanna play “Two Truths and a Lie”?
72. Wanna play “Never Have I ever”?
73. How many licks do you think it takes to get to the center of a Tootsie Pop?
74. How much wood do you think a woodchuck could chuck if a woodchuck could chuck wood?
75. Know any good tongue twisters?

That should be enough first date questions to last you quite a few Tinder matches! How have your first dates been so far? Have you ever asked a question that you wish you hadn’t asked at all? I’m sure I speak for everyone when I say that we’d love to hear about it in the comments below!

If you’re stuck on what to actually do on your first dates, check out this article for tons of creative ideas! And for even more ideas of great questions to ask your date, you can give this book a read as well. But if your first date problems go beyond what to do and what to say, you can always make use of my mini strategy sessions for some customized advice.

Until next time!

first date questions

4 Comments on “75 First Date Questions That Are Actually Interesting”

  1. I love these questions. I’m seeing a guy for the third time this weekend, and even though we’ve got past the awkward first date, there are definitely some questions on here I’d like to ask him!

    1. That’s such a good point! These questions are definitely not specific to a first date only. Enjoy! 😉

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