33 Questions to Ask on a Date

Katie Sweeney

Your stomach is filled with butterflies. You inwardly swoon as you notice that your legs are touching. "This second date is going wonderfully," you think as you sip a glass of jammy syrah. He finishes his story about backpacking through Thailand and suddenly things take a turn for the worst! An awkward uncomfortable silence fills the air, and you can’t think of anything to say. Have you experienced this dating conundrum, the everything-is-going-perfectly, then oh-no-I-can’t-think-of-anything-to-say mishap?

Unexpected silences that linger can quickly go from inconvenient to embarrassing and have the potential to ruin a great date, so it’s best to be prepared. That’s why whenever I go on a date, be it a first or a seventh, I have a list of conversation-starting questions in the back of my mind. The questions should be light, fun, and evoke interesting answers. Avoid polarizing topics like politics and religion, as you don’t want to end up in a heated debate. Need some inspiration? Here are 33 questions to ask on a date.

  1. What’s your favorite color?
  2. What sport did you play in high school?
  3. Where did you go to college?
  4. What were the holidays like in your house growing up?
  5. What’s your power animal?
  6. Where do you like to shop for clothes?
  7. What television shows are you into right now?
  8. What kind of cake do you eat on your birthday?
  9. Which sports teams do you follow?
  10. Are you a fan of the Harry Potter series? (Yes, I’ve asked this one on a date!)
  11. What was your most memorable vacation?
  12. Who in your family are you closest to?
  13. What was your most epic Halloween costume?
  14. Do you like to cook?
  15. Where have you traveled?
  16. If you had to drink only one spirit for the rest of your life, what would it be?
  17. Do you like to swim in the ocean?
  18. Do you collect anything?
  19. What’s your favorite book?
  20. Have you seen any good movies lately?
  21. What’s your favorite part of the Thanksgiving meal?
  22. Which Star Wars character do you most identify with?
  23. Where is your happy place?
  24. What does your perfect Saturday consist of?
  25. What is something you’re bad at?
  26. What are you dying to try?
  27. What is your hidden talent?
  28. What is your favorite TV show?
  29. When you were little, what did you want to be when you grew up?
  30. What Spotify station are you currently rocking?
  31. Are you a cat person or a dog person?
  32. What’s your morning coffee order?
  33. When’s your birthday?

Shop a few date-night essentials below.

What questions do you ask on a date? 

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