20 Questions to Replace 'Small Talk' with 'Something Interesting' on a Date

Date night questions
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Human beings thrive on being perceived as interesting and desirable. Being able to keep a conversation going is absolutely key to building yourself into a desirable partner!

You want (and need) to be desirable for that potential new job, that big promotion and most importantly, your date night partner. Communication is the number one forward propeller of successful relationships. Couples that are able to keep things interesting have better sex, conversations and overall interactions. This article is for you if:

  • The recurrent lockdowns did absolutely nothing for your dating life
  • You want to connect deeper with your current partner
  • You always wonder what the ‘deep couples’ talk about

Below I’ve compiled questions that’ll not only make you appealing but will open you up to parts of your date that you otherwise would’ve taken most of your life trying to learn.
These questions have just enough depth to prompt interesting responses without being too pushy or invasive. The answers can lead to some pretty interesting places!

21 Date Night Questions

  1. Do you believe in the concept of “the one”?
  2. What made you decide to study (insert university major)?
  3. Who do you trust more than anybody else?
  4. When was the last time you really spoiled yourself?
  5. If your job isn’t your passion, then what is?
  6. What makes you feel happiest/lifts your mood?
  7. What’s your earliest childhood memory?
  8. When was the last time you stayed up late till the morning?
  9. What’s your oddest family tradition?
  10. If you were famous, what would it be for?
  11. What is your absolute dream job?
  12. Do you have a favourite dessert?
  13. How many languages do you speak?
  14. Then something a little weird…What season would you be?
  15. Another one…Would you go with the aliens if they beamed down on Earth?
  16. How do you really feel about your boss?
  17. Do you like ice cream? Which flavour?
  18. What’s your favourite scent?
  19. If you could write a book, what genre would it be in?
  20. Have you ever been told that you look like someone famous? Who was it?
  21. If money was no object, what would you do with your time and money?

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