First Date Questions to Ask a Guy

A first date goes better when the conversation flows. These first date questions to ask a guy are easy to answer and fun to follow up on: his hobbies, the best trip he has taken, his perfect weekend, a skill he wants to learn and the food he would eat every day.

Skim the list before you go and keep three or four in mind. Share your own answers too so it feels like a conversation, not an interview. Every question is level 1, so nothing is too personal for a first meeting. If the date goes well, you will find deeper questions on our other pages for date two.

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  1. 1

    What do you do for fun when no one's watching?

  2. 2

    What's the best trip you've ever taken?

  3. 3

    What's your favorite way to spend a day off?

  4. 4

    What are you reading, watching or listening to right now?

  5. 5

    What's a food you could eat every day?

  6. 6

    What's a job you'd love to try for just one day?

  7. 7

    What's a skill you're secretly proud of?

  8. 8

    Are you a morning person or a night owl?

  9. 9

    What's the most spontaneous thing you've ever done?

  10. 10

    What's your favorite place in your city?

  11. 11

    What's the best piece of advice you've ever received?

  12. 12

    Dogs, cats or neither?

  13. 13

    What's a small thing that makes you really happy?

  14. 14

    What's the most interesting thing you've learned recently?

  15. 15

    What's your favorite way to spend a rainy day?

  16. 16

    What's the best meal you've ever had?

  17. 17

    Coffee date or Dessert date?

  18. 18

    Walk in the park or Dinner date?

  19. 19

    Texting or Calling?

  20. 20

    Plan ahead or Spontaneous?

  21. 21

    Talk about the past or Talk about the future?

  22. 22

    Split the bill or Take turns paying?

  23. 23

    Meet friends early or Wait a while?

  24. 24

    Would you rather go on a first date at a museum or at an amusement park?

  25. 25

    Would you rather have a long first date or a short sweet first date?

  26. 26

    Would you rather meet the parents early or meet the friends early?

  27. 27

    Would you rather text all day or talk on the phone at night?

  28. 28

    Would you rather go dancing or go hiking?

  29. 29

    What's the best thing you ate this week?

  30. 30

    What's your most-used emoji?

  31. 31

    What's your hidden talent?

  32. 32

    What's your favorite way to waste time?

  33. 33

    Sweet or salty snacks?

  34. 34

    What's the last show you binged?

  35. 35

    Beach vacation or city break?

  36. 36

    What's a song you know all the words to?

  37. 37

    What's your go-to pizza topping?

  38. 38

    What's a fun fact about you that few people know?

  39. 39

    What's the best app on your phone?

  40. 40

    What's your favorite smell?

  41. 41

    What's your dream job if money didn't matter?

  42. 42

    What's your favorite holiday tradition?

  43. 43

    What's your favorite board game?

  44. 44

    Morning workout or Evening workout?

  45. 45

    Instagram or TikTok?

  46. 46

    Spotify or YouTube?

  47. 47

    Sneakers or Boots?

  48. 48

    Chips or Popcorn?

  49. 49

    Superman or Batman?

  50. 50

    Harry Potter or Lord of the Rings?

What should I ask a guy on a first date?

Ask about his interests, friends, travel and what he enjoys doing on weekends. Open questions lead to better stories.

How do I avoid awkward silence?

Have a few questions ready and follow up on his answers with "what was that like?"

What topics should wait until later?

Exes, money and long-term plans are better for later dates.

Do these questions work for any first date?

Yes. Most of them work for anyone you are meeting for the first time.